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The Winchester Inn

35 South Second Street , Ashland, OR 97520 USA (Show map)
4.6
258 Reviews
$90 - $405
per night

Check Dates

About

The Winchester Inn offers affordable excellence with an attention to detail and comfort; while the restaurant and wine bar offer innovative cuisine, award wining wine lists, and attentive service in a warm cozy atmosphere. This traditional Victorian stately home is in perfect harmony with its surroundings, situated in the midst of an English country garden. As guests approach the main building pansies line the path that leads to the front entrance, the gardens are encompassed by a herbaceous border whilst colorful tulips are scattered throughout the grounds. The interior is no less stunning, the rooms are a tribute to comfort and subtlety, with soft, warm shades and opulent furniture. Dinner may be taken in the popular restaurant, whilst in the summer, food is served outdoors. Wherever guests dine, the sumptuous flavors and textures are of the highest standards. The new wine bar provides a nice tasting of local wineries and a special nightly wine flight. The quaint gazebo is a perfect site for small weddings and receptions. Sporting activities available nearby include fishing, golf, ballooning or skiing while the more artistic guest may wish to visit the Ashland Shakespeare Festival or the Britt Music Festival, information on which may be obtained from the inn. If you are unable to find rooms through BedandBreakfast, please check out our personal availability calendar or call us to double check.

Rooms & Rates

Garden Room

The Garden Room (located on the second floor of the Main House) with its beautiful bay window overlooking the tiered gardens, has a queen size bed and a private bath with an antique claw foot tub. Soft blue greens and white highlight this room.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$140 - $205 Nightly Rate: $140 - $205

Sylvan Room

The Sylvan Room with its large bay window and pillow filled window seat, look over a 60 year old alomond tree. decorated in muted shades of soft green and beige.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 Queen

$140 - $205 Nightly Rate: $140 - $205

Queen Anne Room

The Queen Anne Room, luxurious with a both feather bedded queen bed and twin and a half canopy over the queen. This room boasts a suite of antique furniture that sets the soft tones of yellow and green to a picture perfect finish The private bath includes an antique claw foot tub.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 Queen , 1 Twin

$140 - $205 Nightly Rate: $140 - $205

Fordyce Suite

The Fordyce Suite is our newest renovation, located in the Main House on the second floor overlooking the garden and gazebo. The suite has a two person jetted tub, in a luxurious bathroom of travertine marble. The suite also features a king size bed, feather bed, a fireplace, TV, stereo and wet bar.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $190 - $299

Sunset Room

The Sunset Room has a queen size bed with feather bed and a private bath with a shower. French doors open onto a balcony where our guests enjoy the beautiful sunset over the hills of Ashland. This room is restful in shades of blue and salmon.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $140 - $195

Patio Room

The Patio Room has a queen size bed with feather bed, private bath with antique claw foot tub. The private entrance opens upon a semi-secluded patio with a fountain. This room is fresh in florals and shades of, green, and peach.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$140 - $205 Nightly Rate: $140 - $205

Eastlake Room

The Eastlake Room, has a queen size bed, with feather bed private bath and antique claw foot tub. Enjoy a private entrance from the garden walkway. This room is decorated in shades of taupe with burgundy and cream toile with forest greens.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$140 - $205 Nightly Rate: $140 - $205

Enders Room

The Enders Room is spacious and has two beds, a king and a twin both topped with feather beds. The private bath has a conventional tub and shower. There is a convenient entrance from the garden path. This room is appointed in neutrals and sage green tones.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King , 1 Twin

$140 - $205 Nightly Rate: $140 - $205

Robert Gordon Suite

The Robert Gordon is a deluxe suite featuring a spacious sitting room, with a fireplace, tv stereo, honor bar which adjoins the bedroom with a king size bed topped with a feather bed, private bath with a one-person jetted tub. Florals and shades of burgundy, cream, and pinks decorate the room. French doors open out to a garden walkway. Wheelchair accessible.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 King

$190 - $299 Nightly Rate: $190 - $299

Peter Benjamin Room

The Peter Benjamin Room with its king size bed topped with a feather bed. Private bath A large room with a sitting area, offering a sofa that opens to a full bed. Outside the room is a large deck with fountain and gardens This room is decorated in florals and shades of green and beige.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 King

$140 - $205 Nightly Rate: $140 - $205

Marjorie Roy Room

The Marjorie Roy has a queen size bed with feather bed. A beautiful bay window allows for sunshine and a pleasant view. There is also a small balcony for our guests to enjoy. The room is trimmed in shades of green, white, and burgundy and a rollaway is possible, but a snug fit in this room.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$140 - $205 Nightly Rate: $140 - $205

Catharine M. Room

The Catharine M. has a queen size bedwith feather bed. Private bath. The balcony is shared with the Andrew G.which is next door. This room is decorated in beige and pinks.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$140 - $205 Nightly Rate: $140 - $205

Andrew G.

The Andrew G. (located in The Heritage House) has a queen size bedwith feather bed as well as a sofa hide-a-bed. This room is finished in florals and shades of green and white. A small balcony is shared with the Catharine M.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 Queen

$140 - $205 Nightly Rate: $140 - $205

Eleanor Rose Suite

The Eleanor Rose Suite is a spacious suite with high vaulted ceiling, king size bed with feather bed. A fireplace with TV stereo and honor bar and coffee maker ar a part of this suite. A private bath with a jetted tub for two plus shower. This room is lovely in shades of beige, cream, and accents of blue, and can accommodate a rollaway.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King

$190 - $299 Nightly Rate: $190 - $299

Barbara Howard Suite

The Barbara Howard Suite is located at the front of the building. It has a king size bed with feather bed a two person shower and two-person jetted tub. This suite has an intimate sitting area with a fireplace, TV stereo, honor bar, coffee maker and window seat. The room is charmingly appointed in florals and shades of beige and green. A rollaway is possible, but it is snug.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King

$190 - $299 Nightly Rate: $190 - $299

Courtyard Suite

Set into the tiered gardens the Courtyard Suite offers a queen size bed with feather bed as well as a sofa hide-a-bed. Wet bar , coffee maker, TV and stereo The bath has a large two person jetted tub and seperate shower. The Courtyard has a stunning view of the gardens and gazebo and French doors open to a lovely garden walkway. Burgundy, white, and green bring the gardens into this room.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 Queen

$190 - $299 Nightly Rate: $190 - $299

Belvedere Suite

The Belvedere Suite is located on the second floor of the Larkspur Cottage has a queen size bed with feather bed and fireplace, wet bar with honor bar, coffee maker, TV and stereo. A beautiful bay window seat overlooks the gardens and gazebo with lovely views of the valley. This suite is light and airy revealing the floral prints and shades of green, white, and pastels to their best advantage. A rollaway is possible in this room.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$190 - $299 Nightly Rate: $190 - $299

Brighton Suite

The Brighton Suite is located in The Carriage House, this two room suite offers a seperate living room with sofa bed,fireplace and wet bar, TV and stereo. The bedroom has a queen bed with feather bed. A private bath offers a spa shower.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 Queen

$190 - $299 Nightly Rate: $190 - $299

Silverdale Suite

Silverdale Suite, with its high vaulted ceilings and hard wood floors, offers a full living room,fireplace, wet bar, tv and stereo A queen size bed topped with a feather bed in the bedroom. Private bath with soaking tub and large walk-in shower. Shades of burgundy and green accent this suite.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $190 - $299

Guest Rooms

Guest rooms offer at least a queen size bed with private bath. Full two course gourmet breakfast is included with your stay.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $140 - $195

Suites

Suites are larger than guest rooms with queen or king size beds. Some suites have jacuzzi tubs and fire places. All suites come with TVs and include a two course gourmet breakfast in the morning.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $190 - $295

Check Dates Visit Website

Reviews

Overall
4.6

Write A Review

  • Guest room4.6
  • Service4.7
  • Value4.2
  • Cleanliness4.7
  • Dining4.7

Score Breakdown based on
258 Reviews

Write A Review

great weekend

4.6 on October 20, 2014

A great find in the center of Ashland. Staff could not have been nicer.


Winchester Inn--The Perfect Stay in Ashland

5 on October 15, 2014

We try to stay at the Winchester each year when we return to Ashland for the Oregon Shakespeare Festival. It is so popular that one must book well in advance. The Sunset Room is a real bargain for the price, and it has a very nice balcony for viewing the city and a bed that requires a small two step assistance to get up into the bed. And the bed is luxurious--fit for a queen. The Winchester is so convenient to the theaters--it is only a few minutes comfortable walk, which is a real convenience after the evening outdoor performance. The rooms are comfortable and nicely appointed. Everything is spotless and well-maintained. The staff is so friendly and accommodating--appearing literally out of nowhere when one is hefting an oversize bag up or down the stairs to voluntarily do the heavy lifting for you. Breakfast comes with the room and it is an amazing morning treat. I cannot recall exactly what we had the last time, but it was scrumptous. Usually there is a fantastic fruit plate, scones, a very appealing egg dish, French Toast or Waffles. What a start to the day! Their dinners are equally as good, although we enjoy other restaurants in Ashland and ensure we get some variety. We cannot say enough good things about the Winchester. You must stay there to believe it.


Always a pleasure at Winchester Inn!

4.8 on October 14, 2014

The Winchester has become our home away from home when in Ashland for the Oregon Shakespeare Festival -- or for any other reason. We love it, and look forward as always to our next visit.


Always The Best

5 on October 10, 2014

We have stayed with The Gibbs at The Winchester Inn for many years and are always treated like one of the family. The food, service and rooms are the best in Ashland and as good as one can find anywhere in the West. The convenience to the Oregon Shakespeare Festival is also a plus because we park and never need a vehicle until we head out. Highly recommend staying here.


Another Exception Stay at The Winchester

4.8 on September 14, 2014

Have been staying at the Winchester for more than 10 years now every time we go to Ashland. It is consistently excellent. I book WAY in advance because the B & B is so deservedly spectacular.


Great Place to Stay

3.8 on September 07, 2014

We spent 2 nights in Peter Benjamin, a building adjoining the main building. The room was great. The bath was very spacious for a bed and breakfast. The breakfasts were unbelievable. The staff was most friendly. There was a small fire a few buildings away on a Saturday night and the Winchester kitchen staff put it out with their emergency fire extinguishers. We could not be more enthusiastic about our stay. We highly recommend the Winchester which is very conveniently located for the Oregon Shakespeare Festival Theaters.


The Best!!

4.6 on September 01, 2014

The Winchester Inn is simply one of the best places we have ever stayed. The Gibbs family is always welcoming and the rooms are terrific. The food is exceptional.


Ashland's Best Lodging!

4.8 on August 22, 2014

Beautiful, distinctive rooms in an ideal location--a short walk to theaters. The restaurant, Alchemy, is among the best in town. Beautiful gardens, friendly staff, nice amenities in suites.


Simply the Best

5 on August 18, 2014

The Winchester does everything right. Amazing attention to detail, providing comfort with warmth and charm. Its proximity to the Oregon Shakespeare Festival is an added bonus (3 minute walk). The Winchester is one of those places that charges a full price but feels like a bargain because it is perfect. We can't wait to go back.


Lovely Interlude in Busy Lives

4.8 on August 13, 2014

Delicious sheets and Robert the cat. Also wonderful breakfasts and close to OSF. It's spendy, but everything in Ashland is and the Winchester was worth the money. We will return next year.


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Location

Location Type

Downtown, Mountains, Small town, Wine country

Airport

Medford, OR (MFR-Medford-Jackson County) 20 miles

Directions to property:

Approx. 5 hours South from Portland, 6 hours North from San Francisco, 3 miles from I-5 East.

Area Attractions

Antique Shopping, Art Galleries, Concert venue, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Movie Theater, Museum, National/State parks, Nature area, Rogue Creamery, Oregon Shakespeare Festival, 50+ Local Wineries, Performing Theater, Picnic area, Religious Services, River, Ski area, Vineyard, Winery

Inn Details

Establishment type

Other, Country Inn, Urban Inn

On-site amenities

Copier, Fax Machine, Fireplace, Internet Service, Private entrance, Wedding Facilities , Imported 600 thread count sheets, Certified Sommelier on Staff

Room amenities

Air conditioning, Alarm clock, Amenities Basket, Bath robes, CD player, Coffee/Tea facilities, In-room internet, Hairdryer, Hot tub/whirlpool tub, Ironing Board, Radio, Satellite/Cable TV, TV, Telephone, Turndown Service, Wi-Fi

On-site activities

Bicycle riding trails, Cross-country ski trails, Downhill Skiing, Golfing, Hiking trails, Kayaking, Mountain Bike trails, Annual Dickens' Feast, Shopping, Ski rentals, Whitewater Rafting

Check Dates Visit Website

Policies

  • Check In:: 3:00 P.M.
  • Check Out:: 11:00 AM
  • Open All Year Round: Yes
  • Smoking Allowed: No
  • Drinking Allowed: Yes
  • [Resource Id: alcohol_provided, Set: propertyview] Yes
  • Suitable For Children: Yes
  • Childcare Provided: Limited Babysitting services are available upon request.
  • Guest Pets Allowed: No
  • [Resource Id: disabledaccess, Set: propertyview] Limited

Terms and Conditions

  • Deposit Amount Required: One nights pre payment is required for each reservation booked.
  • Cancellations: Please check upon reservation.

Innkeepers

Name(s)

Michael & Laurie Gibbs

Languages spoken

Some German, English

Resident Pets

None

Check Dates Visit Website

Meals

Breakfast

Gourmet two course breakfast

  • Time Served: 8:00-9:30 A.M.
  • Serving Location: Dining Room, Guest room

Special meal options

Low fat , Restrictive , Vegetarian , Gluten Free, Please inquire.


Signature Dish

Sous Vide Filet Mignon
Filet Mignon cooked sous vide with a Rogue Creamery Bleu Cheese and caramelized shallots compound butter and a sauce perigueux.


Recipes

Details

BedandBreakfast.com Diamond Collection

35 South Second Street , Ashland, OR 97520 USA (Show map)

Property highlights


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