Title: Winchester Inn Reviews, Deals & Photos 2025 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) # Winchester Inn Victorian inn with free breakfast and restaurant ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/684defd4.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/30df7c7a.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 King Bed (Barbara Howard) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/815c2dcc.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Suite, 1 Bedroom (Silverdale) | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/a170cf24.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 £162 includes taxes & fees 3 Nov - 4 Nov ## Room options ### Check availability for these dates Tonight [Nov 2 - Nov 3](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) Tomorrow [Nov 3 - Nov 4](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) This weekend [Nov 7 - Nov 9](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-07&endDate=2025-11-09&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-07&endDate=2025-11-09&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) Next weekend [Nov 14 - Nov 16](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-14&endDate=2025-11-16&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-14&endDate=2025-11-16&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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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 Single Bed ![Double Room, 1 Queen Bed (Patio) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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 Single Murphy Bed ![Suite, 1 Queen Bed with Sofa bed (Brighton) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](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.co.uk/login?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMedford-Hotels-Winchester-Inn.h1505812.Hotel-Information)[Sign up, it's free](https://www.expedia.co.uk/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 miles - Allen Elizabethan Theatre - 3 min walk - 0.2 miles - Oregon Shakespeare Festival - 3 min walk - 0.2 miles - Lithia Park - 3 min walk - 0.2 miles - Southern Oregon University - 17 min walk - 0.9 miles #### Getting around - Medford, OR (MFR-Rogue Valley Intl.) - 22 min drive #### Restaurants - ‪Martolli's Hand Tossed Pizza - ‬5 min walk - ‪Ruby's - ‬6 min walk - ‪The Growler Guys - ‬3 min walk - ‪Taqueria Picaro - ‬4 min walk - ‪RedZone Sports Bar N' Grill - ‬1 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 such as: - Free self-parking - A gift shop, smoke-free property and luggage storage - Tour/ticket information, 1 meeting room and concierge services - Guest reviews speak highly of the helpful staff Room features All rooms are individually furnished, and include comforts such as premium bedding and air conditioning, in addition to thoughtful touches such as free WiFi and bathrobes. More conveniences in all rooms include: - Heating and fans - Hypo-allergenic bedding, Egyptian cotton sheets and pillowtop mattresses - Designer toiletries and hairdryers - Flat-screen TVs with cable channels - Wardrobes/cupboards, 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 1,011 reviews £102 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&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 - 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Pool - Breakfast included - Parking included - Free WiFi 8.8 Excellent 1,126 reviews £45 includes taxes & fees 5 Nov - 6 Nov [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-05&endDate=2025-11-06&selected=42817&PinnedHotelID=42817&HadPinnedHotel=true®ionId=-1&adults=2) ![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 573 reviews £154 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=15153095&PinnedHotelID=15153095&HadPinnedHotel=true®ionId=-1&adults=2) ![Free daily full breakfast ](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/7ef065ed.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Country Willows Inn and Estate Ashland - Pool - Breakfast included - Spa - Parking included 9.8 Exceptional 33 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=89657723&PinnedHotelID=89657723&HadPinnedHotel=true®ionId=-1&adults=2) ## Property amenities ### Internet - Available in all rooms: Free WiFi - Available in some public areas: Free WiFi ### Parking and transport - Free self parking on site ### Food and drink - Free cooked-to-order breakfast available daily 8 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 lift - Wheelchair accessible (may have limitations) ### More - 3 floors - 5 buildings - Built in 1886 - Smoke-free property - Victorian architecture ## Room amenities ### Bedroom - Down comforter - Egyptian cotton sheets - Hypo-allergenic bedding - Pillowtop mattress ### Bathroom - Designer toiletries - Dressing gowns - 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 Cots (infant beds) are not available ### Payment types at the property ## 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 per cent 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 This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal. ### We should mention This property does not have any lifts 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 2 Nov 2025, prices found for a 1-night stay for 2 adults at Winchester Inn on 3 Nov 2025 start from £162.41, including 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.co.uk/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? > Checkout is at 11 AM. Late checkout 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. 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