Name: Stay At Jimmy's
Address: 45 Pleasant Street, Woodstock, Vermont, United States of America, Woodstock, Vermont, United States of America
Rating: 10

Guest reviews

10

Exceptional

Based on 49 verified reviews

What guests think

AI-generated summary based on recent guest reviews

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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!

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.

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!

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.

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!

45 Pleasant Street, Woodstock, Vermont, United States of America

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 18.1 mi (29.1 km) from Dartmouth College and 15.4 mi (24.8 km) from Killington Resort.

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)

More location info

Property Policies

Check-in instructions

Everything you need to know for a smooth check-in.

Check-in

Check-out

From 15:00 to 23:30

Before 11:00

Good to know

Additional policies and info about this property.

Optional extras

Additional paid services you can request.

FAQs

Free self parking is available on-site. It is an outdoor parking area, and no reservation is required.

A complimentary continental breakfast is served daily from 7:00 AM to 9:00 AM.

Pets are allowed at the property with a fee of USD 75 per accommodation, per stay. Service animals are exempt from fees.

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.

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.

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.

Children 18 years old and younger are not permitted at this property.

Stay At Jimmy's

Amenities

Property description