Winchester Inn, Ashland ➤ Reviews, Rooms & Prices 2025

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About the Hotel

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

The Winchester Inn, a 5-star hotel, offers luxury and comfort with convenient access to art galleries and the Oregon Shakespeare Festival. This acclaimed Ashland hotel features fine dining at Alchemy Restaurant and Bar, award-winning for its wine and cocktail program.

Rooms & Amenities

Winchester Inn provides a range of lodging options, including luxurious rooms, suites, and cottages. Every accommodation features amenities such as flat-screen TVs, Antica Farmacista toiletries, and gourmet breakfast for two.

Dining & Options

Dining includes the celebrated Alchemy Restaurant, recognized for its innovative cuisine using seasonal ingredients, and a sophisticated wine list. Guests can also enjoy afternoon pastry treats delivered to their rooms.

Leisure & Activities

Guests can relax in the award-winning gardens featuring small sitting areas, perfect for reading or enjoying a glass of wine. The Winchester Inn is also a short distance from the Oregon Shakespeare Festival and local wineries, offering various cultural experiences.

Services & Business

The Winchester Inn provides attentive service, including valet parking, laundry service, and morning coffee. For business events, the hotel offers meeting facilities that can accommodate up to 30 participants.

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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

Comfort Triple Room Shower

Max:

2 persons

33 m²

Bed options:

1 King-size bed

Garden view

Shower

Coffee machine

room details

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Double Room Garden View

Max:

2 persons

33 m²

Bed options:

1 King-size bed

Garden view

Shower

Coffee machine

room details

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Standard Queen Room

Max:

2 persons

28 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 Centre

Ashland300 m

Airports

Rogue Valley International-Medford (MFR) 25.7 km

Klamath Falls (LMT) 105.2 km

Bus

Bus stop200 m

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
Free parking
Off-site car park
Concierge desk
No pets allowed
Rooms/ Facilities for disabled
Luggage 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

Cots

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, 97520

Map view

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

City landmarks

Park

Lithia Park

620 m

Museum

ScienceWorks Hands-On Museum

2.2 km

322 N Pioneer St

Gathering Glass Studio

670 m

Museum

Schneider Museum of Art

1.9 km

Park

North Mountain Park

2.1 km

Railroad Park

1.1 km

247 Oak St

Oakleaf Studio

660 m

Gallery

Ashland Art Works

710 m

E Main St & Garfield St

Garfield Park

1.5 km

27 E Hersey St

Ashland Creek Park

1.1 km

215 4th St

Illahe Studios and Gallery

1.1 km

Ashland Creek

1.4 km

The Siskiyou

1.6 km

Ashland Dog Park

2.0 km

183 Hitt Rd

Acid Castle Boulders Access Point

2.0 km

620 N Mountain Ave

North Mountain Park Nature Center

2.1 km

190 Skycrest Dr

Hald/ Strawberry Park

2.2 km

1699 Homes Ave

Hunter Park

2.4 km

Store

Deja Vu

2.4 km

Nearby

Theatre

Oregon Shakespeare Festival

390 m

Library

Ashland Library

250 m

Library

Ashland

300 m

111 E Main St

Zagorska Oasis

340 m

Store

Ashland Food Co-op

530 m

Park

Bluebird Park

550 m

264 E Main St

Prize

140 m

Gallery

Ashland Art Center

170 m

N Main St

Lithia Fountains

470 m

Store

Northwest Nature Shop

520 m

N Main St

Downtown Plaza

540 m

Restaurants

Alchemy Restaurant and Bar

10 m

35 S 2nd St at the Winchester Inn

Smithfields Restaurant and Bar

50 m

36 South 2nd Street

Paddy Brannans Irish Pub

50 m

23 S 2nd St

Pangea

110 m

272 E Main St

Hearsay Restaurant

120 m

40 S 1st St

Cafe Aroma & AromaDome Wellness Center

90 m

296 E Main St

Pie + Vine

130 m

358 East Main Street

Redzone Sports Bar N Grill

100 m

303 E Main St

The Village Baker of Ashland

160 m

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, 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, 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, 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.