Title: Winchester Inn - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=1505812&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) # Winchester Inn Downtown Winchester Inn combines historic charm with warm hospitality, offering a peaceful garden retreat and freshly made breakfast before guests explore the area ## Photo gallery for Winchester Inn ![Bar (on property) - Winchester Inn (Ashland)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/684defd4.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Front of property - Winchester Inn (Ashland)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/a65795fb.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Suite, 1 King Bed (Barbara Howard) - Winchester Inn (Ashland)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/815c2dcc.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Suite, 1 Bedroom (Silverdale) | Living area - Winchester Inn (Ashland)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/a170cf24.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area - Winchester Inn (Ashland)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/30df7c7a.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Rooms - Location - Policies Located in the Historic Downtown District, Winchester Inn welcomes travelers with a charming garden and sunny terrace. Enjoy a cooked-to-order breakfast, WiFi, and convenient dry cleaning services. The helpful staff and bar provide perfect spots for relaxation. ## Reviews 9.8 Exceptional ## Popular amenities - Parking included - Free WiFi - Air conditioning - Business services ## Room options ### Check availability for these dates Tonight [Dec. 24 - Dec. 25](https://www.expedia.ca/Hotel-Search?startDate=2025-12-24&endDate=2025-12-25&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-24&endDate=2025-12-25&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) Tomorrow [Dec. 25 - Dec. 26](https://www.expedia.ca/Hotel-Search?startDate=2025-12-25&endDate=2025-12-26&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-25&endDate=2025-12-26&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) This weekend [Dec. 26 - Dec. 28](https://www.expedia.ca/Hotel-Search?startDate=2025-12-26&endDate=2025-12-28&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-26&endDate=2025-12-28&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) Next weekend [Jan. 2 - Jan. 4](https://www.expedia.ca/Hotel-Search?startDate=2026-01-02&endDate=2026-01-04&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-02&endDate=2026-01-04&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) All rooms 1 bed 2 beds 3+ beds Showing 20 of 20 rooms ### View all photos for Double Room, 1 Bedroom (Garden) ![Double Room, 1 Bedroom (Garden)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/0cfbcd24.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room, 1 Bedroom (Garden) 10.0 Exceptional 1 review ### Highlights Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding Premium bedding - 350 sq ft - 1 bedroom - Sleeps 2 - 1 Queen Bed ### View all photos for Double Room, 1 Bedroom (Sylvan) ![Double Room, 1 Bedroom (Sylvan)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/4b42fd02.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room, 1 Bedroom (Sylvan) 9.6 Exceptional 5 reviews ### Highlights Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding Pillowtop bed - 350 sq ft - 1 bedroom - Sleeps 2 - 1 Queen Bed and 1 Double Sofa Bed ### View all photos for Double Room (Queen Anne) ![Double Room (Queen Anne)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/e69caa9d.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room (Queen Anne) 10.0 Exceptional 1 review ### Highlights Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding Egyptian cotton linens - 350 sq ft - Sleeps 2 - 1 Queen Bed and 1 Twin Bed ### View all photos for Double Room, 1 Queen Bed (Patio) ![Double Room, 1 Queen Bed (Patio)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/639710ad.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room, 1 Queen Bed (Patio) 9.4 Exceptional 3 reviews ### Highlights Balcony or patio Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding - 350 sq ft - Sleeps 2 - 1 Queen Bed ### View all photos for Double Room, 1 Queen Bed (Marjorie Roy) ![Double Room, 1 Queen Bed (Marjorie Roy)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/64377705.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room, 1 Queen Bed (Marjorie Roy) ### Highlights Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding Egyptian cotton linens - 350 sq ft - Sleeps 2 - 1 Queen Bed ### View all photos for Double Room, 1 Queen Bed (Catharine M) ![Double Room, 1 Queen Bed (Catharine M)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/187c0e62.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room, 1 Queen Bed (Catharine M) 10.0 Exceptional 5 reviews ### Highlights Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding Egyptian cotton linens - 300 sq ft - Sleeps 2 - 1 Queen Bed ### View all photos for Double Room, 1 King Bed (Sunset) ![Double Room, 1 King Bed (Sunset)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/050f6f51.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room, 1 King Bed (Sunset) 10.0 Exceptional 2 reviews ### Highlights Furnished balcony Individually furnished Individually decorated Fireplace Air conditioning Heating Free rollaway/extra beds Flat-screen TV - 400 sq ft - Sleeps 2 - 1 King Bed ### View all photos for Double Room, 1 King Bed (Andrew G) ![Double Room, 1 King Bed (Andrew G)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/36c62c53.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room, 1 King Bed (Andrew G) 10.0 Exceptional 3 reviews ### Highlights Furnished balcony Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding - 400 sq ft - Sleeps 2 - 1 King Bed ### View all photos for Double Room, 1 King Bed (Peter Benjamin) ![Double Room, 1 King Bed (Peter Benjamin)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/76811976.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room, 1 King Bed (Peter Benjamin) ### Highlights Furnished patio Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding - 400 sq ft - Sleeps 2 - 1 King Bed ### View all photos for Double Room, 1 King Bed (Eastlake) ![Double Room, 1 King Bed (Eastlake)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/db18b181.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room, 1 King Bed (Eastlake) 10.0 Exceptional 1 review ### Highlights Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding Egyptian cotton linens - 350 sq ft - Sleeps 2 - 1 King Bed ### View all photos for Double Room, 1 King Bed (Enders) ![Double Room, 1 King Bed (Enders)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/fa2f4166.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Double Room, 1 King Bed (Enders) 10.0 Exceptional 1 review ### Highlights Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding Egyptian cotton linens - 400 sq ft - Sleeps 2 - 1 King Bed ### View all photos for Suite, 1 King Bed with Sofa bed (Robert Gordon) ![Suite, 1 King Bed with Sofa bed (Robert Gordon)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/9351d686.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Suite, 1 King Bed with Sofa bed (Robert Gordon) 7.0 Good 2 reviews ### Highlights Separate sitting area Individually furnished Individually decorated Fireplace Air conditioning Heating Free rollaway/extra beds Flat-screen TV - 500 sq ft - 1 bedroom - Sleeps 2 - 1 King Bed and 1 Double Sofa Bed ### View all photos for Suite, 2 Bedrooms (Duet Suite) ![Suite, 2 Bedrooms (Duet Suite)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/16742498.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Suite, 2 Bedrooms (Duet Suite) ### Highlights Furnished patio Separate sitting area Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV - 700 sq ft - 2 bedrooms - Sleeps 4 - 1 King Bed, 1 Queen Bed and 1 Double Sofa Bed ### View all photos for Suite, 1 King Bed (Hargadine) ![Suite, 1 King Bed (Hargadine)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/15d7e5a9.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Suite, 1 King Bed (Hargadine) ### Highlights Furnished balcony Separate sitting area Individually furnished Individually decorated Fireplace Air conditioning Heating Free rollaway/extra beds - 900 sq ft - 1 bedroom - Sleeps 2 - 1 King Bed ### View all photos for Suite, 1 King Bed (Barbara Howard) ![Suite, 1 King Bed (Barbara Howard)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/f2c18ffa.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Suite, 1 King Bed (Barbara Howard) ### Highlights Individually furnished Individually decorated Fireplace Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding - 500 sq ft - Sleeps 2 - 1 King Bed ### View all photos for Suite, 1 King Bed (Eleanor Rose) ![Suite, 1 King Bed (Eleanor Rose)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/92bdf1ac.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Suite, 1 King Bed (Eleanor Rose) 9.0 Wonderful 2 reviews ### Highlights Individually furnished Individually decorated Fireplace Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding - 500 sq ft - Sleeps 2 - 1 King Bed ### View all photos for Suite, 1 Bedroom (Silverdale) ![Suite, 1 Bedroom (Silverdale)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/c44ee8a3.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Suite, 1 Bedroom (Silverdale) 8.0 Very good 1 review ### Highlights Separate sitting area Individually furnished Individually decorated Fireplace Air conditioning Heating Free rollaway/extra beds Flat-screen TV - 450 sq ft - 1 bedroom - Sleeps 2 - 1 Queen Bed and 1 Twin Murphy Bed ### View all photos for Suite, 1 Queen Bed with Sofa bed (Brighton) ![Suite, 1 Queen Bed with Sofa bed (Brighton)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/6f78a581.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Suite, 1 Queen Bed with Sofa bed (Brighton) ### Highlights Separate sitting area Individually furnished Individually decorated Fireplace Air conditioning Heating Free rollaway/extra beds Flat-screen TV - 450 sq ft - 1 bedroom - Sleeps 2 - 1 Queen Bed and 1 Double Sofa Bed ### View all photos for Suite, 1 Queen Bed with Sofa bed (Courtyard) ![Suite, 1 Queen Bed with Sofa bed (Courtyard)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/60135df8.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Suite, 1 Queen Bed with Sofa bed (Courtyard) ### Highlights Furnished patio Individually furnished Individually decorated Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding - 450 sq ft - Sleeps 2 - 1 Queen Bed and 1 Double Sofa Bed ### View all photos for Suite, 1 King Bed (Fordyce) ![Suite, 1 King Bed (Fordyce)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/df8f4911.jpg?impolicy=fcrop&w=1200&h=800&quality=medium) ### Suite, 1 King Bed (Fordyce) 10.0 Exceptional 1 review ### Highlights Individually furnished Individually decorated Fireplace Air conditioning Heating Free rollaway/extra beds Flat-screen TV Hypo-allergenic bedding - 450 sq ft - Sleeps 2 - 1 King Bed ![Mod logo](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Sign in to view eligible discounts and perks. 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[Sign in](https://www.expedia.ca/login?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMedford-Hotels-Winchester-Inn.h1505812.Hotel-Information)[Sign up, it's free](https://www.expedia.ca/signup?enable_registration=true&uurl=e3id%3Dredr%26rurl%3D%2FMedford-Hotels-Winchester-Inn.h1505812.Hotel-Information) ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C42.19477%2C-122.71198&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=pH8RZZBwRQ4AzE-uNSyJN23luwg=) 35 S. 2nd St., Ashland, OR, 97520 #### What's nearby - Oregon Cabaret Theatre \- 1 min walk \- 0.0 km - Allen Elizabethan Theatre \- 3 min walk \- 0.3 km - Thomas Theatre \- 3 min walk \- 0.3 km - Lithia Park \- 3 min walk \- 0.3 km - Oregon Shakespeare Festival \- 3 min walk \- 0.3 km #### Getting around - Rogue Valley Intl. Airport (MFR) - 22 min drive #### Restaurants - ‪Martolli's Hand Tossed Pizza - ‬5 min walk - ‪Ruby's - ‬6 min walk - ‪The Growler Guys - ‬3 min walk - ‪Zoey's Cafe - ‬3 min walk - ‪Taqueria Picaro - ‬4 min walk ## About this property ### Winchester Inn Inn located in Historic Downtown District You can look forward to free cooked-to-order breakfast, a terrace, and a garden at Winchester Inn. Free in-room WiFi is available to all guests, along with dry cleaning/laundry services and a bar. You'll also find perks like: - Free self parking - 1 meeting room, tour/ticket assistance, and concierge services - Luggage storage, smoke-free premises, and free newspapers - Guest reviews give top marks for the helpful staff Room features All guestrooms are individually furnished, and feature comforts such as premium bedding and air conditioning, in addition to thoughtful touches like free WiFi and bathrobes. Extra conveniences in all rooms include: - Heating and fans - Hypo-allergenic bedding, Egyptian cotton sheets, and pillowtop mattresses - Designer toiletries and hair dryers - Flat-screen TVs with cable channels - Wardrobes/closets, electric kettles, and daily housekeeping ## Similar properties ![Front of property](https://images.trvl-media.com/lodging/16000000/15160000/15153100/15153095/c4aac0d0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### McCall House Boutique Inn Historic Downtown District - Breakfast included - Parking included - Free WiFi - Air conditioning 9.2 Wonderful 580 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-07&endDate=2026-01-08&selected=15153095&PinnedHotelID=15153095&HadPinnedHotel=true®ionId=-1&adults=2) ![Garden](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Ashland Springs Hotel Historic Downtown District - Spa - Pet friendly - Parking included - Free WiFi 9.2 Wonderful 1,001 reviews CA $119 CA $153 total includes taxes & fees Jan 4 - 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Jan 1, 2026 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-31&endDate=2026-01-01&selected=95265593&PinnedHotelID=95265593&HadPinnedHotel=true®ionId=-1&adults=2) ![Abigail Rockefeller](https://images.trvl-media.com/lodging/5000000/4970000/4966500/4966403/996815d3.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Abigail’s Bed & Breakfast Inn Skidmore Academy Historic District - Parking included - Free WiFi - Air conditioning - Breakfast available 9.4 Exceptional 62 reviews CA $246 CA $275 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-03&endDate=2026-01-04&selected=4966403&PinnedHotelID=4966403&HadPinnedHotel=true®ionId=-1&adults=2) ## Property amenities ### Internet - Available in all rooms: Free WiFi - Available in some public areas: Free WiFi ### Parking and transportation - Free self parking on site - Limited onsite self parking ### Food and drink - Free cooked-to-order breakfast available daily 8:00 AM to 9:30 AM - A bar/lounge - A restaurant ### Conveniences - Free newspapers in lobby - Gift shop/newsstand - Limited-hour front desk - Luggage storage ### Guest services - Concierge services - Dry cleaning/laundry service - Housekeeping (daily) - Tour and ticket assistance ### Business services - Meeting room ### Outdoors - Garden - Terrace ### Accessibility - If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking. - No elevator - Wheelchair accessible (may have limitations) ### More - 3 floors - 5 buildings - Built in 1886 - Smoking not allowed - Victorian architecture ## Room amenities ### Bedroom - Down comforter - Egyptian cotton sheets - Hypo-allergenic bedding - Pillowtop mattress ### Bathroom - Bathrobes - Designer toiletries - Hair dryer - Towels provided ### Entertainment - Flat-screen TV with cable channels ### Food and drink - Coffee/tea maker - Electric kettle - Minibar ### More - Air conditioning - Fan - Heating - Individual decor - Individual furnishings - Iron/ironing board - Phone ## Policies ### Check-in Check-in start time: 4:00 PM; Check-in end time: 9 PM Late check-in subject to availability Minimum check-in age: 21 ### Check-out Check-out before 11 AM A late check-out fee will be charged ### Special check-in instructions The front desk is open daily from 7:30 AM - 8 PM Front desk staffed during limited hours Information provided by the property may be translated using automated translation tools ### Access methods Front desk (limited hours) ### Pets Pets not allowed ### Children and extra beds Children are welcome Cribs (infant beds) are not available ### Property payment types ## Important information ### Fees You'll be asked to pay the following charges at the property. Fees may include applicable taxes: - A tax is imposed by the city: USD 9.0 - 3 percent destination fee will be charged - Administrative fee: USD 6.00 per accommodation, per night We have included all charges provided to us by the property. ### Optional extras - A late check-out fee will be charged The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change. ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed This property accepts credit cards; cash is not accepted This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room ### We should mention This property does not have elevators Only registered guests are allowed in the guestrooms ### Property is also known as Winchester Inn Ashland Winchester Ashland The Winchester Inn Winchester Inn Inn Winchester Inn Ashland Winchester Inn Inn Ashland ## Frequently asked questions ### Is Winchester Inn pet-friendly? ### How much does it cost to stay at Winchester Inn? ### How much is parking? ### What time is check-in at Winchester Inn? ### What time is check-out at Winchester Inn? ### Where is Winchester Inn located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Reviews ## Winchester Inn Reviews 9.8 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) ### 9.8 Cleanliness ### 9.6 Location ### 9.8 Staff & service ### 9.4 Eco-friendliness ### 9.6 Property conditions & facilities 10 - Excellent 226 8 - Good 27 6 - Okay 4 4 - Poor 3 2 - Terrible 2 ## Reviews ### 10/10 Excellent #### Laura Sep 16, 2025 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again! ##### Laura Stayed 1 night in Sep 2025 ### 10/10 Excellent #### Carolyn Oct 26, 2025 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Beautiful room with comfortable bed. Nice quality bedding. ##### Carolyn Stayed 1 night in Oct 2025 ### 10/10 Excellent #### Christi Aug 30, 2025 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Such a unique Victorian place! So charming, clean and spacious…. ![](https://a.travel-assets.com/ugc/hotel-reviews/5656f1c1-5ec3-41e8-8fec-689c25815fe9-1756517693818.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/3f3f5148-04c9-46c3-9bbc-67c15a1ed8cd-1756517702115.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/b035b505-9fbf-4470-b544-5b397e36d2d1-1756517697938.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ##### Christi Stayed 2 nights in Aug 2025 ### 10/10 Excellent #### Dirk Jul 2, 2025 Liked: Cleanliness, staff & service, property conditions & facilities Beautiful property, really comfortable bed, pillows and sheets! ##### Dirk Stayed 1 night in Jun 2025 ### 10/10 Excellent #### Nick Jul 23, 2025 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort This inn offers a relaxing and comfortable stay. The location is centrally located in the heart of Ashland and the accomodations are amazing. We loved the welcome cookies and the breakfast was incredible. The Victorian architecture of the Inn, the gardens, and surrounding cottages were beatiful. There were so many places to sit and enjoy the gardens, food, and drinks. ##### Nick Stayed 1 night in Jul 2025 ### 10/10 Excellent #### Shanna Sep 8, 2025 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Beautiful property. The room was spacious and clean. The sheets were soft and the bed was comfortable. The wait staff was very professional and attentive. The breakfast was delicious and included in the stay. It was walkable to Old Town Ashland. We stayed on foot for most of our stay. Very close to Lithia Park, dining and entertainment. Highly recommend. ##### Shanna Stayed 2 nights in Sep 2025 ### 10/10 Excellent #### Verified traveller Apr 21, 2025 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort Great inn. Maintained beautifully. Excellent service from staff, who make guests very comfortable. ##### Verified traveller Stayed 2 nights in Apr 2025 ### 10/10 Excellent #### Bette Aug 27, 2025 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Beautiful setting with great service and food. Only problem was the bees nest above our patio room. Couldn’t sit outside because of the bees. ##### Bette Stayed 2 nights in Aug 2025 ### 10/10 Excellent #### Kathleen Feb 21, 2025 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Comfortable rooms with many amenities. Their sister restaurant across the street, Chateaubriand, is amazing!!! ##### Kathleen Stayed 1 night in Feb 2025 ### 10/10 Excellent #### Jennifer Oct 15, 2024 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Awesome location and amazing included breakfast. The bed was cozy and Eastlake room was delightful. ##### Jennifer Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### Len May 16, 2025 Liked: Cleanliness, staff & service, amenities, property conditions & facilities quaint room. Fantastic restaurant. Excellent staff. Grounds need some sttention. ##### Len Stayed 2 nights in May 2025 ### 10/10 Excellent #### Paula Oct 2, 2023 Liked: Cleanliness, staff & service, property conditions & facilities This is such a fantastic place to stay in Ashland Oregon. The accommodations are lovely and the on-site restaurant is truly incredible. ##### Paula Stayed 2 nights in Sep 2023 ### 10/10 Excellent #### Baki Oct 24, 2024 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Booked this last minute and was very pleased-very friendly staff, great clean room, very close to restaurants, and a wonderful complimentary real breakfast! I would definitely choose this place again. ##### Baki Stayed 1 night in Oct 2024 ### 10/10 Excellent #### Kevin Jun 25, 2024 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Absolutely wonderful property and outstanding service. ##### Kevin Stayed 1 night in Jun 2024 ### 10/10 Excellent #### Rob Nov 3, 2024 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Winchester Inn is great place to stay in Ashland. The rooms are spacious, well furnished, clean, and comfy. It is close to the theaters and downtown area so you don't have to drive anywhere once you check in. There are a number of breakfast options and the food is excellent. We would definitely stay there again! ##### Rob Stayed 1 night in Nov 2024 ### 10/10 Excellent #### Larry Aug 17, 2024 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Always a great stop on our travels north and south. Great location. Great restaurant. Rooms are great. Staff are very accommodating, highly recommend ##### Larry Stayed 1 night in Aug 2024 ### 10/10 Excellent #### Diana Jan 20, 2025 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Wonderful The Winchester, especially the Hargadine Suite, is the best hotel on the west coast. I love it so much it is a very very uniquely special place. I go to Ashland specifically for the Winchester and their amazing breakfast. ##### Diana Stayed 2 nights in Jan 2025 ### 10/10 Excellent #### Christine Jul 29, 2024 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Incredibly friendly and helpful staff. Gorgeous accommodations and oh so quiet and peaceful. Amazing breakfast! Highly recommend. ##### Christine Stayed 3 nights in Jul 2024 ### 8/10 Good #### Robert May 10, 2024 Liked: Cleanliness, staff & service, amenities A good place to stay. They need to work on some maintenance issues, though. The included breakfasts are magnificent! ##### Robert Stayed 6 nights in Apr 2024 ### 10/10 Excellent #### william Oct 4, 2023 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Great hotel This is an excellent hotel. Large room, immaculate furnishings (room cookies too!) and excellent breakfast, plus it is perfectly located to stroll Ashland. Highly recommended. ##### william Stayed 1 night in Sep 2023 ### 10/10 Excellent #### Bonnie J May 12, 2024 Liked: Cleanliness, staff & service, amenities, property conditions & facilities The service was delightful ##### Bonnie J Stayed 1 night in May 2024 ### 10/10 Excellent #### Jody Jun 22, 2024 Liked: Cleanliness, staff & service, amenities, property conditions & facilities The staff was courteous, helpful, and conversational. Rooms were clean and stylish. ##### Jody Stayed 2 nights in Jun 2024 ### 10/10 Excellent #### Larry Jul 2, 2024 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Staff was excellent! Room is beautiful! Well stocked! Easy access to restaurants! ##### Larry Stayed 1 night in Jul 2024 ### 10/10 Excellent #### Kathryn Jul 29, 2024 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Perfection Room very nice. Great location. Delicious food. ##### Kathryn Stayed 2 nights in Jul 2024 ### 10/10 Excellent #### Monica Jan 14, 2025 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Our stay was great the staff was helpful and on top of everything! Also they have a fabulous restaurant and bar. We enjoyed some evening drinks and if we wanted could take back the drinks to our room. The breakfast was heavenly and the waiter provided top notch service. The room was clean, neat and they proved lovely treats. All in all I will be back. ##### Monica Stayed 2 nights in Jan 2025 ## Expedia's Latest Trends ### Hotels > [Staypineapple, Hotel Rose, Downtown Portland](https://www.expedia.ca/Portland-Hotels-Staypineapple.h440831.Hotel-Information) > > [Hotel Vance, Portland, a Tribute Portfolio Hotel](https://www.expedia.ca/Portland-Hotels-Hotel-Vance.h30039520.Hotel-Information) > > [Hallmark Resort - Cannon Beach](https://www.expedia.ca/Cannon-Beach-Hotels-Hallmark-Resort-Cannon-Beach.h5431022.Hotel-Information) > > [University Place Hotel & Conference Center](https://www.expedia.ca/Portland-Hotels-University-Place-Hotel-Conference-Center.h17920.Hotel-Information) > > [Jupiter Hotel](https://www.expedia.ca/Portland-Hotels-Jupiter-Hotel.h1062725.Hotel-Information) > > [Moxy Portland Downtown](https://www.expedia.ca/Portland-Hotels-Moxy-Portland-Downtown.h61340845.Hotel-Information) > > [The Duniway Portland A Hilton Hotel](https://www.expedia.ca/Portland-Hotels-The-Duniway-Portland-A-Hilton-Hotel.h17395433.Hotel-Information) > > [The Porter Portland, Curio Collection by Hilton](https://www.expedia.ca/Portland-Hotels-The-Porter-Portland.h21728839.Hotel-Information) > > [Hampton Inn & Suites Portland-Pearl District](https://www.expedia.ca/Portland-Hotels-Hampton-Inn-And-Suites-By-Hilton-Portland-Pearl-District.h18754357.Hotel-Information) > > [Heathman Hotel](https://www.expedia.ca/Portland-Hotels-The-Heathman-Hotel.h3096.Hotel-Information) > > [Surfsand Resort](https://www.expedia.ca/Cannon-Beach-Hotels-Surfsand-Resort.h9753263.Hotel-Information) > > [Mark Spencer Hotel](https://www.expedia.ca/Portland-Hotels-Mark-Spencer-Hotel.h19921.Hotel-Information) > > [Hilton Portland Downtown](https://www.expedia.ca/Portland-Hotels-Hilton-Portland-Downtown.h25551.Hotel-Information) > > [The Nines, a Luxury Collection Hotel, Portland](https://www.expedia.ca/Portland-Hotels-The-Nines.h2140707.Hotel-Information) > > [Tolovana Inn](https://www.expedia.ca/Cannon-Beach-Hotels-Tolovana-Inn.h1094927.Hotel-Information) > > [Hyatt Regency Portland at the Oregon Convention Center](https://www.expedia.ca/Portland-Hotels-Hyatt-Regency-Portland-At-The-Oregon-Convention-Center.h39915679.Hotel-Information) > > [Abigail’s Bed & Breakfast Inn](https://www.expedia.ca/Medford-Hotels-Abigails-Bed-Breakfast-Inn.h4966403.Hotel-Information) > > [The Hotel Zags Portland](https://www.expedia.ca/Portland-Hotels-The-Hotel-Zags-Portland.h22135.Hotel-Information) > > [Hyatt House Portland/Downtown](https://www.expedia.ca/Portland-Hotels-Hyatt-House-PortlandDowntown.h15490291.Hotel-Information) > > [Homewood Suites by Hilton Vancouver-Portland](https://www.expedia.ca/Portland-Hotels-Homewood-Suites-By-Hilton-Vancouver-Portland.h62858.Hotel-Information) > > [Crowne Plaza Portland Downtown Convention Center by IHG](https://www.expedia.ca/Portland-Hotels-Crowne-Plaza-Portland-Downtown-Convention-Center.h40665.Hotel-Information) > > [Dossier Hotel](https://www.expedia.ca/Portland-Hotels-Dossier.h285371.Hotel-Information) > > [Courtyard by Marriott Portland City Center](https://www.expedia.ca/Portland-Hotels-Courtyard-By-Marriott-Portland-City-Center.h2469036.Hotel-Information) > > [The Benson Portland, Curio Collection by Hilton](https://www.expedia.ca/Portland-Hotels-The-Benson.h28272.Hotel-Information) > > [Hotel Lucia](https://www.expedia.ca/Portland-Hotels-Hotel-Lucia.h15988.Hotel-Information) > > [Hotel deLuxe](https://www.expedia.ca/Portland-Hotels-Hotel-DeLuxe.h37645.Hotel-Information) > > [The Paramount Hotel](https://www.expedia.ca/Portland-Hotels-The-Paramount-Hotel.h330558.Hotel-Information) > > [Embassy Suites by Hilton Portland Downtown](https://www.expedia.ca/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Downtown.h74615.Hotel-Information) > > [The Royal Sonesta Portland Downtown](https://www.expedia.ca/Portland-Hotels-Royal-Sonesta-Portland.h41174.Hotel-Information)