Name: Winchester Inn
Address: 35 South 2nd Street, Historic Downtown District, Ashland, Oregon, United States of America, Ashland, Jackson County, US
Price range: $165–$617 per night
Rating: 9.43

What guests think

Across many reviews, Winchester Inn is praised for its walkable downtown Ashland location, comfortable rooms, and standout complimentary breakfast and restaurant, with consistently friendly, professional service enhancing relaxing stays for theatergoers and leisure travelers.

Many note tasteful Victorian decor, quiet nights, and features like balconies or fireplaces that add comfort. Some guests report maintenance or noise issues—heating and plumbing quirks, stained carpets, a small TV, or difficulty reaching staff late. Ideal for a relaxed boutique B&B experience in Ashland.

Facilities

Cleanliness

Rooms

Service

Location

Dining

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AI-generated summary based on recent guest reviews

Facilities

On-site restaurant and bar are highly regarded, and several guests enjoy the gardens and outdoor seating.

Related guest reviews

10

Len

May 16, 2025

·

Stayed 2 nights

quaint room. Fantastic restaurant. Excellent staff. Grounds need some sttention.

10

Monica

Jan 14, 2025

·

Stayed 2 nights

Our stay was great the staff was helpful and on top of everything! Also they have a fabulous restaurant and bar. We enjoyed some evening drinks and if we wanted could take back the drinks to our room. The breakfast was heavenly and the waiter provided top notch service. The room was clean, neat and they proved lovely treats. All in all I will be back.

10

Nick

Jul 23, 2025

·

Stayed 1 night

This inn offers a relaxing and comfortable stay. The location is centrally located in the heart of Ashland and the accomodations are amazing. We loved the welcome cookies and the breakfast was incredible. The Victorian architecture of the Inn, the gardens, and surrounding cottages were beatiful. There were so many places to sit and enjoy the gardens, food, and drinks.

10

Robin

Oct 24, 2024

·

Stayed 1 night

Lovely hotel in downtown Ashland. High end restaurant attached with lovely bar, as well as outdoor seating options. Walkable to all things in downtown. Stairs required up to room. Large comfortable room. Very nice breakfast. Overall, hotel is expensive, but nice. We really enjoy the restaurant.

8

Sid

Jun 15, 2025

·

Stayed 2 nights

The 2 full bedrooms with 2 large bathrooms was very convenient. Basically the unit is a converted garage surrounded by parking lots which made it noisy. Location is centrally located and excellent.

10

carolyn

Dec 23, 2023

·

Stayed 1 night

Amazing room with a balcony, fire place, comfy bed and beautiful walk in shower. It was so nice having a beautiful restaurant down stairs.

10

Kathleen

Feb 21, 2025

·

Stayed 1 night

Comfortable rooms with many amenities. Their sister restaurant across the street, Chateaubriand, is amazing!!!

10

Gregory

Aug 8, 2024

·

Stayed 1 night

Beautiful, extremely well maintained property in the heart of Ashland with lots of character and deluxe amenities. Very friendly and helpful staff. Gourmet restaurant on premises and superb breakfast with many options. Walk to everything. Highly recommend.

10

Bette

Aug 27, 2025

·

Stayed 2 nights

Beautiful setting with great service and food. Only problem was the bees nest above our patio room. Couldn’t sit outside because of the bees.

10

Paula

Oct 2, 2023

·

Stayed 2 nights

This is such a fantastic place to stay in Ashland Oregon. The accommodations are lovely and the on-site restaurant is truly incredible.

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AI-generated summary based on recent guest reviews

Cleanliness

Rooms and common areas are generally described as very clean. One review reports stained or dirty carpets as an ongoing issue.

Related guest reviews

10

Jen

Aug 12, 2023

·

Stayed 2 nights

My husband and I had a wonderful weekend in Ashland at the Winchester Inn. Such a unique property and so quiet at night! We stayed in the Sunset room, which has a nice little balcony and great view. The bed was really comfortable and the room was tastefully decorated and very clean. Little touches like a personalized card welcoming us and treats in the room go a long way. Breakfast was amazing...2 course on their beautiful patio. I was very impressed and will definitely be back!

10

Enrique Emanuel

Nov 2, 2023

·

Stayed 1 night

Located very close to downtown Ashland. Comfortableand clean rooms. All instructions for guests are clearly provided in a series of messages throughout the room and bathroom. The staff is very friendly, and the breakfast is plentiful, varied, and delicious. Choose it if you would like to know the city on foot.

10

Dona

Sep 25, 2023

·

Stayed 1 night

Staff very nice. Professional. Bed and Breakfast very clean, comfortable and quiet. Little chocolates are not very good. Could change that feature to be a more pleasant, appealing .

10

Monica

Jan 14, 2025

·

Stayed 2 nights

Our stay was great the staff was helpful and on top of everything! Also they have a fabulous restaurant and bar. We enjoyed some evening drinks and if we wanted could take back the drinks to our room. The breakfast was heavenly and the waiter provided top notch service. The room was clean, neat and they proved lovely treats. All in all I will be back.

10

Rob

Nov 3, 2024

·

Stayed 1 night

Winchester Inn is great place to stay in Ashland. The rooms are spacious, well furnished, clean, and comfy. It is close to the theaters and downtown area so you don't have to drive anywhere once you check in. There are a number of breakfast options and the food is excellent. We would definitely stay there again!

10

william

Oct 4, 2023

·

Stayed 1 night

This is an excellent hotel. Large room, immaculate furnishings (room cookies too!) and excellent breakfast, plus it is perfectly located to stroll Ashland. Highly recommended.

10

Jody

Jun 22, 2024

·

Stayed 2 nights

The staff was courteous, helpful, and conversational. Rooms were clean and stylish.

10

Shanna

Sep 8, 2025

·

Stayed 2 nights

Beautiful property. The room was spacious and clean. The sheets were soft and the bed was comfortable. The wait staff was very professional and attentive. The breakfast was delicious and included in the stay. It was walkable to Old Town Ashland. We stayed on foot for most of our stay. Very close to Lithia Park, dining and entertainment. Highly recommend.

8

Rebecca A

Jan 3, 2025

·

Stayed 1 night

The place and staff is fabulous. Always like it. Sorry to say I have the same complaint now as last time we were there, and we stayed in a different room. The carpets were filthy. Even if they were clean, they looked horrible with all the stains. How about hard wood floors or..... Thanks for listening.

10

Baki

Oct 24, 2024

·

Stayed 1 night

Booked this last minute and was very pleased-very friendly staff, great clean room, very close to restaurants, and a wonderful complimentary real breakfast! I would definitely choose this place again.

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AI-generated summary based on recent guest reviews

Rooms

Rooms are often spacious, comfortable, and charmingly decorated, with features like balconies, fireplaces, or walk-in showers in some. A few guests mention issues such as heating/cooling and plumbing quirks, small TVs, bed comfort, or occasional noise.

Related guest reviews

10

Laura

Sep 16, 2025

·

Stayed 1 night

Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!

10

Jen

Aug 12, 2023

·

Stayed 2 nights

My husband and I had a wonderful weekend in Ashland at the Winchester Inn. Such a unique property and so quiet at night! We stayed in the Sunset room, which has a nice little balcony and great view. The bed was really comfortable and the room was tastefully decorated and very clean. Little touches like a personalized card welcoming us and treats in the room go a long way. Breakfast was amazing...2 course on their beautiful patio. I was very impressed and will definitely be back!

10

Heather

Jul 6, 2025

·

Stayed 1 night

The room was amazing, and perfect location . The only negative was how small the tv was but we didn’t end up using it do wasn’t a big deal. The fire place motor sounded like it was on when everything was turned off. The room was amazing and definitely will come back, breakfast was good only bummer was the expresso machine was broken. The bed was comfortable, and staff was great. I love the little touch and personalization in the room.

10

Christi

Aug 30, 2025

·

Stayed 2 nights

Such a unique Victorian place! So charming, clean and spacious….

8

Sid

Jun 15, 2025

·

Stayed 2 nights

The 2 full bedrooms with 2 large bathrooms was very convenient. Basically the unit is a converted garage surrounded by parking lots which made it noisy. Location is centrally located and excellent.

10

carolyn

Dec 23, 2023

·

Stayed 1 night

Amazing room with a balcony, fire place, comfy bed and beautiful walk in shower. It was so nice having a beautiful restaurant down stairs.

8

Frederick

Sep 27, 2023

·

Stayed 1 night

We were in the Catherine M room. There was nowhere to plug in the tea or coffee pot. The cords were too short to reach the plugs. The bed was difficult, as it humped up in the middle, and it caused us to feel as if we were falling out the sides. The hostess was very pleasant. Breakfast was good.

10

Dirk

Jul 2, 2025

·

Stayed 1 night

Beautiful property, really comfortable bed, pillows and sheets!

6

Robert

Sep 19, 2024

·

Stayed 5 nights

The heating/cooling are awful. Some maintenance needs to be done. Takes forever to get hot water. Sink drains are slow. The breakfasts are fantastic! Still, we won't be going back.

10

Shanna

Sep 8, 2025

·

Stayed 2 nights

Beautiful property. The room was spacious and clean. The sheets were soft and the bed was comfortable. The wait staff was very professional and attentive. The breakfast was delicious and included in the stay. It was walkable to Old Town Ashland. We stayed on foot for most of our stay. Very close to Lithia Park, dining and entertainment. Highly recommend.

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AI-generated summary based on recent guest reviews

Service

Service is widely praised as friendly, professional, and helpful, with thoughtful touches and efficient check-in. One guest reported difficulty reaching staff late in the evening.

Related guest reviews

10

Laura

Sep 16, 2025

·

Stayed 1 night

Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!

10

Linda

May 27, 2023

·

Stayed 1 night

The reception staff were very welcoming, friendly and helpful.

10

Debra

Jul 29, 2023

·

Stayed 1 night

Beautiful property in downtown Ashland. Walkable to the theater restaurants shops. The staff was very friendly and welcoming. They called me to let me know early check-in was available.

10

Monica

Jan 14, 2025

·

Stayed 2 nights

Our stay was great the staff was helpful and on top of everything! Also they have a fabulous restaurant and bar. We enjoyed some evening drinks and if we wanted could take back the drinks to our room. The breakfast was heavenly and the waiter provided top notch service. The room was clean, neat and they proved lovely treats. All in all I will be back.

4

Karen

May 14, 2024

·

Stayed 1 night

I booked the Garden Room for a Queen bed and a sofa bed. I even asked again when I was shown the room if the sofa made into a bed and ahead of time asked to be sure there would be extra bedding for the sofa bed. I was assured upon check in that the sofa made into a bed. It does not. The Queen is more of a double than a Queen and the other guest had to sleep in the bay window minus extra bedding. I tried to get help by calling front desk, no answer. The dishwasher offered his condolences, the staff are nice, but this is poor service to not be able to reach anyone for help in the evening. Very disappointed.

10

Larry

Jul 2, 2024

·

Stayed 1 night

Staff was excellent! Room is beautiful! Well stocked! Easy access to restaurants!

10

Christine

Jul 29, 2024

·

Stayed 3 nights

Incredibly friendly and helpful staff. Gorgeous accommodations and oh so quiet and peaceful. Amazing breakfast! Highly recommend.

10

Kevin

Jun 25, 2024

·

Stayed 1 night

Absolutely wonderful property and outstanding service.

10

Jody

Jun 22, 2024

·

Stayed 2 nights

The staff was courteous, helpful, and conversational. Rooms were clean and stylish.

10

Shanna

Sep 8, 2025

·

Stayed 2 nights

Beautiful property. The room was spacious and clean. The sheets were soft and the bed was comfortable. The wait staff was very professional and attentive. The breakfast was delicious and included in the stay. It was walkable to Old Town Ashland. We stayed on foot for most of our stay. Very close to Lithia Park, dining and entertainment. Highly recommend.

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AI-generated summary based on recent guest reviews

Location

Excellent central location within easy walking distance of downtown, restaurants, theaters, and Lithia Park. Ideal for Oregon Shakespeare Festival visits.

Related guest reviews

10

Laura

Sep 16, 2025

·

Stayed 1 night

Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!

10

Enrique Emanuel

Nov 2, 2023

·

Stayed 1 night

Located very close to downtown Ashland. Comfortableand clean rooms. All instructions for guests are clearly provided in a series of messages throughout the room and bathroom. The staff is very friendly, and the breakfast is plentiful, varied, and delicious. Choose it if you would like to know the city on foot.

10

Debra

Jul 29, 2023

·

Stayed 1 night

Beautiful property in downtown Ashland. Walkable to the theater restaurants shops. The staff was very friendly and welcoming. They called me to let me know early check-in was available.

10

Nick

Jul 23, 2025

·

Stayed 1 night

This inn offers a relaxing and comfortable stay. The location is centrally located in the heart of Ashland and the accomodations are amazing. We loved the welcome cookies and the breakfast was incredible. The Victorian architecture of the Inn, the gardens, and surrounding cottages were beatiful. There were so many places to sit and enjoy the gardens, food, and drinks.

10

Robin

Oct 24, 2024

·

Stayed 1 night

Lovely hotel in downtown Ashland. High end restaurant attached with lovely bar, as well as outdoor seating options. Walkable to all things in downtown. Stairs required up to room. Large comfortable room. Very nice breakfast. Overall, hotel is expensive, but nice. We really enjoy the restaurant.

8

Sid

Jun 15, 2025

·

Stayed 2 nights

The 2 full bedrooms with 2 large bathrooms was very convenient. Basically the unit is a converted garage surrounded by parking lots which made it noisy. Location is centrally located and excellent.

10

Rob

Nov 3, 2024

·

Stayed 1 night

Winchester Inn is great place to stay in Ashland. The rooms are spacious, well furnished, clean, and comfy. It is close to the theaters and downtown area so you don't have to drive anywhere once you check in. There are a number of breakfast options and the food is excellent. We would definitely stay there again!

10

Becky

Aug 13, 2023

·

Stayed 1 night

I was attending a show at the Oregon Shakespeare Festival with my husband and we only stayed one night. Its a 2 min walk to the venue. We were in the heart of downtown, close to restaurants and shops. Our room was pleasantly comfortable, bathroom is spacious and well stocked. The complimentary breakfast was fantastic. We would definitely recommend to our friends and stay here again the next time we pass through.

10

Shanna

Sep 8, 2025

·

Stayed 2 nights

Beautiful property. The room was spacious and clean. The sheets were soft and the bed was comfortable. The wait staff was very professional and attentive. The breakfast was delicious and included in the stay. It was walkable to Old Town Ashland. We stayed on foot for most of our stay. Very close to Lithia Park, dining and entertainment. Highly recommend.

10

Baki

Oct 24, 2024

·

Stayed 1 night

Booked this last minute and was very pleased-very friendly staff, great clean room, very close to restaurants, and a wonderful complimentary real breakfast! I would definitely choose this place again.

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AI-generated summary based on recent guest reviews

Dining

Breakfast is consistently highlighted as excellent and included, with variety and gluten-free options. The on-site restaurant and bar, and a sister venue across the street, are frequently praised.

Related guest reviews

10

Ellen

Dec 22, 2023

·

Stayed 1 night

Breakfast was amazing!

10

Leonilda

Jan 17, 2025

·

Stayed 1 night

Great beautiful Inn with unique rooms. Delicious breakfast nenu with gluten-free items that are wonderful and I so enjoy

10

Monica

Jan 14, 2025

·

Stayed 2 nights

Our stay was great the staff was helpful and on top of everything! Also they have a fabulous restaurant and bar. We enjoyed some evening drinks and if we wanted could take back the drinks to our room. The breakfast was heavenly and the waiter provided top notch service. The room was clean, neat and they proved lovely treats. All in all I will be back.

10

Nick

Jul 23, 2025

·

Stayed 1 night

This inn offers a relaxing and comfortable stay. The location is centrally located in the heart of Ashland and the accomodations are amazing. We loved the welcome cookies and the breakfast was incredible. The Victorian architecture of the Inn, the gardens, and surrounding cottages were beatiful. There were so many places to sit and enjoy the gardens, food, and drinks.

10

Robin

Oct 24, 2024

·

Stayed 1 night

Lovely hotel in downtown Ashland. High end restaurant attached with lovely bar, as well as outdoor seating options. Walkable to all things in downtown. Stairs required up to room. Large comfortable room. Very nice breakfast. Overall, hotel is expensive, but nice. We really enjoy the restaurant.

10

Rob

Nov 3, 2024

·

Stayed 1 night

Winchester Inn is great place to stay in Ashland. The rooms are spacious, well furnished, clean, and comfy. It is close to the theaters and downtown area so you don't have to drive anywhere once you check in. There are a number of breakfast options and the food is excellent. We would definitely stay there again!

10

Gregory

Aug 8, 2024

·

Stayed 1 night

Beautiful, extremely well maintained property in the heart of Ashland with lots of character and deluxe amenities. Very friendly and helpful staff. Gourmet restaurant on premises and superb breakfast with many options. Walk to everything. Highly recommend.

10

Shanna

Sep 8, 2025

·

Stayed 2 nights

Beautiful property. The room was spacious and clean. The sheets were soft and the bed was comfortable. The wait staff was very professional and attentive. The breakfast was delicious and included in the stay. It was walkable to Old Town Ashland. We stayed on foot for most of our stay. Very close to Lithia Park, dining and entertainment. Highly recommend.

10

Baki

Oct 24, 2024

·

Stayed 1 night

Booked this last minute and was very pleased-very friendly staff, great clean room, very close to restaurants, and a wonderful complimentary real breakfast! I would definitely choose this place again.

10

Paula

Oct 2, 2023

·

Stayed 2 nights

This is such a fantastic place to stay in Ashland Oregon. The accommodations are lovely and the on-site restaurant is truly incredible.

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AI-generated summary based on recent guest reviews

Su	Mo	Tu	We	Th	Fr	Sa
				1 $597	2 $512	3 $398
4 $283	5	6	7	8 $498	9	10 $617
11 $300	12 $255	13 $568	14 $589	15 $579	16 $368	17 $353
18 $313	19 $303	20 $322	21 $322	22 $326	23 $347	24 $351
25 $303	26 $185	27 $172	28 $176	29 $165	30 $202	31 $201

Su	Mo	Tu	We	Th	Fr	Sa
		1	2	3	4	5
6	7	8	9	10	11	12
13	14	15	16 $464	17	18	19
20 $188	21 $271	22 $477	23	24	25	26
27 $245	28 $268	29 $277	30 $301

Select dates to see prices and availability

About this property

Location

Room options

Suite, 1 Queen Bed with Sofa Bed (Courtyard)

Superior Suite, Mountain View

Suite, 1 Bedroom (Silverdale)

Double Room, 1 King Bed (Andrew G)

Suite, 1 King Bed (Barbara Howard)

Double Room, 1 Queen Bed (Catharine M)

Suite, 2 Bedrooms (Duet Suite)

Suite, 1 Queen Bed with Sofa Bed (Brighton)

Double Room, 1 King Bed (Enders)

Double Room, 1 Queen Bed (Patio)

Double Room, 1 King Bed (Peter Benjamin)

Double Room, 1 Queen Bed (Marjorie Roy)

Double Room, 1 Bedroom (Sylvan)

Double Room, 1 King Bed (Sunset)

Family Suite, City View

Suite, Garden View

Double Room, 1 Bedroom (Garden)

Double Room, 1 King Bed (Eastlake)

Suite, 1 King Bed (Fordyce)

Double Room (Queen Anne)

Suite, 1 King Bed with Sofa Bed (Robert Gordon)

Suite, 1 King Bed (Hargadine)

Suite, 1 King Bed (Eleanor Rose)

Guest reviews

Superb

Who stays here?

What guests think

Property Policies

Check-in instructions

Good to know

Optional extras

FAQs about Winchester Inn

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Prices for upcoming dates