390 reviews
From
$29335 South 2nd Street, Ashland, 97520, Oregon, United States
390 reviews
1/147
Restaurant
Free Private Parking
Free wifi
Spa tub
Air conditioning
Tennis court
Bar
Private entrance
Welcome to the stunning Winchester Inn, a 5-star gem nestled in the charming town of Ashland, Oregon! Just a stone's throw away from the city center—only 0.1mi away—you'll find yourself perfectly placed to explore all the delightful shops, theaters, and outdoor adventures that this vibrant locale has to offer. With room rates starting at just $293, you can indulge in luxury without breaking the bank!
As you step through the private entrance of this exquisite hotel, prepare to be dazzled by its array of amenities. Savor a complimentary breakfast each morning, followed by a day of relaxation in the spa tub or a friendly match on the free tennis court! If you’re longing for more adventure, take advantage of nearby golf courses (for an extra charge), or unwind with a refreshing drink at the bar while enjoying breathtaking mountain and garden views from your private balcony or patio. The beautifully designed rooms offer air conditioning, extra-long beds, and indulgent free toiletries to ensure your stay is nothing short of fabulous.
But don’t just take our word for it—join the 390 happy guests who have raved about their experiences at Winchester Inn! With features like free WiFi, private parking, and a picturesque garden, it’s no wonder this place is a favorite among travelers. Ready for your next unforgettable getaway? Book your escape to Winchester Inn and discover the enchanting beauty of Ashland!
Dining at the Winchester Inn is an experience that will tantalize your taste buds! Indulge in delectable morsels at the elegant Alchemy Restaurant and Bar, where modern and romantic vibes set the stage for an unforgettable meal. Their menu boasts an enticing array of American and French dishes, highlighting local ingredients that reflect the rich culture of Ashland. If you're looking for a family-friendly option, head over to Chateaubriand 36, a delightful steakhouse serving up classic French cuisine that’s perfect for all ages. With their warm atmosphere and exceptional service, every meal here promises to be as enchanting as the surroundings.
After a day filled with the enchanting sights of Ashland, return to the comfort of the Winchester Inn to unwind. Whether you're lounging in the spa tub, challenging a friend to tennis, or simply sipping a refreshing drink in the picturesque garden, relaxation is always just around the corner. With breathtaking mountain and garden views from many private balconies or patios, you can savor each moment as you soak in the beauty that surrounds you. The hotel is a haven for those who wish to escape the ordinary and dive into a world of serenity.
Of course, your stay wouldn’t be complete without indulging in some local exploration! Ashland is teeming with charm and excitement, so be sure to venture out and discover the nearby theaters, shops, and parks that have made this town famous. With room types catering to couples and families alike, and a range from cozy suites to spacious accommodations, the Winchester Inn is the perfect base for all your adventures. So pack your bags, and get ready for a getaway filled with luxury, leisure, and laughter at the enchanting Winchester Inn!
Closest airports
Rogue Valley International - Medford Airport
14.6miGrants Pass Airport
40.9miKlamath Falls Airport
49.7miRestaurant
Free Private Parking
Free wifi
Spa tub
Air conditioning
Tennis court
Bar
Private entrance
Parking On Site
Terrace
Mountain view
Non-smoking rooms
Patio
Garden view
Garden
View
Extra long beds (> 6.5 ft)
Free toiletries
Balcony
Bathtub
Show 6 photos
Studio, Queen Size
1 Sofa Bed
1 Queen Size Bed
400 sqft
Spa tub
Garden view
Private Bathroom
Bathtub
+
More details
Indulge in our Queen Studio Suite, a spacious 398 sqft oasis with a queen size bed and a comfortable sofa bed, offering a garden view and featuring a private bathroom with a spa tub. Enjoy modern amenities such as a flat-screen TV, minibar, and coffee machine in the air-conditioned comfort of this stylish suite.
Show 7 photos
Deluxe Suite
1 King Size Bed
1 Sofa Bed
495 sqft
Spa tub
Garden view
Private Bathroom
Bathtub
+
More details
Indulge in luxury and comfort in our Deluxe King Suite, a spacious 495 sqft suite with a King size bed, spa tub, and garden view. Enjoy the modern amenities and relax in the tranquil ambiance of this beautifully furnished suite.
Show 7 photos
Suite, Garden View
1 Queen Size Bed
1 Sofa Bed
400 sqft
Mountain view
Spa tub
Garden view
Private Bathroom
+
More details
Indulge in the luxury of our spacious Suite with Garden View, boasting 398 sqft of stylish comfort. Featuring a serene garden view, spa tub, and a plush Queen size bed, it's the perfect retreat for a relaxing couples' getaway.
Show 6 photos
King Room, Balcony
1 King Size Bed
420 sqft
Mountain view
Garden view
City view
Private Bathroom
+
More details
Indulge in the spacious comfort of our King Room with Balcony, featuring a stunning mountain, garden, or city view. Unwind and enjoy the privacy of your own bathroom, while savoring the convenience of in-room minibar, coffee machine, and flat-screen TV. The perfect retreat for couples seeking tranquility and luxury.
Show 5 photos
Deluxe Studio, King Size
1 King Size Bed
450 sqft
Mountain view
Spa tub
City view
Private Bathroom
+
More details
Indulge in the spacious elegance of our Deluxe King Studio Suite, offering stunning mountain and city views, a private spa tub, and a cozy fireplace. Relax in the comfort of the extra-long King size bed, and enjoy the convenience of amenities like a flat-screen TV, minibar, and coffee machine.
Show 5 photos
King Room
1 King Size Bed
355 sqft
Garden view
Private Bathroom
Private entrance
Minibar
+
More details
Experience ultimate comfort and luxury in our spacious King Room, featuring a private entrance, a garden view, and a relaxing bathtub. Unwind and indulge with amenities such as a minibar, a coffee machine, a flat-screen TV, and a private patio. Perfect for couples seeking a tranquil retreat.
Show 5 photos
Suite, Queen Size
1 Queen Size Bed
1 Sofa Bed
400 sqft
Mountain view
City view
Private Bathroom
Bathtub
+
More details
Experience ultimate comfort and luxury in our Queen Suite, boasting a spacious 398 sqft area with stunning mountain and city views. Pamper yourself in the private bathroom with a relaxing bathtub or unwind in the comfortable seating area. Enjoy modern amenities like a flat-screen TV, minibar, coffee machine, and more for a truly unforgettable stay.
Show 5 photos
Room With Garden View
1 Queen Size Bed
355 sqft
Garden view
Private Bathroom
Minibar
Coffee machine
+
More details
"Escape to our Double Room with Garden View and immerse yourself in tranquility as you enjoy the lush greenery from the comfort of your private oasis. This spacious, 355 sqft room is perfect for a romantic retreat, featuring a queen size bed, air conditioning, and a host of modern amenities to make your stay unforgettable." (213 symbols)
Show 4 photos
Queen Room
1 Sofa Bed
1 Queen Size Bed
355 sqft
Garden view
City view
Private Bathroom
Minibar
+
More details
Experience ultimate comfort in our Queen Room, featuring a spacious 355 sqft of indulgence. Enjoy stunning garden and city views, a private bathroom, a flat-screen TV, and luxurious amenities including a minibar and coffee machine. With a cozy sofa bed and a queen size bed, this room is perfect for 2 adults seeking a relaxing getaway.
Show 4 photos
Suite, King Size
1 Sofa Bed
1 King Size Bed
450 sqft
City view
Private Bathroom
Private entrance
Minibar
+
More details
Indulge in luxury with our spacious and stylish King Suite. This 452 sqft suite features a king-size bed, a spa tub, garden views, and a private bathroom with a bathtub. Enjoy a minibar, coffee machine, and flat-screen TV, while staying cool with air conditioning.
Show 4 photos
Family
1 King Size Bed
1 Sofa Bed
355 sqft
Mountain view
Garden view
City view
Private Bathroom
+
More details
Indulge in the spacious 355 sqft Family Room, featuring a king size bed and sofa bed. Enjoy stunning views of the mountains, garden, and city from your private balcony, along with amenities such as a bathtub, minibar, and flat-screen TV to ensure a comfortable and relaxing stay.
Show 11 photos
Suite, 2 Bedroom
1 Queen Size Bed
1 Sofa Bed
1 King Size Bed
905 sqft
City view
Private Bathroom
Private entrance
Microwave
+
More details
9.4
390 reviewsCategories of assessments
Cleanliness
Comfort
Location
Facilities
Staff
Value for money
WiFi quality
Breakfast
Featured reviews:
Catherine
9.1
January 2025
(See google reviews for pictures with this review) Queen Anne room is lovely. Comfy king bed and a twin. Tall windows facing north. Coffee maker and tea kettle and good size mini fridge. Fabulous breakfast and accommodating of dietary preferences or needs. Wonderful staff. Highly recommended. Rooms: 4 Service: 5 Location: 5 Nearby activities In addition to the theatres and restaurants nearby, the Ashland YMCA is a 15 minute drive. Good for a workout or a swim. Food & drinks Excellent breakfast included in Alchemy restaurant in the main building, and excellent French steakhouse across the street (Chateaubriand). Hotel highlights Luxury, Romantic
The only drawback to this room is the noisy AC/heat unit on the wall. Even on low. A quiet heat pump that allows for the fan to stay on (instead of cycling on & off) would be appreciated here :-)
Richard
10
August 2024
Great place and very well run. Staff are engaged, friendly, and helpful. Our king room was spacious and very good value for early week stays (when OSF is not scheduled). Breakfast was very nice. Delicious coffee and food. Ashland is very pleasant to walk, and we explored up the hills, historic district, and Lithia Park on foot. Roku and mini fridge in room was appreciated. AC was excellent despite mini heat wave. Morning and evening visits from the deer in the garden were nice.
Minor quibbles. Bed had topper that made it a bit too soft for our liking, so maybe an option to remove it? We booked 8am breakfast first day of two(earliest available) and assumed it would carry to second morning when we needed to leave promptly for long drive North, but ended up slightly later after missing call in afternoon to rebook and going down to desk a few hours later. Suggest they ask at check in all your breakfast times.
Sandi
10
September 2024
We loved our stay and are planning a return visit. The location is perfect for walking around Ashland. The park is an easy stroll down the road and you are a block off of E. Main Street where there is great shopping and restaurants. The breakfast at the Inn was exceptional. As wonderful as our room was, we were delighted by the fabulous fare served in the dining room of the main house. They had gluten free options that were delicious. We both rated the breakfast a 10/10. The restaurant was closed for dinner the night we stayed, but we will make certain we book our next stay on a night they are open. The grounds on the property are beautiful and well cared for. You can walk around them and there are places to sit and enjoy life.
Leslie
9.1
December 2024
Arrived in the dark to this charming property off season and was greeted by a very pleasant office staff who escorted us to our room. The room was very spacious, clean, and the bed and bedding was very comfortable. There were pleasant touches, like complimentary pastries in the room on arrival. The breakfast is indeed spectacular with two courses and a wide selection of entrees.
This is a charming, historic property and access to the units is on uneven surfaces. If you have mobility challenges, you should investigate whether you can access this property.
Judy
10
August 2024
Where to begin? This is most charmingly decorated in a traditional but not stuffy style. Everything is in good condition with modern touches like charging ports by the beds. It was all very comfortable and homey while also being very professional. Our stay included a breakfast which was generous and delicious. Service was friendly, helpful and yet not overly hovering. The gardens and yard were lovely and visited by fearless deer! The parking in the back had an unexpected electrical outlet to charge the car! I don’t know that I would stay anywhere else in Ashland!
There was nothing to dislike.
Nischal
8.2
January 2025
The staff (in particular Skye) was very friendly and accommodating. The room and bathroom was clean. Skye provided us with chocolates and comp'd the water due to the room and lack of breakfast inconveniences. Location is great with free parking available.
The room was advertised with breakfast included, however the restaurant was closed and no breakfast or a voucher was afforded to us. The bed and pillows were too soft and not supportive enough to sleep. The toilet had a slow drip leak that was annoying to sleep through.
Jacklin
9.1
July 2024
The property was beautiful and even though the parking spots were all filled, it did not feel crowded there. The balcony was comfortable and the cooling unit was set at a good temperature. The bed was AWESOME and the sofa bed was convenient and easy to set up. The bathroom was spacious and the products available were high quality, which went great with the fluffy towels. The breakfast was delicious, too, and we were within walking distance to the local restaurants and shops.
The coffee maker in my room did not work, but there was coffee and filters available had it worked.
Bernard
8.2
June 2024
The service by staff is outstanding. The property location cannot be beaten. The grounds are lovely. Breakfast is outstanding. The location is quiet yet near everything.
The room we received had a bathroom that was just adequate for my wife. My wife has mobility limits and needed two more bars for assistance in getting in and out of the shower/bath combo. For seniors a high comfort toilet would be most appreciated as the current one is too low. The sink needs attention as its drain plug and faucet handle need adjustments.
Lan
10
January 2025
I really enjoyed my time in Ashland. The city’s twinkling lights on rooftops during the winter nights create a warm and cozy atmosphere. Staying at the Winchester Inn for two days was a delightful surprise. The hotel has a charming, vintage European style, with beautifully detailed decor, and everything was spotless and well-maintained. I especially loved the windowsill in my room — it was the perfect spot to sit, read a book, or simply gaze out at the sparkling city lights…✨
Cora
10
September 2024
The breakfast potatoes are ridiculously good (get them!), and we liked everything we had over four mornings. Location is great for walking to Shakespeare, food, bookstore, and more. Love the hotel itself, and the grounds, beautiful and quiet. Perfect for hanging out as a couple and enjoying each other's company for our anniversary. Bed was super comfy, and the little afternoon treats are a cute touch.
Nothing! It was a wonderful stay. Nothing negative to say.
Attractions
Rogue River
14.2miAttractions
Rogue River
14.2miAirports
Rogue Valley International - Medford Airport
14.6miGrants Pass Airport
40.9miKlamath Falls Airport
49.7miAlchemy Restaurant and Bar
Cuisines
Ambiances
Chateaubriand 36
Cuisines
Ambiances
Restaurant
Free Private Parking
Free wifi
Spa tub
Air conditioning
Tennis court
Bar
Private entrance
Parking On Site
Terrace
Mountain view
Non-smoking rooms
Patio
Garden view
Garden
View
Extra long beds (> 6.5 ft)
Free toiletries
Balcony
Bathtub
Accessibility
Entire unit located on ground floor
Entire unit wheelchair accessible
Upper floors accessible by stairs only
Activities
Golf course
Happy hour
Hiking
Tennis court
Themed dinners
Bathroom
Additional bathroom
Bathrobe
Bathtub
Bathtub or shower
Free toiletries
Hairdryer
Private Bathroom
Shower
Spa tub
Toilet
Toilet paper
Towels
Bedroom
Alarm clock
Extra long beds (> 6.5 ft)
Linens
Wardrobe or closet
Business Facilities
Fax/Photocopying
Meeting/Banquet facilities
Cleaning Services
Daily housekeeping
Dry cleaning
Food & Drink
Bar
Minibar
Restaurant
Special diet meals (on request)
Tea/Coffee maker
Wine/Champagne
Food & drink safety
Breakfast to-go containers
Delivered food covered securely
Food can be delivered to guest accommodation
Front Desk Services
Baggage storage
Concierge
Invoice provided
General
Air conditioning
Carpeted
Facilities for disabled guests
Family rooms
Hardwood or parquet floors
Heating
Hypoallergenic room available
Non-smoking rooms
Private entrance
Smoke-free property
Internet
Free wifi
Kitchen
Coffee machine
Electric kettle
Microwave
Refrigerator
Living Area
Fireplace
Sitting area
Sofa
Media & Technology
Cable channels
Flat-screen TV
iPod dock
Radio
Telephone
TV
Video
Outdoors
Balcony
Garden
Outdoor furniture
Patio
Terrace
Parking
Free Private Parking
Parking On Site
Physical distancing
Cashless payment available
Room Amenities
Clothes rack
Fold-up bed
Iron
Socket near the bed
Sofa bed
Safety & security
Carbon monoxide detector
Fire extinguishers
Key access
Smoke alarms
Services
Wake-up service/Alarm clock
View
City view
Garden view
Inner courtyard view
Mountain view
View
From 16:00
Guests are required to show a photo identification and credit card upon check-in
Until 11:00
Pets are not allowed.
WiFi is available in all areas and is free of charge.
There's no age requirement for check-in
Come and go whenever you want
Free private parking is available on site (reservation is not needed).
Child policies
Children of all ages are welcome.
Children 9 and above will be charged as adults at this property.
To see correct prices and occupancy info, add the number and ages of children in your group to your search.
Crib and extra bed policies
0 - 2 years
3+ years
9+ years
Extra bed upon request
$45 per person per day
Additional fees are not calculated automatically in the total cost and will have to be paid for separately during your stay.
The maximum number of cribs, extra beds, and children allowed in existing beds can vary depending on the option booked.
All cribs and extra beds are subject to availability.
This property accepts cash only.
What's the check-in and check-out schedule at Winchester Inn?
When you book a stay at Winchester Inn, you can access your room from 04:00 PM and should leave by 11:00 AM.
Is there parking at Winchester Inn?
Yes, there is ample free private on-site parking available at the Winchester Inn. No reservation is required for parking.
How much does a stay at Winchester Inn cost?
At Winchester Inn, you can find rates starting from $293. It's important to consider that room type and booking dates can influence the final price. For clarity on rates, please input your dates.
What are the room types available at Winchester Inn?
The Winchester Inn offers a variety of room types including suites, doubles, and triples. The rooms range in size from 301 sqft to 904 sqft. Smoking is not allowed in any of the rooms. The occupancy for most rooms is 2 adults with no children, although some suites can accommodate up to 4 adults and 2 children. The bed sizes include Queen, King, and Twin beds.
Where can guests find entertainment in Winchester Inn?
Guests at the Winchester Inn have a variety of leisure amenities to enjoy. They can unwind and relax in the spa tub or play a round of golf on the hotel's golf course. For those who prefer to stay active, there is a tennis court available. Additionally, guests can take advantage of the hiking trails around the hotel or cozy up by the fireplace. The hotel also offers two on-site restaurants for guests to dine at.
Alchemy Restaurant and Bar provides a modern and romantic ambiance, and offers a range of cuisines including American, French, Local, and International. Chateaubriand 36, on the other hand, has a family-friendly atmosphere and specializes in French cuisine and steakhouse dishes. With these amenities, guests can have a relaxing stay and enjoy delicious meals during their time at the hotel.
Does Winchester Inn feature its own restaurants?
Yes, the Winchester Inn has two restaurants on site. The first one is Alchemy Restaurant and Bar, which offers a modern and romantic ambiance. They serve American, French, Local, and International cuisines. The second restaurant is Chateaubriand 36, known for its family-friendly atmosphere and French and Steakhouse cuisines.
Are both cash and credit cards valid payment options at Winchester Inn?
No, cash is not a valid payment option at Winchester Inn. However, they do accept American Express, Discover, Visa, and Mastercard as payment methods.
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