Title: Top Chalets in Windham County in 2026 | Expedia.ca [Windham County Hotels](https://expedia.ca/Destinations-In-Windham-County.d6057353.Hotel-Destinations)[Vacation Rentals in Windham County](https://expedia.ca/Destinations-In-Windham-County.d6057353.Vacation-Rental-Destinations)[Things to do in Windham County](https://expedia.ca/Things-To-Do-In-Windham-County.d6057353.Travel-Guide-Activities)[Windham County Car Rentals](https://expedia.ca/Destinations-In-Windham-County.d6057353.Car-Rental-Destinations)[Windham County Vacations](https://expedia.ca/Windham-County.d6057353.Destination-Travel-Guides) ![New England is known for their covered bridges. A beautiful example is the West Dummerston Bridge over the West River in southern Vermont. #InStone](https://images.trvl-media.com/place/6057353/bdb3e72e-fca5-4208-a6a4-c09318f6a7f8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Bruce Altobelli ![](https://images.trvl-media.com/place/6057353/bdb3e72e-fca5-4208-a6a4-c09318f6a7f8.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 In two weeks [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Windham County ![Autumn at Jones Pond - Carrabassett Valley - Maine - Bigelow Preserve Peak](https://images.trvl-media.com/place/163002/2c2fe06f-9c24-49c7-abde-ddaf8f23f7c4.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stratton [](https://expedia.ca/Stratton-Chalets.d163002-aaChalets.Travel-Guide-Accommodation) ![Drone view from above a West Dover Vermont neighborhood in winter](https://images.trvl-media.com/place/10459/36c3716b-92fb-40b7-8bcf-545492fddfe3.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### West Dover [](https://expedia.ca/West-Dover-Chalets.d10459-aaChalets.Travel-Guide-Accommodation) ![Autumn colors along Connecticut River, Brattleboro, Vermont](https://images.trvl-media.com/place/9636/028a402e-1933-4649-ba79-261aea048ad3.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Brattleboro [](https://expedia.ca/Brattleboro-Chalets.d9636-aaChalets.Travel-Guide-Accommodation) ![Wilmington which includes a city and autumn leaves](https://images.trvl-media.com/place/175314/9c0f0e5d-2a7c-4c89-8d88-0d1abb3d7c9a.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Wilmington [](https://expedia.ca/Wilmington-Chalets.d175314-aaChalets.Travel-Guide-Accommodation) ![White winter wonderland scenery in South Londonderry, Vermont with snow covered trees, bench, pond and blue cloudy sky in the background. Cold snowy day.](https://images.trvl-media.com/place/127228/def91bc0-833e-4f3b-aaad-ceb4dc0bf45d.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Londonderry [](https://expedia.ca/Londonderry-Chalets.d127228-aaChalets.Travel-Guide-Accommodation) ![HGY9XC View of the Ball Mountain Reservoir from the top of the Ball Mountain Dam on the West River in Jamaica Vermont USA](https://images.trvl-media.com/place/184052/aaff0c92-5112-4914-98bd-67915c0912e0.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Jamaica [](https://expedia.ca/Jamaica-Chalets.d184052-aaChalets.Travel-Guide-Accommodation) ## Our top choices for Windham County chalets ![Exterior](https://images.trvl-media.com/lodging/103000000/102410000/102409700/102409630/3e2c67da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/103000000/102410000/102409700/102409630/5aefc14a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102410000/102409700/102409630/0719e01a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/103000000/102410000/102409700/102409630/35cd5ba2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful- Ski/Golf home, Hot tub, mins to MTN [](https://www.expedia.ca/Wilmington-Hotels-Beautiful-SkiGolf-Home.h102409630.Hotel-Information) Wilmington 8.4/10 Very good (5 reviews) "we loved our stay there! having a home where you can cook, have everything you need to do so helps so much" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn F. [](https://www.expedia.ca/Wilmington-Hotels-Beautiful-SkiGolf-Home.h102409630.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122400000/122390200/122390180/f4c51bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/123000000/122400000/122390200/122390180/dba99d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/123000000/122400000/122390200/122390180/w1369h976x0y0-cea30437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122400000/122390200/122390180/c14ff50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont. [](https://www.expedia.ca/West-Townshend-Hotels-Cozy-3-Bedroom-2-Bathroom-Chalet-Centrally-Located-In-Southern-Vermont.h122390180.Hotel-Information) Windham 10/10 Exceptional (5 reviews) [](https://www.expedia.ca/West-Townshend-Hotels-Cozy-3-Bedroom-2-Bathroom-Chalet-Centrally-Located-In-Southern-Vermont.h122390180.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/125000000/124540000/124532800/124532764/6e00abd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124540000/124532800/124532764/78229567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124540000/124532800/124532764/731538ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124540000/124532800/124532764/19dc7b1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marvelous 3-bedroom chalet in charming Wilmington [](https://www.expedia.ca/Wilmington-Hotels-Marvelous-3-Bedroom-Chalet-In-Charming-Wilmington.h124532764.Hotel-Information) Wilmington 10/10 Exceptional (1 review) "The host, Jamie, was absolutely amazing! Very welcoming!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn L. [](https://www.expedia.ca/Wilmington-Hotels-Marvelous-3-Bedroom-Chalet-In-Charming-Wilmington.h124532764.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/42000000/41050000/41042300/41042264/712edc8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/42000000/41050000/41042300/41042264/111dcc27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41050000/41042300/41042264/a86561bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/42000000/41050000/41042300/41042264/96f4ef08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Chalet mins to Mt Snow - Clubhouse w/pool, mins to town for dining out. [](https://www.expedia.ca/Wilmington-Hotels-Vrbo-Property.h41042264.Hotel-Information) Wilmington 9.8/10 Exceptional (17 reviews) "Perfect for a family of four, close to Mt Snow" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elisabeth G. [](https://www.expedia.ca/Wilmington-Hotels-Vrbo-Property.h41042264.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/eda7773c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/909249f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/ec10883e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/e051b2f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly! [](https://www.expedia.ca/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information) Wardsboro 10/10 Exceptional (19 reviews) "We had an awesome time here. The property was well stocked with essentials, affordable us some opportunity to unwind, explore the creek, and hang out with the fire pit, board games, and the kids enjoyed the ridge racer arcade. Would absolutely come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph R. CA $246 CA $596 total includes taxes & fees Mar 10 - Mar 11 [](https://www.expedia.ca/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33560000/33556800/33556783/116b7c45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/34000000/33560000/33556800/33556783/3efb217a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33556800/33556783/ebfc5ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33560000/33556800/33556783/85477082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Bedroom Chalet, Charming, Quiet, River Front [](https://www.expedia.ca/Jamaica-Hotels-Two-Bedroom-Chalet.h33556783.Hotel-Information) Jamaica 9.4/10 Exceptional (77 reviews) "This place was just what we need to get away from big-city living for a week." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott P. [](https://www.expedia.ca/Jamaica-Hotels-Two-Bedroom-Chalet.h33556783.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/c71f56f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/7665cd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/26cdcbb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, Netflix, streaming services](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/341be75e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House [](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information) Dover 9.8/10 Exceptional (24 reviews) "Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SZU YIN C. CA $147 CA $598 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/5f637af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/38bc7f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/dcc44385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/4c3f61c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Charming Chalet with Hot Tub 1 Mile to Mt. Snow [](https://www.expedia.ca/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information) Dover 10/10 Exceptional (15 reviews) "This place was absolutely amazing! The pictures didn’t do this place justice. The ambience of the deck at night was magical. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaymari T. CA $613 CA $1,249 total includes taxes & fees Mar 11 - Mar 12 [](https://www.expedia.ca/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/93000000/92350000/92345400/92345304/9d6ca0e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/93000000/92350000/92345400/92345304/w750h498x0y2-45388ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92350000/92345400/92345304/09e6f36c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92350000/92345400/92345304/7469e1fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy ski chalet - w/ Assoc amenities. 10 mins from Mount Snow [](https://www.expedia.ca/Wilmington-Hotels-Cozy-Ski-Chalet-W-Assoc-Amenities-10-Mins-From-Mount-Snow.h92345304.Hotel-Information) Wilmington 10/10 Exceptional (14 reviews) "The house was kept in great condition and the owner Matt was fantastic with communicating through the Expedia app. Everything was exactly as he communicated and whenever I had questions, he replied very quickly, almost like it was a text message. The house had a working wood fireplace with plenty of wood, 3 bedrooms that could fit 4 in one room, 3 in one room, and 2 in another room. There plenty of towels and necesities needed for a large family or 2 families. The house was clean with large... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph [](https://www.expedia.ca/Wilmington-Hotels-Cozy-Ski-Chalet-W-Assoc-Amenities-10-Mins-From-Mount-Snow.h92345304.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90540000/90533700/90533684/d42651c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90540000/90533700/90533684/3dba94a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90540000/90533700/90533684/5333f9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90540000/90533700/90533684/b1e79af6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake [](https://www.expedia.ca/Wilmington-Hotels-HotTubGameRmTraeger-Smoker-15-Min-2-Mt-Snow.h90533684.Hotel-Information) Wilmington 10/10 Exceptional (7 reviews) "House was perfect for what we needed for our family road trip" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracy R. [](https://www.expedia.ca/Wilmington-Hotels-HotTubGameRmTraeger-Smoker-15-Min-2-Mt-Snow.h90533684.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/127000000/126130000/126120300/126120273/w1089h709x63y60-ef749c25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/127000000/126130000/126120300/126120273/w1079h591x63y65-bf61284b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/127000000/126130000/126120300/126120273/d9c8b023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, toilet paper](https://images.trvl-media.com/lodging/127000000/126130000/126120300/126120273/c7b96afd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy & Spacious Ski Condo 1 mile from Mount Snow VT [](https://www.expedia.ca/West-Dover-Hotels-Cozy-Spacious-Ski-Condo-1-Mile-From-Mount-Snow-VT.h126120273.Hotel-Information) Dover [](https://www.expedia.ca/West-Dover-Hotels-Cozy-Spacious-Ski-Condo-1-Mile-From-Mount-Snow-VT.h126120273.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123770000/123762300/123762202/c4de4794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123770000/123762300/123762202/d26e507b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/124000000/123770000/123762300/123762202/cd624751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/124000000/123770000/123762300/123762202/dbc322c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet With Mountain View Steps From Shuttle [](https://www.expedia.ca/West-Dover-Hotels-Chalet-With-Mountain-View-Steps-From-Shuttle.h123762202.Hotel-Information) Dover 10/10 Exceptional (1 review) "Clean, well maintained and a responsive host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim W. [](https://www.expedia.ca/West-Dover-Hotels-Chalet-With-Mountain-View-Steps-From-Shuttle.h123762202.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/6da0ce7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/526de6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/62ad9b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/d54b3197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton! [](https://www.expedia.ca/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information) Wardsboro 10/10 Exceptional (7 reviews) "Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen T. CA $307 CA $743 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99400000/99396000/99395981/4d9a520d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/100000000/99400000/99396000/99395981/01a6412f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99400000/99396000/99395981/3dfb42d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99400000/99396000/99395981/3b1344e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton Mountain Escape w Hot Tub|Deck|Projector [](https://www.expedia.ca/Jamaica-Hotels-Stratton-Mountain-Escape-W-Hot-TubDeckProjector.h99395981.Hotel-Information) East Jamaica 10/10 Exceptional (4 reviews) "Great place. Clean and well taken care of. No issues over 6 days!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin S. [](https://www.expedia.ca/Jamaica-Hotels-Stratton-Mountain-Escape-W-Hot-TubDeckProjector.h99395981.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/77000000/76840000/76836700/76836627/c6132a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76840000/76836700/76836627/0ffa2125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/77000000/76840000/76836700/76836627/69b04840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76840000/76836700/76836627/5dfa6dc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow [](https://www.expedia.ca/West-Dover-Hotels-Wine-Moose-Hot-Tub-Fireplace-Sauna-9min-To-Mt-Snow.h76836627.Hotel-Information) Dover 10/10 Exceptional (8 reviews) "We had a great time at the Wine Moose! The sauna kept us super warm in the super cold temps. Very very close to Mt. Snow and we also hit up Berkshire East and Magic an hour south and north respectively, easily. I'd recommend staying here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zach F. [](https://www.expedia.ca/West-Dover-Hotels-Wine-Moose-Hot-Tub-Fireplace-Sauna-9min-To-Mt-Snow.h76836627.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/89000000/88230000/88224200/88224197/c8de5919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88230000/88224200/88224197/d3ae127f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/89000000/88230000/88224200/88224197/67e9f747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88230000/88224200/88224197/7352323a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mount Snow Vermont - Ski - Snowboard - 6 miles [](https://www.expedia.ca/Wilmington-Hotels-Mt-Snow-Ski-Chalet.h88224197.Hotel-Information) Wilmington 10/10 Exceptional (23 reviews) "Easy accessible, great location , very clean and the hosts have everything to make you feel right at home , with this being said all this made for a very lovely stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce W. [](https://www.expedia.ca/Wilmington-Hotels-Mt-Snow-Ski-Chalet.h88224197.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78270000/78268700/78268642/89d5ef21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78270000/78268700/78268642/6de802ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78270000/78268700/78268642/b5de2673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78270000/78268700/78268642/882c31d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private 6 bedroom Chalet 5min to Mt Snow [](https://www.expedia.ca/West-Dover-Hotels-Private-6-Bedroom-Chalet-Less-Than-5min-To-Mt-Snow.h78268642.Hotel-Information) Dover 9.8/10 Exceptional (15 reviews) "Great stay and successful bachelor party, host was very accommodating with check-in & check-out timing. Several phenomenal golf courses within 10 minutes of the property, gorgeous views! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nick B. [](https://www.expedia.ca/West-Dover-Hotels-Private-6-Bedroom-Chalet-Less-Than-5min-To-Mt-Snow.h78268642.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78770000/78764500/78764436/366d52f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78770000/78764500/78764436/1c28e258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78770000/78764500/78764436/7228734e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78770000/78764500/78764436/d0ffa534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfy chalet near town, lake, skiing and hiking [](https://www.expedia.ca/Wilmington-Hotels-Comfy-Chalet-Near-Town.h78764436.Hotel-Information) Wilmington 10/10 Exceptional (14 reviews) "Nice property. Accurate listing. Clean and good communication. Had a great time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tom c. [](https://www.expedia.ca/Wilmington-Hotels-Comfy-Chalet-Near-Town.h78764436.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105430000/105423200/105423111/85ad6dd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/106000000/105430000/105423200/105423111/0b0f04c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/106000000/105430000/105423200/105423111/caf7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/106000000/105430000/105423200/105423111/w1268h844x1y4-e8ec2ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet at Mt Snow, ski-home, free shuttle [](https://www.expedia.ca/West-Dover-Hotels-Chalet-At-Mt-Snow.h105423111.Hotel-Information) Dover [](https://www.expedia.ca/West-Dover-Hotels-Chalet-At-Mt-Snow.h105423111.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32420000/32414600/32414574/d503be79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32420000/32414600/32414574/72ac6348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32420000/32414600/32414574/1c2e5510.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32420000/32414600/32414574/c593e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chimney Hill 15 mins to Mt Snow, Clubhouse w/indoor pool, VAST trail to house [](https://www.expedia.ca/Wilmington-Hotels-Chimney-Hill-House-7-Miles-To-Mount-Snow.h32414574.Hotel-Information) Wilmington 9.6/10 Exceptional (42 reviews) "Joe was nice and easy to talk to. Neighbors were all friendly and the pool area/clubhouse was nice, clean, and inviting. We enjoyed the duck pond for some small easy fishing. Friendly, cool town center about 14 minutes away. I think this place was perfect for the price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David Q. [](https://www.expedia.ca/Wilmington-Hotels-Chimney-Hill-House-7-Miles-To-Mount-Snow.h32414574.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=2026-03-16&endDate=2026-03-17®ionId=6057353&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_6057353) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VACATION_HOME) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CHALET) Condos [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CONDO) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APARTMENT) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VILLA) ![](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%2FWindham-County-Chalets.d6057353-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-County-Chalets.d6057353-aaChalets.Travel-Guide-Accommodation) ## Top Windham County Hotel Reviews ![Farm Road Estate](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/4a7d2d8e_y.jpg) ### Farm Road Estate 10/10 Excellent "Very clean room, all the necessary amenities in the room, comfortable bed, etc. Staff very friendly and helpful!" [](https://expedia.ca/West-Dover-Hotels-Farm-Road-Estate.h88730696.Hotel-Information) ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg) ### The Covered Bridge Inn 10/10 Excellent "My room was clean and spacious. Bed was very comfortable. Mini fridge and microwave a big plus! I normally stay at a different hotel when I come up to visit my family but I decided to try this hotel. I wasn't sure how it would be but I was pleasantly surprised! Clean, quiet and the gentleman who always seems to be at the front desk.. I'm sorry I can't remember his name is awesome! I was there for 3 weeks and I loved it! 10/10" [](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Hideaway Inn Mt. Snow](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b_y.jpg) ### Hideaway Inn Mt. Snow 10/10 Excellent "Very clean throughout. Great common areas with thoughtful amenities like games, chairs for eating takeout, and the best coffee/hot chocolate machine! " [](https://expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 10/10 Excellent "Good location for our needs and very comfortable" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Weekday Special ⛷️Stratton Slopeside Condo at The Landmark!🎿](https://images.trvl-media.com/lodging/120000000/119190000/119183500/119183470/88dcbf8d_y.jpg) ### Weekday Special ⛷️Stratton Slopeside Condo at The Landmark!🎿 10/10 Excellent "The place was beautiful and could not be in a better location! " [](https://expedia.ca/Stratton-Hotels-Stratton-Slopeside-Condo-At-The-Landmark-400-FEET-TO-LIFT.h119183470.Hotel-Information) ![Vikings Villages Resort](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 10/10 Excellent "Our stay exceeded expectations! Staff greeted us warmly & was helpful. As for our accommodations - immaculate, beautiful, and thoughtfully appointed. We even considered canceling our dinner reservations to stay in! This is the perfect place to get away from the noise and busyness of the world. I highly recommend and we will be back in the fall for hiking and unwinding. " [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Staff and clean room" [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Big Bears Lodge](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/5147c108_y.jpg) ### Big Bears Lodge 10/10 Excellent "Nice big rooms , very clean, good breakfast, outdoor hot tub, everything you need for a ski holiday stay " [](https://expedia.ca/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information) ![Kitzhof Inn](https://images.trvl-media.com/lodging/13000000/12030000/12026600/12026510/ffba9625_y.jpg) ### Kitzhof Inn 10/10 Excellent "We stayed there several times. The hospitality is fabulous. The breakfast every morning is delicious and plenty of food. Has plenty of room for their guests to hang out in the lodge with a fireplace and TV." [](https://expedia.ca/West-Dover-Hotels-Kitzhof-Inn.h12026510.Hotel-Information) ## Find out more about Windham County ## Windham County Chalets information | Number of reviews | 221 | | ----------------- | ---------- | | Accommodation | 71 Chalets | | Lowest Price | CA $598 | | Highest Price | CA $1,249 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Jamaica ](https://www.expedia.ca/3Star-Jamaica-Hotels.s30-0-d184052.Travel-Guide-Filter-Hotels) - [Hotels near Brattleboro Common ](https://www.expedia.ca/Brattleboro-Common-Hotels.0-l553248621561865132-0.Travel-Guide-Filter-Hotels) - [B&B in Brookline ](https://www.expedia.ca/Brookline-Bed-And-Breakfast.d3000459594-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Brookline ](https://www.expedia.ca/Brookline-Chalets.d3000459594-aaChalets.Travel-Guide-Accommodation) - [Hotels with a Pool in Brookline ](https://www.expedia.ca/Brookline-Hotels-Hotel-With-Pool.0-0-d3000459594-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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