Title: The 10 Best Hotels Near Windsor Ski Lift, Ashland from CA $86 | Expedia.ca [Ashland Travel Guide](https://expedia.ca/Ashland.dx6290)[Vacation Rentals in Ashland](https://expedia.ca/Ashland-Vacation-Rentals.d6290.Travel-Guide-VacationRentals)[Flights to Ashland](https://expedia.ca/Cheap-Flights-To-Ashland.d6290.Travel-Guide-Flights)[Things to do in Ashland](https://expedia.ca/Things-To-Do-In-Ashland.d6290.Travel-Guide-Activities)[Windsor Ski Lift Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor-Ski-Lift.d553248621556372385.Car-Rental-Guide)[Windsor Ski Lift Vacations](https://expedia.ca/Windsor-Ski-Lift-Ashland.d553248621556372385.Vacation-Attraction) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels near Windsor Ski Lift, Ashland from CA $86 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=553248621556372385&startDate=2025-10-28&endDate=2025-10-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=553248621556372385&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248621556372385&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248621556372385&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Top Hotels Close to Windsor Ski Lift ![Desk, blackout drapes, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/f8004dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/1f352a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/feabb486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/e097575f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flagship Inn of Ashland 11.4 km from Windsor Ski Lift 8.8/10 Excellent (1108) "Easy smooth check in, comfy beds" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Rose CA $77 CA $86 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.Hotel-Information) ![Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/2d34db80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/af89d40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/609741f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | Private kitchen](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/52c43a54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Callahan's Mountain Lodge 8.8 km from Windsor Ski Lift 8.8/10 Excellent (1174) "Loved our visit there, staff was top notch" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $145 CA $169 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/7580c086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/3c8278b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Queen Beds With Kitchen (No Pets Allowed) | Private kitchen](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/10a08da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room, 3 Queen Beds (No Pets Allowed)](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/e32a2cac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Timbers INN and Suites 11.3 km from Windsor Ski Lift 8.6/10 Excellent (1014) "Solid place to stay for the price. Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zackery CA $82 CA $91 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Medford-Hotels-Timbers-Motel.h915968.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/3cd7d8f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/w3456h2065x0y1-0cc9f674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/97525808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/1fd43c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ashland Hills Hotel & Suites 11.8 km from Windsor Ski Lift 9.0/10 Wonderful (1490) "This hotel is an expansive, beautiful propert. I would recommend for any kind of traveler. The hottub was an extra bonus." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosanna CA $133 CA $162 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/7ef065ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/306c76f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Creekside Suite | Living area](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/235e6367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sunrise Suite](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/887e2bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Willows Inn and Estate 10 km from Windsor Ski Lift 9.8/10 Exceptional (33) "Beautiful setting close to downtown. Pool is marvelous!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $230 CA $234 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Ashland-Hotels-Country-Willows-Inn-And-Estate.h89657723.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/2acbb0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen Room, Mountainside | Mountain view](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/4093c3d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/5f7e6be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratford Inn Siskiyou-Hargadine Historic District, 12.1 km from Windsor Ski Lift 9.4/10 Exceptional (1572) "We had a very nice stay! Rooms were comfortable, and the location is great - many great dining choices and entertainment within walking distance of the hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $151 CA $168 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845432/2a6193b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845432/3bf5b42a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/850000/845500/845432/5b2299a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/1000000/850000/845500/845432/fd8dc2cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Ashland by IHG 11.6 km from Windsor Ski Lift 9.2/10 Wonderful (1014) "Nice clean hotel well located for travel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zachary CA $155 CA $173 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Medford-Hotels-Holiday-Inn-Express-Suites-Ashland.h845432.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/e0d19362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/6d4857ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Kitchen | Private kitchen](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/c31d8ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/69e23b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Windsor Inn 11.9 km from Windsor Ski Lift 9.0/10 Wonderful (1003) "Location very convenient, close to I5 and close enough to downtown" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenni CA $137 CA $153 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Medford-Hotels-Best-Western-Windsor-Inn.h2550.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/59ddab0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/c5aa855a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/5e44a7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ashland Springs Hotel Historic Downtown District, 12.4 km from Windsor Ski Lift 9.2/10 Wonderful (1011) "Yummy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) martin CA $146 CA $184 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information) ![Honeymoon Suite #7, 1 Queen Bed, Jetted Tub, Mountain Views](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/965ebb54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/91792c28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/0e643dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/7283f84d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peerless Hotel by WanderLodges Historic Railroad District, 12.6 km from Windsor Ski Lift 9.6/10 Exceptional (90) "A lovely spot to stay! Our room was beautifully furnished and cozy with a historic charm. The outdoor balcony was a great way to wake up with a cup of coffee. Within walking distance of the theaters and downtown. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $162 CA $257 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Ashland-Hotels-The-Peerless-Hotel-By-WanderLodges.h92723926.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/684defd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Barbara Howard)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/815c2dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/a65795fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/30df7c7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winchester Inn Historic Downtown District, 12.3 km from Windsor Ski Lift 9.8/10 Exceptional (256) "Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $218 CA $259 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Medford-Hotels-Winchester-Inn.h1505812.Hotel-Information) ![Standard Room, 1 King Bed (Newly Redone)](https://images.trvl-media.com/lodging/4000000/3630000/3626200/3626125/517414b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/4000000/3630000/3626200/3626125/ee23e57f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/4000000/3630000/3626200/3626125/9014cd0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/4000000/3630000/3626200/3626125/35af3d68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax Inn At Ashland 11.7 km from Windsor Ski Lift 6.8/10 (491) "Easy check in, friendly staff, clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marilynn CA $106 CA $119 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Medford-Hotels-Relax-Inn-At-Ashland.h3626125.Hotel-Information) ![Luxury House, 2 Bedrooms, Bathtub, Garden Area | Private kitchen](https://images.trvl-media.com/lodging/100000000/99050000/99049800/99049787/692adda7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99050000/99049800/99049787/04a800c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury House, 2 Bedrooms, Bathtub, Garden Area | Private kitchen](https://images.trvl-media.com/lodging/100000000/99050000/99049800/99049787/b08d17d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99050000/99049800/99049787/fb57e1a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Barclay Klum House by WanderLodges 12.2 km from Windsor Ski Lift 10/10 Exceptional (6) "Great ~ memorable stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $215 CA $422 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Ashland-Hotels-Barclay-Klum-North-By-WanderLodges.h99049787.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/1000000/890000/880600/880585/7e1c38a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/890000/880600/880585/ce5994ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/890000/880600/880585/3c576aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/890000/880600/880585/3070d1ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Plaza Inn & Suites at Ashland Creek 12.9 km from Windsor Ski Lift 8.8/10 Excellent (1016) "Charming hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) john CA $162 CA $181 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Medford-Hotels-Plaza-Inn-Suites-At-Ashland-Creek.h880585.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/80dea5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/7fe2e00a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/eed498c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/d3116ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bard's Inn, BW Signature Collection by Best Western Historic Downtown District, 12.8 km from Windsor Ski Lift 8.6/10 Excellent (1007) "My favorite place to stay in Ashland. Clean and nice rooms, affordable, PERFECT location and great staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsey CA $138 CA $154 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/102000000/101420000/101411500/101411457/fecb837b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, towels, soap, shampoo](https://images.trvl-media.com/lodging/102000000/101420000/101411500/101411457/a1fd759a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101420000/101411500/101411457/a109cc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Double Room | Shared kitchen](https://images.trvl-media.com/lodging/102000000/101420000/101411500/101411457/fdd64788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ashland Commons Hostel 12.9 km from Windsor Ski Lift 9.4/10 Exceptional (49) "Nice hostel and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) EASWARAMOORTHI CA $36 CA $97 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Ashland-Hotels-Ashland-Commons-Hostel.h101411457.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/24000000/23080000/23072100/23072048/fb75bbea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/24000000/23080000/23072100/23072048/c91b020a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/24000000/23080000/23072100/23072048/e235cb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio, 1 Queen Bed, Kitchen | Private kitchen](https://images.trvl-media.com/lodging/24000000/23080000/23072100/23072048/e8c1558e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palm Cottages 11.6 km from Windsor Ski Lift 9.2/10 Wonderful (210) "Lovely facility. Top notch staff. Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ann CA $241 CA $269 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Medford-Hotels-Palm-Cottages.h23072048.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/47000000/46090000/46085100/46085022/6d9845b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/47000000/46090000/46085100/46085022/4de1acfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/47000000/46090000/46085100/46085022/182a70f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden view](https://images.trvl-media.com/lodging/47000000/46090000/46085100/46085022/87a63cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Arden Forest Inn 13.3 km from Windsor Ski Lift 9.8/10 Exceptional (101) "This was our second visit and always a nice stay during the summer months. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $218 CA $244 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Medford-Hotels-Arden-Forest-Inn.h46085022.Hotel-Information) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/3000000/2050000/2042000/2041971/37ac672b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2050000/2042000/2041971/5d4cb817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2050000/2042000/2041971/d7a15255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/3000000/2050000/2042000/2041971/00991541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cedarwood Inn of Ashland 10.9 km from Windsor Ski Lift 7.4/10 Good (1003) "Room was clean and the customer Service was top notch. Would stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeremiah CA $109 CA $122 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Medford-Hotels-Cedarwood-Inn-Of-Ashland.h2041971.Hotel-Information) ![Main House | Terrace/patio](https://images.trvl-media.com/lodging/96000000/95270000/95265600/95265593/3c6e2bb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Main House | Private kitchen](https://images.trvl-media.com/lodging/96000000/95270000/95265600/95265593/075e9d5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lower Suite | Private kitchen](https://images.trvl-media.com/lodging/96000000/95270000/95265600/95265593/3c235430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95270000/95265600/95265593/30014c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Cowslip's Belle Inn 12.9 km from Windsor Ski Lift 9.8/10 Exceptional (39) "Lovely yard courtyard area with koi pond" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $189 CA $288 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Ashland-Hotels-A-Cowslips-Belle-Inn.h95265593.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-11&endDate=2025-11-12®ionId=553248621556372385&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Top Windsor Ski Lift Hotel Reviews ![Stratford Inn](//images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028_y.jpg) ### Stratford Inn 10/10 Excellent "Staff was very helpful and cheerful. Older property, but well kept up. Very convenient location right in the middle of Ashland. " [](https://expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Ashland Hills Hotel & Suites](//images.trvl-media.com/lodging/1000000/30000/28200/28139/3cd7d8f2_y.jpg) ### Ashland Hills Hotel & Suites 10/10 Excellent "This hotel is an expansive, beautiful propert. I would recommend for any kind of traveler. The hottub was an extra bonus." [](https://expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.Hotel-Information) ![Country Willows Inn and Estate](//images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/7ef065ed_y.jpg) ### Country Willows Inn and Estate 10/10 Excellent "Lisa was very accommodating. Inn has been updated since we were there. Very quiet and comfortable." [](https://expedia.ca/Ashland-Hotels-Country-Willows-Inn-And-Estate.h89657723.Hotel-Information) ![Callahan's Mountain Lodge](//images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/2d34db80_y.jpg) ### Callahan's Mountain Lodge 10/10 Excellent "Love the setting here. The view is great. The staff welcoming and the room perfect. " [](https://expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information) ![Flagship Inn of Ashland](//images.trvl-media.com/lodging/1000000/50000/42900/42817/f8004dc1_y.jpg) ### Flagship Inn of Ashland 10/10 Excellent "Loved the waffles, so happy you provided bananas. It was so quiet and convenient and close to my friend’s hospital. Loved the Mexican restaurant so close to the hotel, and no problems parking. 👍" [](https://expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.Hotel-Information) ![Relax Inn At Ashland](//images.trvl-media.com/lodging/4000000/3630000/3626200/3626125/517414b0_y.jpg) ### Relax Inn At Ashland 10/10 Excellent "Loved loved the staff she was sweet informative and just an all around joy to have done business with highly recommended stay Great place." [](https://expedia.ca/Medford-Hotels-Relax-Inn-At-Ashland.h3626125.Hotel-Information) ![Plaza Inn & Suites at Ashland Creek](//images.trvl-media.com/lodging/1000000/890000/880600/880585/7e1c38a2_y.jpg) ### Plaza Inn & Suites at Ashland Creek 10/10 Excellent "The room was large and clean and air conditioner. Well. Breakfast with some healthy options. The classes is close to downtown. It was very safe." [](https://expedia.ca/Medford-Hotels-Plaza-Inn-Suites-At-Ashland-Creek.h880585.Hotel-Information) ![Best Western Windsor Inn](//images.trvl-media.com/lodging/1000000/10000/2600/2550/e0d19362_y.jpg) ### Best Western Windsor Inn 10/10 Excellent "We really appreciated the free EV charger. It was a faster slow charger. " [](https://expedia.ca/Medford-Hotels-Best-Western-Windsor-Inn.h2550.Hotel-Information) ![Holiday Inn Express & Suites Ashland by IHG](//images.trvl-media.com/lodging/1000000/850000/845500/845432/2a6193b5_y.jpg) ### Holiday Inn Express & Suites Ashland by IHG 10/10 Excellent "Great stay! The hotel was very clean and pretty quiet considering there were quite a few guests there. Rooms were nice and big, great amenities and convenient location." [](https://expedia.ca/Medford-Hotels-Holiday-Inn-Express-Suites-Ashland.h845432.Hotel-Information) ## Hotels near other Windsor Ski Lift attractions [](https://www.expedia.ca/Mount-Ashland-Ski-Area-Hotels.0-l6087455-0.Travel-Guide-Filter-Hotels) ### Mount Ashland Ski Area 4.2/5 (136 reviews) Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and entertainment choices in this walkable area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6087455) [](https://www.expedia.ca/Comer-Ski-Lift-Hotels.0-l553248621556372384-0.Travel-Guide-Filter-Hotels) ### Comer Ski Lift You can take time to visit Comer Ski Lift during your travels to Ashland. Discover the top-notch restaurants and lively festivals in this walkable area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621556372384) [](https://www.expedia.ca/Ariel-Ski-Lift-Hotels.0-l553248621556372386-0.Travel-Guide-Filter-Hotels) ### Ariel Ski Lift You can take time to visit Ariel Ski Lift during your travels to Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621556372386) [](https://www.expedia.ca/Bull-Gap-Lower-Trailhead-Hotels.0-l553248635976800844-0.Travel-Guide-Filter-Hotels) ### Bull Gap Lower Trailhead 3.0/5 (1 review) You can take time to visit Bull Gap Lower Trailhead during your travels to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635976800844) [](https://www.expedia.ca/Lithia-Artisans-Market-Hotels.0-l553248621533114062-0.Travel-Guide-Filter-Hotels) ### Lithia Artisans Market You can find out about the history of Ashland with a trip to Lithia Artisans Market. Experience the entertainment choices and lively festivals in this walkable area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621533114062) [](https://www.expedia.ca/Tashi-Choling-Buddhist-Center-Hotels.0-l553248635976800843-0.Travel-Guide-Filter-Hotels) ### Tashi Choling Buddhist Center 4.0/5 (1 review) Find out about the history of Ashland when you take a trip to Tashi Choling Buddhist Center. Wander around the area's picturesque gardens or experience its acclaimed theater scene. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635976800843) [](https://www.expedia.ca/Weisinger-Family-Winery-Hotels.0-l873860607758278656-0.Travel-Guide-Filter-Hotels) ### Weisinger Family Winery You can enjoy a tasting or tour at Weisinger Family Winery during your travels to Ashland. Wander around the area's picturesque gardens or experience its lively festivals. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=873860607758278656) [](https://www.expedia.ca/Emigrant-Lake-Hotels.0-l553248621558078461-0.Travel-Guide-Filter-Hotels) ### Emigrant Lake 4.1/5 (35 reviews) Commune with nature and explore the great outdoors at Emigrant Lake during your travels in Ashland. Experience the lively festivals and entertainment choices in this family-friendly area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621558078461) ## Frequently asked questions ### What's the area like around Windsor Ski Lift? > Windsor Ski Lift is located in a family-friendly area of Ashland known for its picturesque gardens and array of dining options. Ashland is home to 312 hotels and other accommodations, so you can find something that's perfect for your stay. ### Where is the best place to stay near Windsor Ski Lift? > [Flagship Inn of Ashland](https://www.expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.Hotel-Information) is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and a restaurant. You'll find it 7.1 mi (11.4 km) from Windsor Ski Lift. Other good choices in the area include [Ashland Hills Hotel & Suites](https://www.expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.Hotel-Information) and [Callahan's Mountain Lodge](https://www.expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information). ### If I need to cancel the hotel reservation for my stay near Windsor Ski Lift, will I receive a refund? > Yes, most hotel bookings are fully refundable as long as you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then you can use the "fully refundable" filter to get the top deals on offer near Windsor Ski Lift. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [3 Star Hotels in Ashland](https://www.expedia.ca/3Star-Ashland-Hotels.s30-0-d6290.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Ashland](https://www.expedia.ca/5Star-Ashland-Hotels.s50-0-d6290.Travel-Guide-Filter-Hotels) - [Hotels near Allen Elizabethan Theatre](https://www.expedia.ca/Allen-Elizabethan-Theatre-Hotels.0-l6078449-0.Travel-Guide-Filter-Hotels) - [Hotels near Asante Rogue Regional Medical Center](https://www.expedia.ca/Asante-Rogue-Regional-Medical-Center-Hotels.0-l6216738-0.Travel-Guide-Filter-Hotels) - [Apartments in Ashland](https://www.expedia.ca/Ashland-Apartments.d6290-aaApartments.Travel-Guide-Accommodation) - [B&B in Ashland](https://www.expedia.ca/Ashland-Bed-And-Breakfast.d6290-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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[Flights from Toronto (YYZ) to Ashland (AHM)](https://www.expedia.ca/lp/flights/yyz/ahm/toronto-to-ashland) - [Ashland Vacations](https://www.expedia.ca/Ashland.d6290.Destination-Travel-Guides) - [Visit Ashland](https://www.expedia.ca/Ashland.dx6290) - [Thomas Theatre](https://www.expedia.ca/Thomas-Theatre-Historic-Downtown-District.d6078459.Vacation-Attraction) - [Avis Rental Cars in Ashland](https://www.expedia.ca/Avis-Car-Rentals-In-Ashland.d6290-c41.Car-Rental-Guide-Suppliers) - [Car rental Ashland](https://www.expedia.ca/Car-Rentals-In-Ashland.d6290.Car-Rental-Guide) - [Enterprise Rental Cars in Ashland](https://www.expedia.ca/Enterprise-Car-Rentals-In-Ashland.d6290-c15.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in Ashland](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Ashland.d6290-c45.Car-Rental-Guide-Suppliers) - [Ashland Vacation Rentals](https://www.expedia.ca/Ashland-Vacation-Rentals.d6290.Travel-Guide-VacationRentals) - [Things to do in Ashland](https://www.expedia.ca/Things-To-Do-In-Ashland.d6290.Travel-Guide-Activities)