Winchester Inn Ashland, Ashland ➤ Reviews, Rooms & Prices 2025

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About the Hotel

35 S. 2Nd St., Ashland, Oregon, United States of America, 97520

The Winchester Inn is a historic hotel in Ashland, Oregon, known for its acclaimed culinary offerings and personalized luxury. It features 21 uniquely designed rooms and suites, tiered English gardens, and a celebrated restaurant, Alchemy. Located near the Oregon Shakespeare Festival and downtown amenities, the inn is a significant landmark in the region's cultural landscape.

Location

Centrally located in Ashland, the Winchester Inn is within walking distance of the Oregon Shakespeare Festival and various art galleries, shops, and restaurants. The inn is approximately 18.5 miles from Rogue Valley International-Medford Airport, ensuring convenient access for travelers exploring Southern Oregon.

Rooms

Each guestroom at Winchester Inn provides premium amenities, including flat-screen TVs, honor bars, and luxurious bedding. Suites are spacious, offering additional comforts like soaking tubs and romantic fireplaces. All accommodations come with private bathrooms, featuring Egyptian cotton towels and gourmet breakfast for two. Cottages offer a unique option for families seeking shared space with privacy.

Eat & Drink

Alchemy Restaurant and Bar, located on-site, is renowned for its seasonal, locally sourced menu and award-winning wine list recognized by Wine Spectator. The restaurant offers a diverse range of cocktails and a well-curated bourbon selection. Additionally, guests can enjoy a two-course gourmet breakfast and afternoon pastry treats during their stay.

Leisure & Business

The Winchester Inn features beautiful gardens with small sitting areas for relaxation. It provides spaces suitable for events, meetings, and intimate gatherings, all backed by attentive service. Guests can also take advantage of complimentary Wi-Fi, valet service, and room service.

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Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals

King Room

Max:

2 persons

39 m²

Bed options:

1 King Size Bed

Garden view

Shower

Coffee machine

room details

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King Suite

Max:

2 persons

42 m²

Bed options:

1 King Size Bed

City view

Shower

Coffee machine

room details

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Family Room

Max:

2 persons

33 m²

Bed options:

1 King Size Bed

Garden view

Shower

Coffee machine

room details

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Price and Room Availability Calendar

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Getting around

A list of all available modes of transport

City Center

Ashland1000 ft

Airports

Rogue Valley International-Medford (MFR) 16.0 mi

Klamath Falls (LMT) 65.4 mi

Bus

Bus stop700 ft

Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

Delicious Breakfast!

“The breakfast was a standout feature, with a great variety of high-quality food served in a lovely atmosphere.” view full review

Comfortable Rooms!

“The rooms were incredibly comfortable, with amazing bedding and all the little extras like a stocked fridge that made our stay special.” view full review

Luxury Showers!

“The showers were a perfect blend of luxury and functionality, complete with plush bathrobes that added to the relaxing experience.” view full review

Tasty Treats!

“The complimentary snacks, especially the gluten-free cookies, were a good bonus that made our stay even sweeter!” view full review

General

No smoking on site
Wi-Fi
Parking
Concierge desk
No pets allowed
Rooms/ Facilities for disabled
Baggage storage
Allergy-free rooms
Smoke detectors
Fire extinguishers
Key access

Sports & Fitness

Hiking
Tennis court
Golf course

Guest Parking

Electric kettle

Services

Housekeeping
Dry cleaning
Welcome drink
Happy hour

Dining

Restaurant
Bar/ Lounge area
Dinner
Special diet menus

Business

Meeting/ Banquet facilities
Fax/Photocopying

Children

Cribs

Spa & Leisure

Garden area

Room features

Air conditioning
Heating
Mini-bar
Sitting area
Patio
Garden furniture
Tea and coffee facilities
Ironing facilities

Bathroom

Free toiletries

Self-catering

Electric kettle

Media

Flat-screen TV
AM/FM alarm clock

Room decor

Carpeted floor

Location

35 S. 2Nd St., Ashland, Oregon, United States of America, 97520

Map view

35 S. 2Nd St., Ashland, Oregon, United States of America, 97520

City landmarks

Parks

Lithia Park

2100 ft

Museums

ScienceWorks Hands-On Museum

1.4 mi

322 N Pioneer St

Gathering Glass Studio

2200 ft

Museums

Schneider Museum of Art

1.2 mi

Parks

North Mountain Park

1.3 mi

Railroad Park

3600 ft

247 Oak St

Oakleaf Studio

2200 ft

Gallery

Ashland Art Works

2400 ft

E Main St & Garfield St

Garfield Park

4900 ft

27 E Hersey St

Ashland Creek Park

3600 ft

215 4th St

Illahe Studios and Gallery

3700 ft

Ashland Creek

4700 ft

The Siskiyou

1.0 mi

Ashland Dog Park

1.3 mi

183 Hitt Rd

Acid Castle Boulders Access Point

1.2 mi

620 N Mountain Ave

North Mountain Park Nature Center

1.3 mi

190 Skycrest Dr

Hald/ Strawberry Park

1.4 mi

1699 Homes Ave

Hunter Park

1.5 mi

Store

Deja Vu

1.5 mi

Nearby

Broadway Theatre

Oregon Shakespeare Festival

1300 ft

Libraries

Ashland Library

900 ft

Libraries

Ashland

1000 ft

111 E Main St

Zagorska Oasis

1200 ft

Store

Ashland Food Co-op

1800 ft

Parks

Bluebird Park

1900 ft

264 E Main St

Prize

500 ft

Gallery

Ashland Art Center

600 ft

N Main St

Lithia Fountains

1600 ft

Store

Northwest Nature Shop

1800 ft

N Main St

Downtown Plaza

1800 ft

Restaurants

Alchemy Restaurant and Bar

100 ft

35 S 2nd St at the Winchester Inn

Smithfields Restaurant and Bar

200 ft

36 South 2nd Street

Paddy Brannans Irish Pub

200 ft

23 S 2nd St

Pangea

400 ft

272 E Main St

Hearsay Restaurant

400 ft

40 S 1st St

Cafe Aroma & AromaDome Wellness Center

300 ft

296 E Main St

Pie + Vine

500 ft

358 East Main Street

Redzone Sports Bar N Grill

400 ft

303 E Main St

The Village Baker of Ashland

600 ft

372 E Main St

Reviews and Ratings

Feedback from previous guests about their experience.

88%

liked the hotel and would stay again

Charming location

Outstanding dining

Small rooms

High price

8.8/10

Great

Rooms

8.3

Location

9.3

Service

9.0

Dining

9.0

Alex

United States of America, February 2024

9.0/10

My stay at the hotel was absolutely delightful! The rooms were both comfortable and luxurious, with an extra special turn-down service that made me feel truly pampered. The beds were incredibly cozy, and the bathrooms were pristine. However, some rooms vary in size from small and cozy to more roomy suites with a separate sitting area which can impact the overall experience.

Rooms

9.0

I loved the comfortable beds and nice bathrooms in the rooms. They truly made my stay special.

Service

9.0

The service at the hotel was beyond excellent. The staff was always there to help and share their local knowledge, making my stay feel personalized and enjoyable.

Location

9.0

The location of the hotel was perfect for me, right in town and with easy access to the Shakespeare Festival plays. I also appreciated having a private entrance, adding a touch of exclusivity to my stay.

Dining

9.0

The dining experience at the hotel was exceptional, exceeding my expectations. The breakfast was above and beyond what you typically find at a B&B, and the grilled Teppanyaki fish was a standout dish.

Facilities

9.0

The facilities at the hotel were top-notch, providing everything I needed for a comfortable stay. However, keep in mind that prices may reflect the luxurious experience offered.

Ralph

United States of America, October 2023

9.2/10

My stay at the hotel was truly enjoyable. The rooms were lovely and stylish, with thoughtful touches, although it was a bit cold. The service was terrific and very attentive, and I could get tickets to the Shakespeare Festival at nearly half price by calling in advance. The location was perfect, right in town, allowing easy access to theaters and excellent restaurants. The dining experience was really good with excellent service, coming in a close second, and the facilities were top-notch. However, the glasses were crystal cut, which was a bit of a concern.

Rooms

8.0

The room was large and well-appointed, with a private balcony.

Service

9.0

The service was great and very attentive. I appreciated being able to get tickets to the Shakespeare Festival at a discount.

Location

10.0

The location was ideal, right in town, making it easy to walk to theaters and excellent restaurants.

Dining

9.0

The dining was really good with excellent service, definitely better than most places I've been.

Facilities

10.0

The facilities were excellent, offering everything I needed during my stay.

Jeffrey

United States of America, April 2023

8.6/10

I had a wonderful stay at this hotel. The rooms were cozy and had a small deck overlooking a charming garden area. The service was exceptional, with friendly and helpful staff. The location was perfect, close to all that Ashland has to offer. The dining experience was outstanding, with delicious food and thoughtful touches. Overall, a great value for the money.

Rooms

8.0

The rooms felt cozy and had a small deck attached, offering a lovely view of the garden.

Service

9.0

The staff was friendly, personable, and attentive from start to finish.

Location

9.0

The hotel is a hidden gem right off the main road, close to everything Ashland has to offer.

Dining

9.0

The dining experience was outstanding with the best B&B breakfast I've ever had.