Title: Top Chalets in Windsor County in 2026 | Expedia.ca [Windsor County Hotels](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Hotel-Destinations)[Vacation Rentals in Windsor County](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Vacation-Rental-Destinations)[Windsor County Car Rentals](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Car-Rental-Destinations)[Windsor County Vacations](https://expedia.ca/Windsor-County.d553248635976432508.Destination-Travel-Guides) ![Must stop while in Vermont #autumn #fall #roadtrip #travel #adventure #colorful #vermont ](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rachel Samanyi ![](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Windsor County ![Ludlow showing street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94298-Ludlow.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Ludlow [](https://expedia.ca/Ludlow-Chalets.d8496-aaChalets.Travel-Guide-Accommodation) ![Woodstock featuring a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94311-Woodstock.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Woodstock [](https://expedia.ca/Woodstock-Chalets.d10868-aaChalets.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/212ecbf3b606238229538e223f3f57eb.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### White River Junction [](https://expedia.ca/White-River-Junction-Chalets.d6294-aaChalets.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.ca/Windsor-Chalets.d7881-aaChalets.Travel-Guide-Accommodation) ![Quechee featuring a river or creek, a bridge and tranquil scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93816-Central-Vermont.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Quechee [](https://expedia.ca/Quechee-Chalets.d9580-aaChalets.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/6e1ce19989493034a8e8934b004054dd.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Norwich [](https://expedia.ca/Norwich-Chalets.d184063-aaChalets.Travel-Guide-Accommodation) ## Our top choices for Windsor County chalets ![Exterior](https://images.trvl-media.com/lodging/71000000/70970000/70966100/70966049/4d9690a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books, computer monitors](https://images.trvl-media.com/lodging/71000000/70970000/70966100/70966049/59944392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books, computer monitors](https://images.trvl-media.com/lodging/71000000/70970000/70966100/70966049/6f572bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books, computer monitors](https://images.trvl-media.com/lodging/71000000/70970000/70966100/70966049/16b21755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt. [](https://www.expedia.ca/Plymouth-Hotels-Black-Dog-Lodge-Secluded-Chalet.h70966049.Hotel-Information) Plymouth 9.8/10 Exceptional (26 reviews) "Great pet friendly property perfectly located between Woodstock and Killington. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Norman Y. [](https://www.expedia.ca/Plymouth-Hotels-Black-Dog-Lodge-Secluded-Chalet.h70966049.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/3ae797cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/7245eec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/ffdad819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/bbf460e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails [](https://www.expedia.ca/Ludlow-Hotels-Delightful-Ski-Chalet-Minutes-To-Okemo.h71643979.Hotel-Information) Ludlow 10/10 Exceptional (42 reviews) "This was our 2nd year in a row staying at Noreen’s place. The property is breathtaking, the house is well appointed with comfy beds, solid WiFi and a great kitchen. We had 6 adults and 7 kids and the space never felt cramped, but for us the real show stopper is the side yard and deck. Awesome views, one of the best fire pits I have ever seen and a lawn worthy of many kids games. Extra bonus this year was clear weather to see the Presides meteor shower at night. We can’t wait to stay again next... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip C. [](https://www.expedia.ca/Ludlow-Hotels-Delightful-Ski-Chalet-Minutes-To-Okemo.h71643979.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/d8d782e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/fa3b4847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/b0e20853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/21b6d816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Creekside Chalet centrally located near 4 ski resorts [](https://www.expedia.ca/Weston-Hotels-Cozy-Creekside-Chalet-Centrally-Located-Near-4-Ski-Resorts.h83534431.Hotel-Information) Weston 10/10 Exceptional (16 reviews) "An attractive home in a nice area. The hosts are very kind people and very accommodating. I would stay again. The location is convenient to many interesting places. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ed C. [](https://www.expedia.ca/Weston-Hotels-Cozy-Creekside-Chalet-Centrally-Located-Near-4-Ski-Resorts.h83534431.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/25573866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/e1cc1c95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, Hulu](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/75c61d5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, Hulu](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/ab183130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base! [](https://www.expedia.ca/Ludlow-Hotels-Gorgeous-Ski-Chalet-With-Game-Room-Hot-Tub-On-Okemo-Mt-Under-1-Mile-To-Base.h33503516.Hotel-Information) Ludlow 9.8/10 Exceptional (129 reviews) "Spacious, clean, beautiful property, well-stocked, host extremely responsive " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa D. [](https://www.expedia.ca/Ludlow-Hotels-Gorgeous-Ski-Chalet-With-Game-Room-Hot-Tub-On-Okemo-Mt-Under-1-Mile-To-Base.h33503516.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/398175e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/40bc0fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/13b3aaae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/97cdf1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 4bd - Ski Okemo, Killington, Magic & Bromley [](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.Hotel-Information) Chester 10/10 Exceptional (10 reviews) "We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carla C. CA $443 CA $829 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/df814428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, stereo](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/991631e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/0ffa08bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, stereo](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/b1d619f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Okemo Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village [](https://www.expedia.ca/Ludlow-Hotels-DISCOUNTED-RATES-AVAILABLE-10-To-15-Off-For-3-Or-More-Days-Booked.h33735418.Hotel-Information) Ludlow 9.4/10 Exceptional (24 reviews) "We were up for a weekend in February. Perfect place. Plenty of beds. The hot tub was a bonus. Excellent communication by the hosts. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom G. [](https://www.expedia.ca/Ludlow-Hotels-DISCOUNTED-RATES-AVAILABLE-10-To-15-Off-For-3-Or-More-Days-Booked.h33735418.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/83000000/82840000/82835500/82835471/629f7098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82840000/82835500/82835471/8cb2c6ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/83000000/82840000/82835500/82835471/807f004b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/83000000/82840000/82835500/82835471/7933ad01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults [](https://www.expedia.ca/Ludlow-Hotels-Ski-Inout-Chalet-On-Okemos-Sachem-Trail-Sleeps-22-Adults.h82835471.Hotel-Information) ludlow 10/10 Exceptional (30 reviews) "Our stay was great! House was excellent, location was perfect, and Dave was super accommodating!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna B. [](https://www.expedia.ca/Ludlow-Hotels-Ski-Inout-Chalet-On-Okemos-Sachem-Trail-Sleeps-22-Adults.h82835471.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39650000/39649600/39649525/d6a58c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/40000000/39650000/39649600/39649525/b0740d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39650000/39649600/39649525/2c39def6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39650000/39649600/39649525/6621ee37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski [](https://www.expedia.ca/Woodstock-Hotels-Woodbridge-Inn-6BR-Historic-CharmRiverfrontHot-TubClose-To-Ski.h39649525.Hotel-Information) Woodstock 10/10 Exceptional (27 reviews) "Great space for large family gathering! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ted d. [](https://www.expedia.ca/Woodstock-Hotels-Woodbridge-Inn-6BR-Historic-CharmRiverfrontHot-TubClose-To-Ski.h39649525.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/c0ffd596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/2d38a4a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/83d70fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/1e794e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Okemo Mountain Chalet W/ Hot Tub and Game Room [](https://www.expedia.ca/Ludlow-Hotels-Okemo-Mountain-Chalet-W-Hot-Tub-And-Game-Room.h23927486.Hotel-Information) Ludlow 9.8/10 Exceptional (161 reviews) "Perfect for our multi-generational family get together!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael B. [](https://www.expedia.ca/Ludlow-Hotels-Okemo-Mountain-Chalet-W-Hot-Tub-And-Game-Room.h23927486.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/63238a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/0df9f82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/ad2f042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/0c516aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington [](https://www.expedia.ca/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information) Plymouth 10/10 Exceptional (14 reviews) "We had a great stay! Beautiful spot tucked in the woods. Great host communication!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie-Anne B. CA $416 CA $978 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/31000000/30400000/30397900/30397853/3264bc4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/31000000/30400000/30397900/30397853/e4a6dee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/31000000/30400000/30397900/30397853/be76101e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/31000000/30400000/30397900/30397853/74677f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4 [](https://www.expedia.ca/Stockbridge-Hotels-Cozy.h30397853.Hotel-Information) Stockbridge 9.6/10 Exceptional (52 reviews) "Beautiful property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sheri n. [](https://www.expedia.ca/Stockbridge-Hotels-Cozy.h30397853.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74010000/74006000/74005987/63e2a250.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74010000/74006000/74005987/8e1db3eb_edited_b986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74010000/74006000/74005987/571f7854_edited_7762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, WiFi](https://images.trvl-media.com/lodging/75000000/74010000/74006000/74005987/9b2960b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo [](https://www.expedia.ca/Ludlow-Hotels-Modern-7Bd3Ba-Mountain-Chalet-W-Hot-Tub.h74005987.Hotel-Information) Ludlow 10/10 Exceptional (10 reviews) "Great house, made our ski weekend easy and fun. House is better than the pictures." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Trevor D. [](https://www.expedia.ca/Ludlow-Hotels-Modern-7Bd3Ba-Mountain-Chalet-W-Hot-Tub.h74005987.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/8f93d503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/eb09d128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/b3403a6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/87f6cc90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village [](https://www.expedia.ca/Woodstock-Hotels-Falcon-House-VT-Modern-Chalet-WSauna-On-60-Acres-Hiking-Bike-To-Village.h20178157.Hotel-Information) West Woodstock 10/10 Exceptional (72 reviews) "The house was very clean and tidy. Kat was great at communicating and making sure we had everything we needed!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin P. [](https://www.expedia.ca/Woodstock-Hotels-Falcon-House-VT-Modern-Chalet-WSauna-On-60-Acres-Hiking-Bike-To-Village.h20178157.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/48be0320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/b2a8b57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/c33b35a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/98a04e79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gnome Home Mountain Ski Chalet w/Sauna Killington [](https://www.expedia.ca/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information) Stockbridge 10/10 Exceptional (4 reviews) "Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald S. CA $389 CA $792 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/65000000/64590000/64587700/64587644/8dcca8f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/65000000/64590000/64587700/64587644/45736a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64590000/64587700/64587644/deec2e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/65000000/64590000/64587700/64587644/w451h683x286y0-267606a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow [](https://www.expedia.ca/Cavendish-Hotels-Cozy-Mountain-View-Chalet-Near-Okemo.h64587644.Hotel-Information) Cavendish 10/10 Exceptional (15 reviews) "We had a fantastic stay at the Honeycomb Hideout. The house is very well maintained and has everything you need. The weather didn't hold out for us but having a great place to stay made up for it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael K. [](https://www.expedia.ca/Cavendish-Hotels-Cozy-Mountain-View-Chalet-Near-Okemo.h64587644.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/c8c80513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/7516e9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/ed872576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/1eda37b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain [](https://www.expedia.ca/Chester-Hotels-Modern-Chalet-With-Serene-Views-15-Minutes-To-Okemo-Mountain.h93497853.Hotel-Information) Chester 9.2/10 Wonderful (5 reviews) "My husband and I were looking for a quiet place to spend a weekend and Jake and Hannah’s place was perfect! We were close to restaurants, farmers market, arts and crafts fair! The house was clean, had everything we needed. The jacuzzi and the fire pit were perfect for the cool nights. Check in was easy, and Jake and Hannah were prompt to answer any questions. We would love stay again! Thank you for sharing your house! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristina P. [](https://www.expedia.ca/Chester-Hotels-Modern-Chalet-With-Serene-Views-15-Minutes-To-Okemo-Mountain.h93497853.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109560000/109551000/109550902/w3072h2045x0y1-d19d2a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109560000/109551000/109550902/w3071h2045x1y1-054ee8e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109560000/109551000/109550902/8b18e3cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109560000/109551000/109550902/w3072h2045x0y1-72e8894b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom chalet with AC and WiFi in charming Chester [](https://www.expedia.ca/Chester-Hotels-Spacious-5-Bedroom-Chalet-With-AC-And-WiFi-In-Charming-Chester.h109550902.Hotel-Information) Chester 10/10 Exceptional (8 reviews) "This is an amazing property to stay at and has all the amenities one could ask for. We have stayed here twice and will be back. The owner is very helpful and accommodating and communicates well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles B. [](https://www.expedia.ca/Chester-Hotels-Spacious-5-Bedroom-Chalet-With-AC-And-WiFi-In-Charming-Chester.h109550902.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/c2223ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/f3706d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/ba7c3471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/59a6d7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Views. Hot Tub. , 5 Wooded Acres. Private Pond [](https://www.expedia.ca/Plymouth-Hotels-New-Construction-Post-And-Beam.h115079418.Hotel-Information) Plymouth [](https://www.expedia.ca/Plymouth-Hotels-New-Construction-Post-And-Beam.h115079418.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/45000000/44920000/44910100/44910019/4f669d5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet | In-room dining](https://images.trvl-media.com/lodging/45000000/44920000/44910100/44910019/dce584d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet | Living room](https://images.trvl-media.com/lodging/45000000/44920000/44910100/44910019/3b878475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet | Private kitchen](https://images.trvl-media.com/lodging/45000000/44920000/44910100/44910019/d630ac73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bent Tree [](https://www.expedia.ca/Stockbridge-Hotels-Bent-Tree.h44910019.Hotel-Information) Stockbridge [](https://www.expedia.ca/Stockbridge-Hotels-Bent-Tree.h44910019.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=2026-01-27&endDate=2026-01-28®ionId=553248635976432508&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-County-Chalets.d553248635976432508-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-County-Chalets.d553248635976432508-aaChalets.Travel-Guide-Accommodation) ## Top Windsor County Hotel Reviews ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "All of the above - great little spot!!" [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Clean, nice pool and hot tub, and good price!" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Hotel Coolidge](https://images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "Cute with lots of personality " [](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information) ![COHO Inn & Motor Lodge](https://images.trvl-media.com/lodging/105000000/104400000/104395800/104395732/3f7fd5fb_y.jpg) ### COHO Inn & Motor Lodge 10/10 Excellent "The new owners are so sweet! I would absolutely book again! " [](https://expedia.ca/Weston-Hotels-The-Colonial-House-Inn-And-Motor-Lodge.h104395732.Hotel-Information) ![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Beautiful, quiet inn. We stayed Saturday through Tuesday after the holidyas, so it was especially quiet, just what we wanted. Staff was incredibly attentive and engaging, rooms were unique and comfortable. I highly recommend The Jackson. We will be returning in the spring to see the grounds!" [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Fullerton Inn](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab_y.jpg) ### Fullerton Inn 10/10 Excellent "Where to start!? If you like small town vibe with all the necessities close by I highly suggest this location. The building is absolutely gorgeous and is located on a little “service road” with a few shops and stores in easy walking distance. From front desk to restaurant staff, everyone was fun, helpful, kind and informative. Robert at the front desk was super kind and helpful upon arriving and great to chat with when we stopped for dinner at the tavern later at night, as well as the bar and restaurant/inn staff. This location has a very “home town” vibe which I personally love. And also lots of antiques,vintage items and history still displayed but done RIGHT, to where it feels classy not outdated. We are a snowboarding couple and had plenty of near by adventures we were able to sneak in in between riding and we didn’t lose any time on the mountain. Bathrooms had plenty of hot water and great water pressure. The room we stayed in was spacious, comfortable and clean. We were coming back to the same mountain in a few weeks and although we like checking out different areas we decided to book the next stay before we even left! See you in a few weeks! R and E " [](https://expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) ![Best Western Springfield Hotel](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/f0e2c480_y.jpg) ### Best Western Springfield Hotel 10/10 Excellent "They allowed us to check in early- with no fee. Staff was so kind and quick thinking when we got there. Our toddler stated she needed to use the restroom and the woman at the front desk gave my husband a key to the bathroom ASAP- even before we checked in. Hotel was clean- EVERYWHERE!! Very happy with the complementary breakfast also! Staff was constantly moving to make sure it was fully stocked at all times! We will be back! " [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![The Quechee Inn at Marshland Farm](https://images.trvl-media.com/lodging/2000000/1930000/1924800/1924710/c8372335_y.jpg) ### The Quechee Inn at Marshland Farm 10/10 Excellent "Excellent staff. Had dinner there as well. Very well prepared and was extremely flavorful. Highly recommend. Complimentary breakfast was a plus." [](https://expedia.ca/Quechee-Hotels-The-Quechee-Inn-At-Marshland-Farm.h1924710.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Wonderful stay at this beautiful inn. Couldn’t fault it. The only downside is that the bar and restaurant isn’t open every evening. When it was open, it was excellent - top quality food and brilliant staff." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ## Find out more about Windsor County ## Windsor County Chalets information | Number of reviews | 549 | | ----------------- | ---------- | | Accommodation | 23 Chalets | | Lowest Price | CA $792 | | Highest Price | CA $978 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Billings Farm and Museum ](https://www.expedia.ca/Billings-Farm-And-Museum-Hotels.0-l6175222-0.Travel-Guide-Filter-Hotels) - [Farmstay in Bridgewater ](https://www.expedia.ca/Bridgewater-Agritourism.d553248635975851833-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Bridgewater ](https://www.expedia.ca/Bridgewater-Bed-And-Breakfast.d553248635975851833-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Bridgewater ](https://www.expedia.ca/Bridgewater-Guest-Houses.d553248635975851833-aaGuestHouses.Travel-Guide-Accommodation) - 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