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9.3

328 reviews

Winchester Inn

Winchester Inn

35 South 2nd Street, Ashland, 97520, Oregon, United States

Reservations:

+1-833-728-2041

Choose dates to view prices

Restaurant

Free Private Parking

Free wifi

Spa tub

Air conditioning

Tennis court

Bar

Private entrance

Winchester Inn

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 328 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

14.6mi

Grants Pass Airport

40.9mi

Klamath Falls Airport

49.7mi

Most popular amenities

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

Rooms

Show 2 photos

Anne, Queen

1 Queen Size Bed

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Duet Suite

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Standard Room

More details

King Room, Balcony

1 King Size Bed

Balcony

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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.

Studio, Queen

1 Queen Size Bed

1 Sofa Bed

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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 Room

1 Queen Size Bed

1 Sofa Bed

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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 Suite

1 King Size Bed

1 Sofa Bed

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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 Studio, King

1 King Size Bed

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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.

King Room

1 King Size Bed

1 Sofa Bed

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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.

Suite, Queen

1 Queen Size Bed

1 Sofa Bed

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.

Suite, Garden View

1 Sofa Bed

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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.

Suite, King

1 King Size Bed

1 Sofa Bed

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.

Guest reviews

9.3

328 reviews

Categories of assessments

Cleanliness

Comfort

Location

Facilities

Staff

Value for money

WiFi quality

Breakfast

Featured reviews:

🇺🇸

David

8.2

September 2023

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.

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Terry

10

August 2023

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.

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Nazhin

8.2

June 2023

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.

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Becky

10

August 2023

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!

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Alyse

8.2

March 2023

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.

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Jacquelyn

8.2

May 2023

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.

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Walter

10

August 2023

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.

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Brittany

10

June 2023

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!

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Margaret

10

August 2023

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.

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Gretchen

10

June 2023

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

14.2mi

Restaurants

Alchemy Restaurant and Bar

Cuisines

  • American
  • French
  • Local
  • International

Ambiances

  • Modern
  • Romantic

Chateaubriand 36

Cuisines

  • French
  • Steakhouse

Ambiances

  • Family Friendly

Amenities of Winchester Inn

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

Stay rules - Winchester Inn

  • 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 $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.