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Winchester Inn
From
$20835 South 2nd Street, Ashland, OR 97520, US
Reservations:
+1-833-728-2041328 reviews
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1/147
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$208Call for great rates
+1-833-728-2041Pet Friendly
Free Private Parking
Free wifi
Spa tub
Air conditioning
Private entrance
Tennis court
Mountain view
Welcome to the Winchester Inn in beautiful Ashland, Oregon! This charming 5-star hotel is located just 0.1mi from the city center, making it the perfect place to stay while exploring all that Ashland has to offer. With 328 reviews and a minimum price starting at $208, the Winchester Inn is known for its exceptional service and comfortable accommodations.
The Winchester Inn offers a range of amenities to make your stay even more enjoyable. Wake up each morning to a delicious breakfast before heading out to explore the nearby golf course or take a hike in the stunning mountain view surroundings. After a long day of exploring, unwind in the spa tub or relax in the garden with a drink from the bar.
The hotel features a variety of room options to suit your needs, including pet-friendly and hypoallergenic rooms. Each room is equipped with free WiFi, air conditioning, and a private entrance. With its convenient location, comfortable rooms, and array of amenities, the Winchester Inn is the perfect choice for your stay in Ashland.
Food lovers will delight in the culinary offerings at the Winchester Inn. For a taste of American, French, and local cuisine, head to the Alchemy Restaurant and Bar. With its modern and romantic ambiance, this restaurant is the perfect place for a special dining experience. If you're in the mood for French cuisine and a steakhouse atmosphere, Chateaubriand 36 is the place to go. This family-friendly restaurant offers a delectable menu that will satisfy every palate.
At the Winchester Inn, your comfort is our top priority. That's why we offer a variety of room types to suit your needs. Whether you're traveling with your furry friend or looking for a spacious suite for your family, we have you covered. Each room is equipped with free WiFi, air conditioning, and a private entrance, ensuring that you have everything you need for a relaxing stay.
When it comes to payment options, we accept American Express, Discover, Visa, and Mastercard. Please note that cash is not accepted at the Winchester Inn. This convenient payment option makes it easy for you to settle your bill and enjoy a hassle-free stay.
Closest airports
Rogue Valley International - Medford Airport
14.6miGrants Pass Airport
40.9miKlamath Falls Airport
49.7miMost popular amenities
Pet Friendly
Free Private Parking
Free wifi
Spa tub
Air conditioning
Private entrance
Tennis court
Mountain view
Non-smoking rooms
Bar
Garden view
Restaurant
Garden
View
Terrace
Patio
Extra long beds (> 6.5 ft)
Free toiletries
Balcony
Bathtub
Private Bathroom
Parking On Site
Rooms
Two-Bedroom Suite
1 Queen Size Bed
1 Sofa Bed
1 King Size Bed
905 sqft
City view
Private Bathroom
Private entrance
Microwave
x4
+
Experience utmost comfort and luxury in our Two-Bedroom Suite, spanning 904 sqft, designed to accommodate 4 adults and 2 children. Enjoy city views from your private patio, unwind in the spacious living area, and indulge in the suite's array of premier amenities, including a flat-screen TV, coffee machine, and more.
Superior King Suite
1 King Size Bed
905 sqft
Mountain view
Spa tub
Garden view
City view
Indulge in the spaciousness and luxury of our Superior King Suite, boasting 904 sqft of living space. Unwind in the spa tub or soak up stunning mountain, garden, and city views from your private balcony. With a range of top-notch amenities and a plush king-size bed, your comfort is our priority.
Queen Room
1 Queen Size Bed
355 sqft
Garden view
Private Bathroom
Private entrance
Minibar
Stay in our Queen Room, a spacious and comfortable double room with beautiful garden views and a private entrance. Enjoy amenities like a minibar, flat-screen TV, and patio, ensuring a relaxing and enjoyable stay.
King Room with Balcony
1 King Size Bed
420 sqft
Mountain view
Garden view
City view
Private Bathroom
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.
Family Room
1 King Size Bed
1 Sofa Bed
355 sqft
Mountain view
Garden view
City view
Private Bathroom
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.
Comfort Triple Room with Shower
1 Twin Bed
1 King Size Bed
355 sqft
Garden view
Private Bathroom
Minibar
Coffee machine
Experience comfort and luxury in our spacious Comfort Triple Room with a stunning garden view. With a private bathroom, a flat-screen TV, and a minibar, this room promises to provide relaxation and all the necessary amenities for a memorable stay.
Queen Room
1 Sofa Bed
1 Queen Size Bed
355 sqft
Garden view
City view
Private Bathroom
Minibar
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.
Deluxe King Suite
1 King Size Bed
1 Sofa Bed
495 sqft
Spa tub
Garden view
Private Bathroom
Bathtub
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.
Deluxe King Studio
1 King Size Bed
450 sqft
Mountain view
Spa tub
City view
Private Bathroom
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.
Triple Room with Bath
1 Twin Bed
1 King Size Bed
355 sqft
Garden view
Private Bathroom
Bathtub
Private entrance
Experience luxury and comfort in our spacious Triple Room with Bath. Unwind and enjoy the garden view from your private patio, indulge in a relaxing bath in the bathtub, and have a peaceful night's sleep on our extra long beds. Amenities such as a minibar, coffee machine, and flat-screen TV are also provided for your convenience.
King Room
1 King Size Bed
1 Sofa Bed
400 sqft
Garden view
Private Bathroom
Bathtub
Private entrance
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.
King Room
1 King Size Bed
355 sqft
Garden view
Private Bathroom
Private entrance
Minibar
Experience a truly luxurious stay in our spacious King Room, featuring a stunning garden view, a private bathroom, a comfortable king-size bed, and top-notch amenities including a minibar, coffee machine, and flat-screen TV. Unwind and relax in this stylish room, perfect for couples seeking a peaceful retreat.
Double Room with Garden View
1 Queen Size Bed
355 sqft
Garden view
Private Bathroom
Minibar
Coffee machine
"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)
Standard Queen Room
1 Queen Size Bed
300 sqft
Garden view
Private Bathroom
Balcony
Bathtub
Experience relaxation and comfort in our spacious 301 sqft Standard Queen Room. Enjoy a peaceful garden view from your private balcony, unwind in the bathtub, and indulge in the convenience of a minibar and coffee machine, making it the perfect retreat for couples.
King Room
1 King Size Bed
355 sqft
Garden view
Private Bathroom
Balcony
Bathtub
Experience ultimate comfort in our spacious King Room with its garden view and private balcony. Relax in the bathtub, enjoy a cup of coffee from the in-room coffee machine, and unwind with a movie on the flat-screen TV. With amenities like a minibar, air conditioning, and free toiletries, you'll have everything you need for a relaxing stay.
Suite with Garden View
1 Queen Size Bed
1 Sofa Bed
400 sqft
Mountain view
Spa tub
Garden view
Private Bathroom
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.
King Suite
1 King Size Bed
450 sqft
Spa tub
Garden view
Private Bathroom
Bathtub
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.
Deluxe King Suite
1 King Size Bed
450 sqft
Spa tub
Garden view
City view
Private Bathroom
Indulge in luxury with our Deluxe King Suite, boasting a spacious 452 sqft size, a spa tub for ultimate relaxation, and stunning views of the garden or city. Enjoy a comfortable stay with a plush king-size bed, private bathroom with bathtub, and a range of amenities including a minibar, coffee machine, and flat-screen TV.
Queen Studio
1 Sofa Bed
1 Queen Size Bed
400 sqft
Spa tub
Garden view
Private Bathroom
Bathtub
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.
Queen Suite
1 Queen Size Bed
1 Sofa Bed
400 sqft
Mountain view
City view
Private Bathroom
Bathtub
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.
King Suite
1 King Size Bed
1 Sofa Bed
450 sqft
City view
Private Bathroom
Private entrance
Minibar
Indulge in a luxurious stay in our King Suite, a spacious 452 sqft room with a city view. Fall in love with the plush King size bed and unwind in the private bathroom, equipped with a shower and free toiletries. Enjoy added amenities such as a minibar, coffee machine, and flat-screen TV to enhance your stay.
Guest reviews
9.3
328 reviewsFrom
$208Categories of assessments
Cleanliness
Comfort
Location
Facilities
Staff
Value for money
WiFi quality
Breakfast
Featured reviews:
🇺🇸
David
8.2
8.2
It’s a lovely place., and its only two blocks from the Shakespeare Festival. The staff is wonderful! The free breakfasts are delicious. Plus they give you lots of choices. We sat on the large front porch to eat and had a deer join us for breakfast. The mattress and sheets are so soft and comfortable. The bathroom has a nice sized tub and a large walk-in separate shower. They have nice touches like bringing you a treat every day.
The lack of parking is a problem. We were didn’t take the car out during the day for fear we wouldn’t get a spot when we returned. I would definitely book a room with a kingsized bed. We had a queen bed, which felt so small. It fell more like a double bed. We couldn’t get our tv to work. They tried to fix it, but it never got resolved.
🇺🇸
Terry
10
10
Breakfast was fabulous - both times! The first morning we had an early morning appointment so the staff fixed us up with a beautiful set of boxed breakfasts - fresh fruit, divinely cooked soft boiled eggs, prosciutto and the most lovely blue cheese slabs - a culinary delight! The second morning we were able to eat in the restaurant downstairs which provided a very nice menu featuring oatmeal, eggs benedict, pumpkin pancakes, and the delicious 3-cheese, french mushroom omlette which was my choice. Also accompanying our meal was a delicious scone, fresh berries and a superb lemon curd spread, with Mimosas or Bloody Marys available upon request. In our room I loved the sunny window seat and spacious suite overlooking the garden. The bathroom was made of opulent marble, with a separate sink/vanity out in the bedroom. Walking to the cabaret next door was easy and we loved the short stroll. The staff was thoughtful and attentive to our every need. They even called us early in the day of our arrival to let us know our room was prepared and ready to receive us.
🇺🇸
Nazhin
8.2
8.2
Breakfast was AMAZING!! Included with the room and made to order. The food was exceptionally delicious and the staff was super friendly. The location is so quaint with great access to downtown. People are relaxed on the veranda or reading newspapers on their balconies. Great vegetation. Very calming and enjoyable.
We really enjoyed our stay at the Winchester Inn. If we had to choose something we didn't like it was possibly that you had to climb a narrow flight of stairs to get to the room but that was offset by the charm of the location.
🇺🇸
Becky
10
10
Beautiful room with a fireplace and a spacious bathroom with a large spa tub. Cozy robes, a personalized welcome message, a rose, and welcome cookies for two were special touches. My husband surprised me with their in house package of a beautiful bouquet of roses and a plate handmade truffles to celebrate our 25th wedding anniversary. We enjoyed the gourmet breakfasts in their lovely dining room with friendly staff. We felt very welcomed and pampered! Highly recommended!
🇺🇸
Alyse
8.2
8.2
Breakfast quality was great and the room was quiet and comfortable.
Disliked that they would charge extra for certain items for the supposed “complementary” breakfast. Either include them or don’t. That plus the fact that they wanted to charge $5.00 for a small bottle of water in the room (that was $300/ night!) rather than offering a couple bottles of complimentary water like every other nice hotel made us feel nickeled and dimed. It wasn’t alcohol! But then they actually wanted $35 for a half bottle of wine. Ridiculous, so we passed.
🇺🇸
Jacquelyn
8.2
8.2
Staff was great! Very welcoming and helpful. Breakfast was excellent!
There are stairs and uneven ground to navigate. Not the best for two seniors with some mobility issues. We managed. A word of caution, the vanity in our room was not flush with the wall and I unfortunately dropped an item and it rolled under the vanity. I ultimately had to borrow my husband's cane to get it out ... along with a couple of stray dust bunnies and someone's random pill. All in all we would stay again.
🇺🇸
Walter
10
10
The breakfast was superb -- not only the food, but the service, the atmosphere, the overall feeling. Everything about the place was first class, from the comfortable room, the shower with bathrobe provided, the well-stocked fridge/bar, the little extras like fruit tarts to munch on when we checked in. All the staff were super friendly and helpful. Absolutely a wonderful place to stay.
Nothing could have been done to improve our stay. It was great.
🇺🇸
Brittany
10
10
The inn was fantastic! The room big and spacious with fresh cookies left nightly. The included breakfast every morning was impeccable and left me excited for waking up. Location was so convenient- close enough to downtown there was no need for a car but tucked away enough to have peace and quiet.
My only feedback was the pillows in the room were really small and I did wake up with a sore neck. Otherwise the room was so cozy it was hard to leave!
🇺🇸
Margaret
10
10
This place is fabulous and is good enough to be a destination by itself! It is, however, in walking distance of all the downtown shops and theaters that make Ashland a travel destination, and is an easy walk to Lithia park, which is wonderful.
There is nothing not to like about this place. It also includes breakfast, which is not your run of the mill fare, but a menu ordered divine meal of your choosing.
🇺🇸
Gretchen
10
10
Breakfast is terrific Staff are so lovely Sitting in. The garden area is dreamy The style is charming Bar is splendid - best looking bar anywhere The dinner in-house was marvelous Staff work so hard to connect with guests and offer A joyful hospitality. We are loyal fans.
The bed was uneven and bit uncomfortable in Catherine M That’s all - everything else is so lovely
Points of Interest Around Winchester Inn
Attractions
Rogue River
14.2miAttractions
Rogue River
14.2miAirports
Rogue Valley International - Medford Airport
14.6miGrants Pass Airport
40.9miKlamath Falls Airport
49.7miRestaurants
Alchemy Restaurant and Bar
Cuisines
American•French•Local•InternationalAmbiances
Modern•RomanticChateaubriand 36
Cuisines
French•SteakhouseAmbiances
Family FriendlyAmenities of Winchester Inn
Pet Friendly
Free Private Parking
Free wifi
Spa tub
Air conditioning
Private entrance
Tennis court
Mountain view
Non-smoking rooms
Bar
Garden view
Restaurant
Garden
View
Terrace
Patio
Extra long beds (> 6.5 ft)
Free toiletries
Balcony
Bathtub
Private Bathroom
Parking On Site
Amenities of Winchester Inn
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
Ironing facilities
Non-smoking rooms
Pet Friendly
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
Safety features
Shared stationery (e.g. printed menus, magazines, pens, paper) removed
Services
Wake-up service/Alarm clock
View
City view
Garden view
Inner courtyard view
Mountain view
View
Stay rules - Winchester Inn
From
$208Check-in
From 16:00
Check-out
Until 11:00
Pets
Pets are not allowed.
Internet
WiFi is available in all areas and is free of charge.
Age restrictions
There's no age requirement for check-in
Curfew
Come and go whenever you want
Parking
Free private parking is available on site (reservation is not needed).
Reservations
Call us for our best daily rates
+1-833-728-2041Children and beds
Child policies
Children of all ages are welcome.
Children 9 and above are considered 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.
Cards accepted at this property
Discover,
American Express,
Visa,
Mastercard
This property does not accept cash.
Check-in / Check-out
Pets
Internet
Age restrictions
Curfew
Parking
Reservations
Children and beds
Cards accepted at this property
Frequently Asked Questions - Winchester Inn
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 $208. 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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