[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) # Winchester Inn Victorian inn with free breakfast and a restaurant ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/684defd4.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Suite, 1 King Bed (Barbara Howard)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/815c2dcc.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Suite, 1 Bedroom (Silverdale) | Living area](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/a170cf24.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/a65795fb.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area](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. 9.8 Exceptional ## Popular amenities - - - Bar - Housekeeping - Laundry - Air conditioning ## Room options ### Check availability for these dates Tonight [Oct. 2 - Oct. 3](https://www.expedia.ca/Hotel-Search?startDate=2025-10-02&endDate=2025-10-03&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-02&endDate=2025-10-03&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) Tomorrow [Oct. 3 - Oct. 4](https://www.expedia.ca/Hotel-Search?startDate=2025-10-03&endDate=2025-10-04&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-03&endDate=2025-10-04&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) This weekend [Oct. 3 - Oct. 5](https://www.expedia.ca/Hotel-Search?startDate=2025-10-03&endDate=2025-10-05&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-03&endDate=2025-10-05&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) Next weekend [Oct. 10 - Oct. 12](https://www.expedia.ca/Hotel-Search?startDate=2025-10-10&endDate=2025-10-12&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-10&endDate=2025-10-12&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) All rooms 1 bed 2 beds 3+ beds Showing 20 of 20 rooms ![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 Separate bedroom - 350 sq ft - 1 bedroom - Sleeps 2 - 1 Queen Bed ![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 Sofa bed - 350 sq ft - 1 bedroom - Sleeps 2 - 1 Queen Bed and 1 Double Sofa Bed ![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 Fan - 350 sq ft - Sleeps 2 - 1 Queen Bed and 1 Twin Bed ![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 ![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 Fan - 350 sq ft - Sleeps 2 - 1 Queen Bed ![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 Fan - 300 sq ft - Sleeps 2 - 1 Queen Bed ![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 ![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 ![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 ![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 Fan - 350 sq ft - Sleeps 2 - 1 King Bed ![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 Fan - 400 sq ft - Sleeps 2 - 1 King Bed ![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 ![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 ![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 ![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 ![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 ![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 ![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 ![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 ![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. More rewards for more adventures! [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 Located in Historic Downtown District, a neighborhood in Ashland, Winchester Inn is in a shopping district. Weisinger Family Winery and Grizzly Peak Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore North Mountain Park and Cascade-Siskiyou National Monument. ScienceWorks Hands-On Museum and The RRRink are also worth visiting. [Visit our Ashland travel guide](https://www.expedia.ca/Ashland.dx6290) [View more Inns in Ashland](https://www.expedia.ca/Ashland-Inns.d6290-aaInns.Travel-Guide-Accommodation) ![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 - Oregon Shakespeare Festival - 3 min walk - 0.3 km - Lithia Park - 3 min walk - 0.3 km - Southern Oregon University - 17 min walk - 1.4 km ### Getting around - Rogue Valley Intl. Airport (MFR) - 22 min drive ### Restaurants - ‪Ruby's - ‬6 min walk - ‪Martolli's Hand Tossed Pizza - ‬5 min walk - ‪RedZone Sports Bar N' Grill - ‬1 min walk - ‪The Growler Guys - ‬3 min walk - ‪Blue Toba - ‬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 - A gift shop, smoke-free premises, and luggage storage - Tour/ticket assistance, 1 meeting room, and concierge services - 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 ![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 1,000 reviews CA $244 CA $278 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=660933&PinnedHotelID=660933&HadPinnedHotel=true®ionId=-1&adults=2) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/80dea5e6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Bard's Inn, BW Signature Collection by Best Western Historic Downtown District - Pool - Breakfast included - Pet-friendly - Parking included 8.8 Excellent 1,023 reviews CA $152 CA $169 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-01&endDate=2025-11-02&selected=9249&PinnedHotelID=9249&HadPinnedHotel=true®ionId=-1&adults=2) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/3cd7d8f2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Ashland Hills Hotel & Suites Ashland - Pool - Hot tub - Spa - Pet-friendly 9.0 Wonderful 1,463 reviews CA $152 CA $183 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-06&endDate=2025-10-07&selected=28139&PinnedHotelID=28139&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor dining](https://images.trvl-media.com/lodging/1000000/890000/880600/880585/7e1c38a2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Plaza Inn & Suites at Ashland Creek Ashland - Breakfast included - Pet-friendly - Parking included - Free WiFi 8.6 Excellent 1,027 reviews CA $174 CA $194 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=880585&PinnedHotelID=880585&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Stratford Inn Siskiyou-Hargadine Historic District - Pool - Hot tub - Pet-friendly - Kids pool 9.4 Exceptional 1,553 reviews CA $117 CA $131 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=2758881&PinnedHotelID=2758881&HadPinnedHotel=true®ionId=-1&adults=2) ![Front of property](https://images.trvl-media.com/lodging/1000000/900000/893600/893586/a941912b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Lithia Springs Resort Ashland - Pool - Hot tub - Spa - Parking included 9.4 Exceptional 1,014 reviews CA $207 CA $231 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=893586&PinnedHotelID=893586&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/e0d19362.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Best Western Windsor Inn Ashland - Pool - Hot tub - Breakfast included - Pet-friendly 9.0 Wonderful 1,001 reviews CA $137 CA $152 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-26&endDate=2025-10-27&selected=2550&PinnedHotelID=2550&HadPinnedHotel=true®ionId=-1&adults=2) ![Desk, blackout drapes, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/f8004dc1.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Flagship Inn of Ashland Ashland - Pool - Breakfast included - Parking included - Free WiFi 8.8 Excellent 1,064 reviews CA $80 CA $90 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=42817&PinnedHotelID=42817&HadPinnedHotel=true®ionId=-1&adults=2) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/24000000/23080000/23072100/23072048/fb75bbea.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Palm Cottages Ashland - Pool - Parking included - Free WiFi - Air conditioning 9.2 Wonderful 209 reviews CA $333 CA $371 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-05&endDate=2025-10-06&selected=23072048&PinnedHotelID=23072048&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/9eb7c716.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Comfort Inn & Suites Ashland Ashland - Pool - Hot tub - Breakfast included - Pet-friendly 8.6 Excellent 1,003 reviews CA $126 CA $128 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=3448&PinnedHotelID=3448&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 ### 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 ### 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? > No, pets are not allowed at this property. ### How much does it cost to stay at Winchester Inn? > As of Oct 2, 2025, prices found for a 1-night stay for 2 adults at Winchester Inn on Oct 27, 2025 start from CA $256.49, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. [Choose your dates](https://www.expedia.ca/Medford-Hotels-Winchester-Inn.h1505812.Hotel-Information?rfrr=HOT.HIS.question.link.click) for more accurate prices. ### How much is parking at Winchester Inn? > Self parking is free at this property. ### What time is check-in at Winchester Inn? > Check-in start time: 4:00 PM; Check-in end time: 9 PM. Late check-in is available during limited hours. ### What time is check-out at Winchester Inn? > Check-out is at 11 AM. Late check-out is available for a fee. ### Where is Winchester Inn located? > Located in Historic Downtown District, this inn is within a 5-minute walk of Oregon Cabaret Theatre, Ashland Library, and Lithia Park. Oregon Shakespeare Festival and Thomas Theatre are also within 5 minutes. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Expedia's Latest Trends ### Hotels > [Comfort Inn & Suites Vancouver Downtown City Center](https://www.expedia.ca/Portland-Hotels-Comfort-Inn-Suites-Vancouver-Downtown-City-Center.h5083.Hotel-Information) > > [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)