Stay At Jimmy's
From
$327
/ night
Select dates to see prices and availability
From
$327
/ night
About this property
With a stay at Stay At Jimmy's in Woodstock, you'll be within a 15-minute drive of Quechee Gorge Bridge and Green Mountain National Forest. This bed & breakfast is 15.4 mi (24.8 km) from Killington Resort and 18.1 mi (29....
Business amenities
Free self parking is available onsite.
Dining
A complimentary continental breakfast is served daily from 7:00 AM to 9:00 AM.
Rooms
Make yourself at home in one of the 3 individually decorated guestrooms, featuring kitchenettes. 55-inch Smart televisions with digital programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms have jetted bathtubs and rainfall showerheads. Conveniences include microwaves, housekeeping is provided on request, and irons/ironing boards can be requested.
Location
With a stay at Stay At Jimmy's in Woodstock, you'll be within a 15-minute drive of Quechee Gorge Bridge and Green Mountain National Forest. This bed & breakfast is 15.4 mi (24.8 km) from Killington Resort and 18.1 mi (29.1 km) from Dartmouth College.
What's nearby
Mt Ascutney Hospital and Health Center Primary Care - Woodstock(0.2 miles)
Ottauquechee Health Center(0.2 miles)
Red Wagon Toy Company(0.4 miles)
Billings Park and Trail(0.5 miles)
Dana House Museum(0.5 miles)
Middle Covered Bridge(0.6 miles)
Marsh-Billings-Rockefeller National Historical Park(0.7 miles)
Woodstock Town Hall Theatre(0.7 miles)
Mt. Peg Ski Trail(0.7 miles)
Upper Mountain Road(0.8 miles)
Billings Farm and Museum(0.8 miles)
Mountain Road(0.8 miles)
Stewardship Trail(0.8 miles)
Upper Cross(1 miles)
Sugar House Trail(1.1 miles)
Lebanon, NH (LEB-Lebanon Municipal)(15.1 miles)
Springfield, VT (VSF-Hartness State)(22.8 miles)
Rutland, VT (RUT-Rutland Southern Vermont Regional)(37.8 miles)
Parking
Free Wi-Fi
Breakfast in the Room
Garden
Free Parking
Parking Onsite
Location
45 Pleasant Street, Woodstock, Vermont, United States of America
Mt Ascutney Hospital and Health Center Primary Care - Woodstock (0.2 miles)
Ottauquechee Health Center (0.2 miles)
Red Wagon Toy Company (0.4 miles)
Billings Park and Trail (0.5 miles)
Dana House Museum (0.5 miles)
Middle Covered Bridge (0.6 miles)
Room options
8
Signature Suite, Garden View
Room details
1 King Bed
Sleeps 2
470 ft²
Air ConditioningHeated FloorHeatingIndoor Private Spa TubPrivate Spa Tub
9
Signature Double Room, Garden View
Room details
1 King Bed
Sleeps 2
177 ft²
Air ConditioningHeatingWi-Fi (Free)
8
Signature Double Room, Courtyard View
Room details
1 King Bed
Sleeps 2
180 ft²
Air ConditioningHeatingWi-Fi (Free)
Guest reviews of Stay At Jimmy's
9.7
Exceptional
Based on 72 verified reviews
What guests think
AI-generated summary based on recent guest reviews
At Stay At Jimmy's, travellers praise warm, hands-on hosts and thoughtfully designed, modern rooms stocked with generous amenities, while the convenient, walkable location and on-site parking make exploring Woodstock easy for both short visits and longer stays.
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What guests think
At Stay At Jimmy's, travellers praise warm, hands-on hosts and thoughtfully designed, modern rooms stocked with generous amenities, while the convenient, walkable location and on-site parking make exploring Woodstock easy for both short visits and longer stays.
Reviews consistently note spotless conditions and comfortable beds. Guests appreciate the in-room breakfast pastries, snacks, and drinks, with some suites featuring large tubs or rainfall showers. The wraparound porch, fire pits, and dog-friendly policy add to the relaxed, homey feel. Expect a welcoming, well-kept base near town with thoughtful extras.
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AI-generated summary based on recent guest reviews
Facilities
On-site parking is convenient, and guests enjoy the wraparound porch and fire pits. The property is dog-friendly.
Related guest reviews
10
David
Sep 3, 2025
·
Stayed 1 night
What a wonderful and unique property! We were met by John (partner of Jimmy) and he very affable and willing to help. Wonderful breakfast bakeries were already awaiting. The room was awesome-highly functional and also quirky in a good way. The wrap around porch is gorgeous with nice areas to sit and chat. We would definitely book with Stay at Jimmy’s again!
What a wonderful and unique property! We were met by John (partner of Jimmy) and he very affable and willing to help. Wonderful breakfast bakeries were already awaiting. The room was awesome-highly functional and also quirky in a good way. The wrap around porch is gorgeous with nice areas to sit and chat. We would definitely book with Stay at Jimmy’s again!
10
MacKenzie
Aug 19, 2024
·
Stayed 1 night
Jimmy and John were so welcoming and made our stay in Woodstock exceptional! Not only were they kind to us, but also to our dog who loved her time at the property as well. We can't wait to go back!
Jimmy and John were so welcoming and made our stay in Woodstock exceptional! Not only were they kind to us, but also to our dog who loved her time at the property as well. We can't wait to go back!
10
Gary
May 13, 2025
·
Stayed 1 night
4/28/25 Stay: Exceeded expectations everywhere. Owners were very accessible and greeted us to make sure we had everything to make our experience memorable. Location was fabulous as very safe and walkable to anywhere in town. Convenient parking on premise. Room access was secure, comfortable, extremely clean, and appointed with every amenity you could think of and more. I will stay at Jimmy’s anytime I visit Woodstock and highly recommend you do so as well.
4/28/25 Stay: Exceeded expectations everywhere. Owners were very accessible and greeted us to make sure we had everything to make our experience memorable. Location was fabulous as very safe and walkable to anywhere in town. Convenient parking on premise. Room access was secure, comfortable, extremely clean, and appointed with every amenity you could think of and more. I will stay at Jimmy’s anytime I visit Woodstock and highly recommend you do so as well.
10
John
Jun 7, 2024
·
Stayed 1 night
Our stay at Jimmy’s met all our expectations that we had hoped for in Woodstock. The accommodation is conveniently situated close to the heart of town and once we had parked our car it was easy to walk to the restaurants and shops. The room was impeccably appointed and spotlessly clean. Our hosts were extremely hospitable and personally welcomed us upon our arrival. Our stay was short and sweet but we will return when next in Woodstock. We would highly recommend a stay at Jimmy’s. Wonderful ( and it is pet friendly !).
Our stay at Jimmy’s met all our expectations that we had hoped for in Woodstock. The accommodation is conveniently situated close to the heart of town and once we had parked our car it was easy to walk to the restaurants and shops. The room was impeccably appointed and spotlessly clean. Our hosts were extremely hospitable and personally welcomed us upon our arrival. Our stay was short and sweet but we will return when next in Woodstock. We would highly recommend a stay at Jimmy’s. Wonderful ( and it is pet friendly !).
10
Monique
Mar 31, 2025
·
Stayed 1 night
Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.
Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.
10
kathryn
Oct 3, 2024
·
Stayed 2 nights
We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.
We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.
10
kirk
Feb 21, 2025
·
Stayed 4 nights
We spent a wonderful week at Stay at Jimmy’s, with our dog Sofia (they are super dog friendly) and it was the perfect escape. From the moment we arrived, the hospitality was top-notch. The Relax Room was absolutely amazing—the whirlpool tub was the best we’ve ever used, making it the ideal place to unwind. Every morning, we were treated to fresh-baked goods, a great selection of teas, coffee, and soft drinks, which made us feel right at home. The attention to detail in the interior design was impressive—every space was beautifully curated, warm, and inviting. One of the most thoughtful touches was Jimmy surprising my wife with a birthday card during our stay, making the experience even more special. She also took a fantastic on-site yoga class, which she absolutely loved. If you’re looking for a peaceful, rejuvenating getaway with incredible hospitality, Stay at Jimmy’s in Woodstock, VT is the perfect choice. We can’t wait to come back!
We spent a wonderful week at Stay at Jimmy’s, with our dog Sofia (they are super dog friendly) and it was the perfect escape. From the moment we arrived, the hospitality was top-notch. The Relax Room was absolutely amazing—the whirlpool tub was the best we’ve ever used, making it the ideal place to unwind. Every morning, we were treated to fresh-baked goods, a great selection of teas, coffee, and soft drinks, which made us feel right at home. The attention to detail in the interior design was impressive—every space was beautifully curated, warm, and inviting. One of the most thoughtful touches was Jimmy surprising my wife with a birthday card during our stay, making the experience even more special. She also took a fantastic on-site yoga class, which she absolutely loved. If you’re looking for a peaceful, rejuvenating getaway with incredible hospitality, Stay at Jimmy’s in Woodstock, VT is the perfect choice. We can’t wait to come back!
10
Elise
Sep 9, 2024
·
Stayed 1 night
Jimmy’s combines quaint and modern flawlessly! The wrap around porch was perfect for our rainy evening (several fire pits available too).
Jimmy’s combines quaint and modern flawlessly! The wrap around porch was perfect for our rainy evening (several fire pits available too).
10
CLARA
Oct 20, 2025
·
Stayed 1 night
This property is conveniently located with on site parking. It is about 10 mins walk into downtown, there are restaurants, coffee shops and ice cream shops. Room was great, everything you needed was thought of. I would recommend it very much.
This property is conveniently located with on site parking. It is about 10 mins walk into downtown, there are restaurants, coffee shops and ice cream shops. Room was great, everything you needed was thought of. I would recommend it very much.
10
Laura
Aug 18, 2024
·
Stayed 2 nights
Our stay was AMAZING! Jimmy and John are the perfect hosts. The fresh fruit and baked items, the beautiful grounds, the private fire pit, the comfortable apartment, the perfect location, and the way our hosts made us feel so comfortable, well, we just truly hated to leave. Thank you Jimmy and John for an amazing, (too brief), stay at your BnB!!!
Our stay was AMAZING! Jimmy and John are the perfect hosts. The fresh fruit and baked items, the beautiful grounds, the private fire pit, the comfortable apartment, the perfect location, and the way our hosts made us feel so comfortable, well, we just truly hated to leave. Thank you Jimmy and John for an amazing, (too brief), stay at your BnB!!!
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AI-generated summary based on recent guest reviews
Cleanliness
Cleanliness is consistently praised, with rooms described as spotless and well maintained.
Related guest reviews
10
Benjamin
Jul 14, 2025
·
Stayed 3 nights
Stylish, clean, comfortable, and in the perfect location to start and end the day. The owners were lovely and accommodating, and the room was a treat for the eyes and a balm for the body. Couldn’t recommend more!
Stylish, clean, comfortable, and in the perfect location to start and end the day. The owners were lovely and accommodating, and the room was a treat for the eyes and a balm for the body. Couldn’t recommend more!
10
Eloise
Nov 2, 2024
·
Stayed 1 night
Il s’agit littéralement du meilleur hôtel que nous avons fait durant notre séjour ! Tout est extrêmement propre et bien pensé et les petites attentions étaient nombreuses… c’est un endroit dans lequel on se sent safe et très bien accueillis ! Merci infiniment à John et Jimmy pour cette pépite ! Si vous devez séjourner à Woodstock n’hésitez pas, c’est ici !
Il s’agit littéralement du meilleur hôtel que nous avons fait durant notre séjour ! Tout est extrêmement propre et bien pensé et les petites attentions étaient nombreuses… c’est un endroit dans lequel on se sent safe et très bien accueillis ! Merci infiniment à John et Jimmy pour cette pépite ! Si vous devez séjourner à Woodstock n’hésitez pas, c’est ici !
10
Catherine
Oct 2, 2025
·
Stayed 2 nights
A really delightful stay hosted by stellar hosts! Great location only a few minutes walk to the centre of town. Property was spotless and everything within screams quality from the bedding to the bathroom tv art……. My husband over indulged on the banana walnut bread as it was so scrumptious, lots of goodies for those with a sweet tooth, all top notch. Would 100% stay here again. The only thing to note is that in October (I’m not sure about other months)you’d better prebook restaurants a week or so ahead as it’s busy.
A really delightful stay hosted by stellar hosts! Great location only a few minutes walk to the centre of town. Property was spotless and everything within screams quality from the bedding to the bathroom tv art……. My husband over indulged on the banana walnut bread as it was so scrumptious, lots of goodies for those with a sweet tooth, all top notch. Would 100% stay here again. The only thing to note is that in October (I’m not sure about other months)you’d better prebook restaurants a week or so ahead as it’s busy.
10
Daniele
Jul 22, 2024
·
Stayed 1 night
My wife and I recently stayed at "Stay at Jimmy\'s", and it was a delightful experience. The rooms were impeccably clean and tastefully decorated, providing a cozy and inviting atmosphere. Jimmy & John\'s hospitality was top-notch, with a friendly and accommodating demeanor that made us feel right at home. "Stay at Jimmy\'s" exceeded our expectations, and I would highly recommend it to anyone seeking a charming and comfortable stay.
My wife and I recently stayed at "Stay at Jimmy\'s", and it was a delightful experience. The rooms were impeccably clean and tastefully decorated, providing a cozy and inviting atmosphere. Jimmy & John\'s hospitality was top-notch, with a friendly and accommodating demeanor that made us feel right at home. "Stay at Jimmy\'s" exceeded our expectations, and I would highly recommend it to anyone seeking a charming and comfortable stay.
10
Abigail
Dec 9, 2024
·
Stayed 1 night
Our stay here was absolutely amazing! As soon as we walked in, we knew that we picked the right place. It was safe, clean and so close to downtown. John and Jimmy were the sweetest and made us feel right at home. We can’t recommend this place enough and will definitely be back!!
Our stay here was absolutely amazing! As soon as we walked in, we knew that we picked the right place. It was safe, clean and so close to downtown. John and Jimmy were the sweetest and made us feel right at home. We can’t recommend this place enough and will definitely be back!!
10
Hilary
Jul 9, 2025
·
Stayed 1 night
Super modern, comfortable, and clean. Jimmy provided everything we could possibly need. Highly recommend!
Super modern, comfortable, and clean. Jimmy provided everything we could possibly need. Highly recommend!
10
Gary
May 13, 2025
·
Stayed 1 night
4/28/25 Stay: Exceeded expectations everywhere. Owners were very accessible and greeted us to make sure we had everything to make our experience memorable. Location was fabulous as very safe and walkable to anywhere in town. Convenient parking on premise. Room access was secure, comfortable, extremely clean, and appointed with every amenity you could think of and more. I will stay at Jimmy’s anytime I visit Woodstock and highly recommend you do so as well.
4/28/25 Stay: Exceeded expectations everywhere. Owners were very accessible and greeted us to make sure we had everything to make our experience memorable. Location was fabulous as very safe and walkable to anywhere in town. Convenient parking on premise. Room access was secure, comfortable, extremely clean, and appointed with every amenity you could think of and more. I will stay at Jimmy’s anytime I visit Woodstock and highly recommend you do so as well.
10
John
Jun 7, 2024
·
Stayed 1 night
Our stay at Jimmy’s met all our expectations that we had hoped for in Woodstock. The accommodation is conveniently situated close to the heart of town and once we had parked our car it was easy to walk to the restaurants and shops. The room was impeccably appointed and spotlessly clean. Our hosts were extremely hospitable and personally welcomed us upon our arrival. Our stay was short and sweet but we will return when next in Woodstock. We would highly recommend a stay at Jimmy’s. Wonderful ( and it is pet friendly !).
Our stay at Jimmy’s met all our expectations that we had hoped for in Woodstock. The accommodation is conveniently situated close to the heart of town and once we had parked our car it was easy to walk to the restaurants and shops. The room was impeccably appointed and spotlessly clean. Our hosts were extremely hospitable and personally welcomed us upon our arrival. Our stay was short and sweet but we will return when next in Woodstock. We would highly recommend a stay at Jimmy’s. Wonderful ( and it is pet friendly !).
10
Monique
Mar 31, 2025
·
Stayed 1 night
Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.
Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.
10
Winnett
Jun 23, 2024
·
Stayed 1 night
We had a great time at Stay at Jimmy’s! The rooms are well appointed and very comfortable. Our bathroom had a huge tub and beautiful shower. We loved walking into town to get coffee! The rooms were very clean and modern. We will be back thank you!
We had a great time at Stay at Jimmy’s! The rooms are well appointed and very comfortable. Our bathroom had a huge tub and beautiful shower. We loved walking into town to get coffee! The rooms were very clean and modern. We will be back thank you!
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AI-generated summary based on recent guest reviews
Rooms
Rooms are modern, comfortable, and thoughtfully designed, with many noting quality decor and well-appointed amenities. Some suites include features like large tubs, rainfall showers, or private entrances, and several guests found the spaces quiet.
Related guest reviews
10
Erin
Oct 7, 2025
·
Stayed 1 night
We were welcomed by John when we checked in. It was our 25th anniversary and in our room was the sweetest card and balloons to honor the occasion. So extremely thoughtful! The room was adorable and very comfortable. It had been outfitted with all the amenities you can think of…pastries and snacks, board games, toiletries, and a full kitchen. The only thing I regret is not staying longer in this charming B and B! We will absolutely be back when we visit Woodstock!
We were welcomed by John when we checked in. It was our 25th anniversary and in our room was the sweetest card and balloons to honor the occasion. So extremely thoughtful! The room was adorable and very comfortable. It had been outfitted with all the amenities you can think of…pastries and snacks, board games, toiletries, and a full kitchen. The only thing I regret is not staying longer in this charming B and B! We will absolutely be back when we visit Woodstock!
10
Benjamin
Jul 14, 2025
·
Stayed 3 nights
Stylish, clean, comfortable, and in the perfect location to start and end the day. The owners were lovely and accommodating, and the room was a treat for the eyes and a balm for the body. Couldn’t recommend more!
Stylish, clean, comfortable, and in the perfect location to start and end the day. The owners were lovely and accommodating, and the room was a treat for the eyes and a balm for the body. Couldn’t recommend more!
10
Dennis
Nov 18, 2024
·
Stayed 1 night
Wow! Loved our visit at Stay at Jimmy's. Room was beautifully decorated and supplied with everything we needed. Location was perfect for exploring Woodstock. We had excellent communication from John and Jimmy. A bonus for us was the EV charging station across the street.
Wow! Loved our visit at Stay at Jimmy's. Room was beautifully decorated and supplied with everything we needed. Location was perfect for exploring Woodstock. We had excellent communication from John and Jimmy. A bonus for us was the EV charging station across the street.
10
Hilary
Jul 9, 2025
·
Stayed 1 night
Super modern, comfortable, and clean. Jimmy provided everything we could possibly need. Highly recommend!
Super modern, comfortable, and clean. Jimmy provided everything we could possibly need. Highly recommend!
10
Bonnie
Oct 29, 2024
·
Stayed 1 night
I loved the attention to detail. We stay in a decent number of inns, B&Bs and hotels - most of which are excellent. This is the only one with decent tea AND agave. Some other distinguishing features: bidet, lots of snacks & refreshments, baked goods for breakfast already in room, adjustable-light mirror and embossed toilet paper. I loved that the rooms were not colonial decor with flowered bedding and traditional furniture - so common in this area. Very clean with the guest in mind!
I loved the attention to detail. We stay in a decent number of inns, B&Bs and hotels - most of which are excellent. This is the only one with decent tea AND agave. Some other distinguishing features: bidet, lots of snacks & refreshments, baked goods for breakfast already in room, adjustable-light mirror and embossed toilet paper. I loved that the rooms were not colonial decor with flowered bedding and traditional furniture - so common in this area. Very clean with the guest in mind!
10
Monique
Mar 31, 2025
·
Stayed 1 night
Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.
Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.
10
kathryn
Oct 3, 2024
·
Stayed 2 nights
We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.
We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.
10
Winnett
Jun 23, 2024
·
Stayed 1 night
We had a great time at Stay at Jimmy’s! The rooms are well appointed and very comfortable. Our bathroom had a huge tub and beautiful shower. We loved walking into town to get coffee! The rooms were very clean and modern. We will be back thank you!
We had a great time at Stay at Jimmy’s! The rooms are well appointed and very comfortable. Our bathroom had a huge tub and beautiful shower. We loved walking into town to get coffee! The rooms were very clean and modern. We will be back thank you!
10
Jessica
Jan 15, 2025
·
Stayed 2 nights
The owners of Jimmy's went above and beyond in every way and the room was fantastic!
The owners of Jimmy's went above and beyond in every way and the room was fantastic!
10
Julie
Aug 28, 2025
·
Stayed 1 night
Jimmy's was fantastic! I really want to have Jimmy design my house. Every detail was taken care of, comfortable bed, and decor was so fun! Loved the rainfall shower head. We met John, who was so warm and welcoming. Also met Mable and Matilda who were sweeties. We only stayed one night and wished that we had been able to stay longer. The location is very convenient.
Jimmy's was fantastic! I really want to have Jimmy design my house. Every detail was taken care of, comfortable bed, and decor was so fun! Loved the rainfall shower head. We met John, who was so warm and welcoming. Also met Mable and Matilda who were sweeties. We only stayed one night and wished that we had been able to stay longer. The location is very convenient.
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AI-generated summary based on recent guest reviews
Service
Hosts Jimmy and John are widely praised as welcoming, attentive, and highly communicative, often adding thoughtful personal touches. Check-in is smooth, and the team is accessible and accommodating throughout stays.
Related guest reviews
10
Erin
Oct 7, 2025
·
Stayed 1 night
We were welcomed by John when we checked in. It was our 25th anniversary and in our room was the sweetest card and balloons to honor the occasion. So extremely thoughtful! The room was adorable and very comfortable. It had been outfitted with all the amenities you can think of…pastries and snacks, board games, toiletries, and a full kitchen. The only thing I regret is not staying longer in this charming B and B! We will absolutely be back when we visit Woodstock!
We were welcomed by John when we checked in. It was our 25th anniversary and in our room was the sweetest card and balloons to honor the occasion. So extremely thoughtful! The room was adorable and very comfortable. It had been outfitted with all the amenities you can think of…pastries and snacks, board games, toiletries, and a full kitchen. The only thing I regret is not staying longer in this charming B and B! We will absolutely be back when we visit Woodstock!
10
John
Sep 2, 2024
·
Stayed 2 nights
Charming and attentive hosts. Perfect spot to relax and enjoy Woodstock. I highly recommend Stay at Jimmys
Charming and attentive hosts. Perfect spot to relax and enjoy Woodstock. I highly recommend Stay at Jimmys
10
David
Sep 3, 2025
·
Stayed 1 night
What a wonderful and unique property! We were met by John (partner of Jimmy) and he very affable and willing to help. Wonderful breakfast bakeries were already awaiting. The room was awesome-highly functional and also quirky in a good way. The wrap around porch is gorgeous with nice areas to sit and chat. We would definitely book with Stay at Jimmy’s again!
What a wonderful and unique property! We were met by John (partner of Jimmy) and he very affable and willing to help. Wonderful breakfast bakeries were already awaiting. The room was awesome-highly functional and also quirky in a good way. The wrap around porch is gorgeous with nice areas to sit and chat. We would definitely book with Stay at Jimmy’s again!
10
Frederick
Feb 15, 2025
·
Stayed 1 night
Good ownership, very helpful
Good ownership, very helpful
10
Abigail
Dec 9, 2024
·
Stayed 1 night
Our stay here was absolutely amazing! As soon as we walked in, we knew that we picked the right place. It was safe, clean and so close to downtown. John and Jimmy were the sweetest and made us feel right at home. We can’t recommend this place enough and will definitely be back!!
Our stay here was absolutely amazing! As soon as we walked in, we knew that we picked the right place. It was safe, clean and so close to downtown. John and Jimmy were the sweetest and made us feel right at home. We can’t recommend this place enough and will definitely be back!!
10
Susan
Jan 20, 2025
·
Stayed 1 night
Stay at Jimmys is exceptional! From the second you pull into the lot you are greeted with pure joy. Jimmy came out and introduced himself welcoming us to his beautiful Inn. I travel around the globe and have never been welcomed this beautifully in all my life. The property is clean, peaceful, fabulously decorated. It’s so comfortable and welcoming. We didn’t want to leave! And guess what? Jimmy told us we could stay as long as we wanted the day of check out beaches they didn’t have anyone coming in after us. Who does that?!? If we weren’t worried about the snow storm we would definitely have stayed a few more hours. This is our new go to when visit family in VT. Jimmy and John we’ll see you again.
Stay at Jimmys is exceptional! From the second you pull into the lot you are greeted with pure joy. Jimmy came out and introduced himself welcoming us to his beautiful Inn. I travel around the globe and have never been welcomed this beautifully in all my life. The property is clean, peaceful, fabulously decorated. It’s so comfortable and welcoming. We didn’t want to leave! And guess what? Jimmy told us we could stay as long as we wanted the day of check out beaches they didn’t have anyone coming in after us. Who does that?!? If we weren’t worried about the snow storm we would definitely have stayed a few more hours. This is our new go to when visit family in VT. Jimmy and John we’ll see you again.
10
Gary
May 13, 2025
·
Stayed 1 night
4/28/25 Stay: Exceeded expectations everywhere. Owners were very accessible and greeted us to make sure we had everything to make our experience memorable. Location was fabulous as very safe and walkable to anywhere in town. Convenient parking on premise. Room access was secure, comfortable, extremely clean, and appointed with every amenity you could think of and more. I will stay at Jimmy’s anytime I visit Woodstock and highly recommend you do so as well.
4/28/25 Stay: Exceeded expectations everywhere. Owners were very accessible and greeted us to make sure we had everything to make our experience memorable. Location was fabulous as very safe and walkable to anywhere in town. Convenient parking on premise. Room access was secure, comfortable, extremely clean, and appointed with every amenity you could think of and more. I will stay at Jimmy’s anytime I visit Woodstock and highly recommend you do so as well.
10
kathryn
Oct 3, 2024
·
Stayed 2 nights
We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.
We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.
10
Sandra
Jun 15, 2025
·
Stayed 1 night
Jimmy and John were amazing hosts! Very communicative!
Jimmy and John were amazing hosts! Very communicative!
10
Julie
Aug 28, 2025
·
Stayed 1 night
Jimmy's was fantastic! I really want to have Jimmy design my house. Every detail was taken care of, comfortable bed, and decor was so fun! Loved the rainfall shower head. We met John, who was so warm and welcoming. Also met Mable and Matilda who were sweeties. We only stayed one night and wished that we had been able to stay longer. The location is very convenient.
Jimmy's was fantastic! I really want to have Jimmy design my house. Every detail was taken care of, comfortable bed, and decor was so fun! Loved the rainfall shower head. We met John, who was so warm and welcoming. Also met Mable and Matilda who were sweeties. We only stayed one night and wished that we had been able to stay longer. The location is very convenient.
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AI-generated summary based on recent guest reviews
Location
Convenient and walkable to downtown Woodstock, restaurants, and shops. Several guests also mention feeling safe.
Related guest reviews
10
Benjamin
Jul 14, 2025
·
Stayed 3 nights
Stylish, clean, comfortable, and in the perfect location to start and end the day. The owners were lovely and accommodating, and the room was a treat for the eyes and a balm for the body. Couldn’t recommend more!
Stylish, clean, comfortable, and in the perfect location to start and end the day. The owners were lovely and accommodating, and the room was a treat for the eyes and a balm for the body. Couldn’t recommend more!
10
Catherine
Oct 2, 2025
·
Stayed 2 nights
A really delightful stay hosted by stellar hosts! Great location only a few minutes walk to the centre of town. Property was spotless and everything within screams quality from the bedding to the bathroom tv art……. My husband over indulged on the banana walnut bread as it was so scrumptious, lots of goodies for those with a sweet tooth, all top notch. Would 100% stay here again. The only thing to note is that in October (I’m not sure about other months)you’d better prebook restaurants a week or so ahead as it’s busy.
A really delightful stay hosted by stellar hosts! Great location only a few minutes walk to the centre of town. Property was spotless and everything within screams quality from the bedding to the bathroom tv art……. My husband over indulged on the banana walnut bread as it was so scrumptious, lots of goodies for those with a sweet tooth, all top notch. Would 100% stay here again. The only thing to note is that in October (I’m not sure about other months)you’d better prebook restaurants a week or so ahead as it’s busy.
10
Abigail
Dec 9, 2024
·
Stayed 1 night
Our stay here was absolutely amazing! As soon as we walked in, we knew that we picked the right place. It was safe, clean and so close to downtown. John and Jimmy were the sweetest and made us feel right at home. We can’t recommend this place enough and will definitely be back!!
Our stay here was absolutely amazing! As soon as we walked in, we knew that we picked the right place. It was safe, clean and so close to downtown. John and Jimmy were the sweetest and made us feel right at home. We can’t recommend this place enough and will definitely be back!!
10
Gary
Aug 9, 2025
·
Stayed 1 night
Short walk to downtown Woodstock. Breakfast was included and provided in our room.
Short walk to downtown Woodstock. Breakfast was included and provided in our room.
10
Gary
May 13, 2025
·
Stayed 1 night
4/28/25 Stay: Exceeded expectations everywhere. Owners were very accessible and greeted us to make sure we had everything to make our experience memorable. Location was fabulous as very safe and walkable to anywhere in town. Convenient parking on premise. Room access was secure, comfortable, extremely clean, and appointed with every amenity you could think of and more. I will stay at Jimmy’s anytime I visit Woodstock and highly recommend you do so as well.
4/28/25 Stay: Exceeded expectations everywhere. Owners were very accessible and greeted us to make sure we had everything to make our experience memorable. Location was fabulous as very safe and walkable to anywhere in town. Convenient parking on premise. Room access was secure, comfortable, extremely clean, and appointed with every amenity you could think of and more. I will stay at Jimmy’s anytime I visit Woodstock and highly recommend you do so as well.
10
John
Jun 7, 2024
·
Stayed 1 night
Our stay at Jimmy’s met all our expectations that we had hoped for in Woodstock. The accommodation is conveniently situated close to the heart of town and once we had parked our car it was easy to walk to the restaurants and shops. The room was impeccably appointed and spotlessly clean. Our hosts were extremely hospitable and personally welcomed us upon our arrival. Our stay was short and sweet but we will return when next in Woodstock. We would highly recommend a stay at Jimmy’s. Wonderful ( and it is pet friendly !).
Our stay at Jimmy’s met all our expectations that we had hoped for in Woodstock. The accommodation is conveniently situated close to the heart of town and once we had parked our car it was easy to walk to the restaurants and shops. The room was impeccably appointed and spotlessly clean. Our hosts were extremely hospitable and personally welcomed us upon our arrival. Our stay was short and sweet but we will return when next in Woodstock. We would highly recommend a stay at Jimmy’s. Wonderful ( and it is pet friendly !).
10
kathryn
Oct 3, 2024
·
Stayed 2 nights
We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.
We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.
10
Winnett
Jun 23, 2024
·
Stayed 1 night
We had a great time at Stay at Jimmy’s! The rooms are well appointed and very comfortable. Our bathroom had a huge tub and beautiful shower. We loved walking into town to get coffee! The rooms were very clean and modern. We will be back thank you!
We had a great time at Stay at Jimmy’s! The rooms are well appointed and very comfortable. Our bathroom had a huge tub and beautiful shower. We loved walking into town to get coffee! The rooms were very clean and modern. We will be back thank you!
10
CLARA
Oct 20, 2025
·
Stayed 1 night
This property is conveniently located with on site parking. It is about 10 mins walk into downtown, there are restaurants, coffee shops and ice cream shops. Room was great, everything you needed was thought of. I would recommend it very much.
This property is conveniently located with on site parking. It is about 10 mins walk into downtown, there are restaurants, coffee shops and ice cream shops. Room was great, everything you needed was thought of. I would recommend it very much.
10
Julie
Aug 28, 2025
·
Stayed 1 night
Jimmy's was fantastic! I really want to have Jimmy design my house. Every detail was taken care of, comfortable bed, and decor was so fun! Loved the rainfall shower head. We met John, who was so warm and welcoming. Also met Mable and Matilda who were sweeties. We only stayed one night and wished that we had been able to stay longer. The location is very convenient.
Jimmy's was fantastic! I really want to have Jimmy design my house. Every detail was taken care of, comfortable bed, and decor was so fun! Loved the rainfall shower head. We met John, who was so warm and welcoming. Also met Mable and Matilda who were sweeties. We only stayed one night and wished that we had been able to stay longer. The location is very convenient.
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AI-generated summary based on recent guest reviews
Dining
Guests consistently enjoy in-room breakfast pastries, baked goods, snacks, and drinks, with good coffee and tea. This setup is appreciated even though it is not a traditional sit-down breakfast.
Related guest reviews
10
Erin
Oct 7, 2025
·
Stayed 1 night
We were welcomed by John when we checked in. It was our 25th anniversary and in our room was the sweetest card and balloons to honor the occasion. So extremely thoughtful! The room was adorable and very comfortable. It had been outfitted with all the amenities you can think of…pastries and snacks, board games, toiletries, and a full kitchen. The only thing I regret is not staying longer in this charming B and B! We will absolutely be back when we visit Woodstock!
We were welcomed by John when we checked in. It was our 25th anniversary and in our room was the sweetest card and balloons to honor the occasion. So extremely thoughtful! The room was adorable and very comfortable. It had been outfitted with all the amenities you can think of…pastries and snacks, board games, toiletries, and a full kitchen. The only thing I regret is not staying longer in this charming B and B! We will absolutely be back when we visit Woodstock!
10
Robert
Jun 27, 2025
·
Stayed 1 night
Every little detail is taken care of... Every thought for the customers convenience. Q-tips! What hotel supplies Q-tips? We were lucky enough to meet Jimmy... Nice guy, very welcoming. Snacks, beverages... Fresh muffins and coffee. I can't say enough about how wonderful our stay was... Price was very low for what you get. Highly recommend
Every little detail is taken care of... Every thought for the customers convenience. Q-tips! What hotel supplies Q-tips? We were lucky enough to meet Jimmy... Nice guy, very welcoming. Snacks, beverages... Fresh muffins and coffee. I can't say enough about how wonderful our stay was... Price was very low for what you get. Highly recommend
10
David
Sep 3, 2025
·
Stayed 1 night
What a wonderful and unique property! We were met by John (partner of Jimmy) and he very affable and willing to help. Wonderful breakfast bakeries were already awaiting. The room was awesome-highly functional and also quirky in a good way. The wrap around porch is gorgeous with nice areas to sit and chat. We would definitely book with Stay at Jimmy’s again!
What a wonderful and unique property! We were met by John (partner of Jimmy) and he very affable and willing to help. Wonderful breakfast bakeries were already awaiting. The room was awesome-highly functional and also quirky in a good way. The wrap around porch is gorgeous with nice areas to sit and chat. We would definitely book with Stay at Jimmy’s again!
10
Bonnie
Oct 29, 2024
·
Stayed 1 night
I loved the attention to detail. We stay in a decent number of inns, B&Bs and hotels - most of which are excellent. This is the only one with decent tea AND agave. Some other distinguishing features: bidet, lots of snacks & refreshments, baked goods for breakfast already in room, adjustable-light mirror and embossed toilet paper. I loved that the rooms were not colonial decor with flowered bedding and traditional furniture - so common in this area. Very clean with the guest in mind!
I loved the attention to detail. We stay in a decent number of inns, B&Bs and hotels - most of which are excellent. This is the only one with decent tea AND agave. Some other distinguishing features: bidet, lots of snacks & refreshments, baked goods for breakfast already in room, adjustable-light mirror and embossed toilet paper. I loved that the rooms were not colonial decor with flowered bedding and traditional furniture - so common in this area. Very clean with the guest in mind!
10
Gary
Aug 9, 2025
·
Stayed 1 night
Short walk to downtown Woodstock. Breakfast was included and provided in our room.
Short walk to downtown Woodstock. Breakfast was included and provided in our room.
10
kathryn
Oct 3, 2024
·
Stayed 2 nights
We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.
We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.
10
kirk
Feb 21, 2025
·
Stayed 4 nights
We spent a wonderful week at Stay at Jimmy’s, with our dog Sofia (they are super dog friendly) and it was the perfect escape. From the moment we arrived, the hospitality was top-notch. The Relax Room was absolutely amazing—the whirlpool tub was the best we’ve ever used, making it the ideal place to unwind. Every morning, we were treated to fresh-baked goods, a great selection of teas, coffee, and soft drinks, which made us feel right at home. The attention to detail in the interior design was impressive—every space was beautifully curated, warm, and inviting. One of the most thoughtful touches was Jimmy surprising my wife with a birthday card during our stay, making the experience even more special. She also took a fantastic on-site yoga class, which she absolutely loved. If you’re looking for a peaceful, rejuvenating getaway with incredible hospitality, Stay at Jimmy’s in Woodstock, VT is the perfect choice. We can’t wait to come back!
We spent a wonderful week at Stay at Jimmy’s, with our dog Sofia (they are super dog friendly) and it was the perfect escape. From the moment we arrived, the hospitality was top-notch. The Relax Room was absolutely amazing—the whirlpool tub was the best we’ve ever used, making it the ideal place to unwind. Every morning, we were treated to fresh-baked goods, a great selection of teas, coffee, and soft drinks, which made us feel right at home. The attention to detail in the interior design was impressive—every space was beautifully curated, warm, and inviting. One of the most thoughtful touches was Jimmy surprising my wife with a birthday card during our stay, making the experience even more special. She also took a fantastic on-site yoga class, which she absolutely loved. If you’re looking for a peaceful, rejuvenating getaway with incredible hospitality, Stay at Jimmy’s in Woodstock, VT is the perfect choice. We can’t wait to come back!
10
Laura
Aug 18, 2024
·
Stayed 2 nights
Our stay was AMAZING! Jimmy and John are the perfect hosts. The fresh fruit and baked items, the beautiful grounds, the private fire pit, the comfortable apartment, the perfect location, and the way our hosts made us feel so comfortable, well, we just truly hated to leave. Thank you Jimmy and John for an amazing, (too brief), stay at your BnB!!!
Our stay was AMAZING! Jimmy and John are the perfect hosts. The fresh fruit and baked items, the beautiful grounds, the private fire pit, the comfortable apartment, the perfect location, and the way our hosts made us feel so comfortable, well, we just truly hated to leave. Thank you Jimmy and John for an amazing, (too brief), stay at your BnB!!!
10
Paul
Jul 7, 2024
·
Stayed 2 nights
We had a great time! This is a new B&B and they aim to please. Jimmy made sure we were comfortable and felt welcome …. There were plenty of snacks and fruit and beverages available. The rooms were cozy and well-decorated. Bravo! We will come again!
We had a great time! This is a new B&B and they aim to please. Jimmy made sure we were comfortable and felt welcome …. There were plenty of snacks and fruit and beverages available. The rooms were cozy and well-decorated. Bravo! We will come again!
10
Cathy
Oct 13, 2024
·
Stayed 3 nights
The location was great. Although not a bed and breakfast, the host offers lots of home-baked goodies (muffins,cookies breads, etc. we enjoyed our stay and felt we were very well taken care of.
The location was great. Although not a bed and breakfast, the host offers lots of home-baked goodies (muffins,cookies breads, etc. we enjoyed our stay and felt we were very well taken care of.
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AI-generated summary based on recent guest reviews
10
David
Sep 1, 2026
·
Stayed 1 night
Modern place well located in pretty town of Woodstock. Very "self serve" in terms of check-in, food, etc. but also quite convenient that way. We enjoyed our stay!
Modern place well located in pretty town of Woodstock. Very "self serve" in terms of check-in, food, etc. but also quite convenient that way. We enjoyed our stay!
10
Donald
Jul 29, 2026
·
Stayed 2 nights
The room and amenities exceeded our expectations. It was the best B & B we ever stayed in. The location was near shopping, restaurants and hiking trails. I highly recommend. You will not be disappointed.
The room and amenities exceeded our expectations. It was the best B & B we ever stayed in. The location was near shopping, restaurants and hiking trails. I highly recommend. You will not be disappointed.
10
michael
Mar 16, 2026
·
Stayed 1 night
Very cool space- a lottle unorthodox, but so much the better!
Very cool space- a lottle unorthodox, but so much the better!
10
Meghan
Mar 3, 2026
·
Stayed 2 nights
We've stayed at Jimmy's a couple of times and have had great experiences both visits. Highly recommend if you're in the Woodstock area!
We've stayed at Jimmy's a couple of times and have had great experiences both visits. Highly recommend if you're in the Woodstock area!
10
Heather
Jan 23, 2026
·
Stayed 1 night
Wonderful amenities, location, and team, Highly recommend and would love to stay again
Wonderful amenities, location, and team, Highly recommend and would love to stay again
FAQs about Stay At Jimmy's
Is parking available at the property?
Free self parking is available on-site. It is an outdoor parking area, and no reservation is required.
What type of breakfast is offered?
A complimentary continental breakfast is served daily from 7:00 AM to 9:00 AM.
Does the property allow pets?
Pets are allowed at the property with a fee of USD 75 per accommodation, per stay. Service animals are exempt from fees.
What are the check-in and check-out times?
Check-in is from 3:00 PM until 11:30 PM, and check-out is by 11:00 AM. Early or late check-in/check-out may be available upon request, but additional charges may apply.
What accessibility features does the property offer?
The property features step-free entrances and wheelchair-accessible facilities, including public areas and bathrooms. Specific details on room accessibility should be confirmed with the property.
Where is the property located in relation to key landmarks?
The property is located within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care and Ottauquechee Health Center. It is approximately 15.4 miles from Killington Resort and 18.1 miles from Dartmouth College.
What are the policies for guests staying with children?
Children 18 years old and younger are not permitted at this property.
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Prices for upcoming dates
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- 2026-12-29: 585.1057921020508USD
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There is no front desk at this property. Guests planning to arrive outside of normal check-in hours will receive an email within 24 hours before arrival with special check-in instructions and an access code. The host will greet guests on arrival.Information provided by the property may be translated using automated translation tools.
Check-in must be done by someone who is at least 21 years old.
- Extra-person charges may apply and vary depending on property policy
- Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
- Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
- This property accepts credit cards and debit cards; cash is not accepted
- This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
- Children 18 years old and younger are not permitted at this property.
- Pet fee: USD 50 per accommodation, per stay (maximum USD 50 per stay)
- Service animals are exempt from fees
The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.
Popular amenities
Parking
Free Wi-Fi
Breakfast in the Room
Garden
Free Parking
Parking Onsite
Parking
Parking
Free Parking
Parking Onsite
Internet
Free Wi-Fi
General
Breakfast in the Room
Activities
Garden
Terrace