Title: Top Chalets in Windham County from $421 - Expedia.com [Windham County Travel Guide](https://expedia.com/Windham-County.dx6057353)[Windham County Hotels](https://expedia.com/Destinations-In-Windham-County.d6057353.Hotel-Destinations)[Vacation Rentals in Windham County](https://expedia.com/Destinations-In-Windham-County.d6057353.Vacation-Rental-Destinations)[Windham County Flights](https://expedia.com/Destinations-In-Windham-County.d6057353.Flight-Destinations)[Things to do in Windham County](https://expedia.com/Things-To-Do-In-Windham-County.d6057353.Travel-Guide-Activities)[Car Rentals in Windham County](https://expedia.com/Destinations-In-Windham-County.d6057353.Car-Rental-Destinations)[Windham County Vacations](https://expedia.com/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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 20 - Mar 22](https://www.expedia.com/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.com/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.com/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.com/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.com/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.com/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.com/Brattleboro-Chalets.d9636-aaChalets.Travel-Guide-Accommodation) ![Wilmington featuring 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.com/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.com/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.com/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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102410000/102409700/102409630/b0ed4bb8.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) ### Chalet in Wilmington [](https://www.expedia.com/Wilmington-Hotels-Beautiful-SkiGolf-Home.h102409630.Hotel-Information) 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.com/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) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122400000/122390200/122390180/c14ff50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122400000/122390200/122390180/55e0bfc9.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) ### Chalet in Windham [](https://www.expedia.com/West-Townshend-Hotels-Cozy-3-Bedroom-2-Bathroom-Chalet-Centrally-Located-In-Southern-Vermont.h122390180.Hotel-Information) 10/10 Exceptional (5 reviews) [](https://www.expedia.com/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/c9ec97e8.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) ![Interior](https://images.trvl-media.com/lodging/125000000/124540000/124532800/124532764/78229567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Wilmington [](https://www.expedia.com/Wilmington-Hotels-Marvelous-3-Bedroom-Chalet-In-Charming-Wilmington.h124532764.Hotel-Information) 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.com/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) ![Property grounds](https://images.trvl-media.com/lodging/42000000/41050000/41042300/41042264/7fffe21d.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) ![Outdoor dining](https://images.trvl-media.com/lodging/42000000/41050000/41042300/41042264/111dcc27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Wilmington [](https://www.expedia.com/Wilmington-Hotels-Chimney-Hill-House-Mount-Snow-Area-Clubhouse-Windoor-Pool-2324-Ski-Season.h41042264.Hotel-Information) 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.com/Wilmington-Hotels-Chimney-Hill-House-Mount-Snow-Area-Clubhouse-Windoor-Pool-2324-Ski-Season.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) ![Interior](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/e051b2f3.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) ### Chalet in Wardsboro [](https://www.expedia.com/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information) 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. $373 nightly $421 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/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) ### Chalet in Jamaica [](https://www.expedia.com/Jamaica-Hotels-Two-Bedroom-Chalet.h33556783.Hotel-Information) 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.com/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) ![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) ![Interior](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/e73412a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Dover [](https://www.expedia.com/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information) 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. $390 nightly $441 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/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) ![Interior](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/6b8b3cc5.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) ![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) ### Chalet in Dover [](https://www.expedia.com/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information) 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. $743 nightly $840 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/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) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92350000/92345400/92345304/09e6f36c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/93000000/92350000/92345400/92345304/bc75c656.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) ### Chalet in Wilmington [](https://www.expedia.com/Wilmington-Hotels-Cozy-Ski-Chalet-W-Assoc-Amenities-10-Mins-From-Mount-Snow.h92345304.Hotel-Information) 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.com/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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90540000/90533700/90533684/12ef1930.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) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90540000/90533700/90533684/3dba94a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Wilmington [](https://www.expedia.com/Wilmington-Hotels-HotTubGameRmTraeger-Smoker-15-Min-2-Mt-Snow.h90533684.Hotel-Information) 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.com/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) ![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) ![Exterior](https://images.trvl-media.com/lodging/127000000/126130000/126120300/126120273/w1079h591x63y65-bf61284b.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) ### Chalet in Dover [](https://www.expedia.com/West-Dover-Hotels-Cozy-Spacious-Ski-Condo-1-Mile-From-Mount-Snow-VT.h126120273.Hotel-Information) [](https://www.expedia.com/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) ![TV, fireplace](https://images.trvl-media.com/lodging/124000000/123770000/123762300/123762202/dbc322c7.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) ![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) ### Chalet in Dover [](https://www.expedia.com/West-Dover-Hotels-Chalet-With-Mountain-View-Steps-From-Shuttle.h123762202.Hotel-Information) 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.com/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) ![Interior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/3bd9f0bc.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) ### Chalet in Wardsboro [](https://www.expedia.com/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information) 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. $475 nightly $537 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/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) ![Outdoor spa tub](https://images.trvl-media.com/lodging/100000000/99400000/99396000/99395981/e7bf162c.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) ![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) ### Chalet in East Jamaica [](https://www.expedia.com/Jamaica-Hotels-Stratton-Mountain-Escape-W-Hot-TubDeckProjector.h99395981.Hotel-Information) 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.com/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) ![Dining](https://images.trvl-media.com/lodging/77000000/76840000/76836700/76836627/5dfa6dc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76840000/76836700/76836627/21ef6a78.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) ### Chalet in Dover [](https://www.expedia.com/West-Dover-Hotels-Wine-Moose-Hot-Tub-Fireplace-Sauna-9min-To-Mt-Snow.h76836627.Hotel-Information) 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.com/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) ![Interior](https://images.trvl-media.com/lodging/89000000/88230000/88224200/88224197/7352323a.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/d2abf5eb.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) ### Chalet in Wilmington [](https://www.expedia.com/Wilmington-Hotels-Mt-Snow-Ski-Chalet.h88224197.Hotel-Information) 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.com/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) ![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) ![Interior](https://images.trvl-media.com/lodging/79000000/78270000/78268700/78268642/6de802ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Dover [](https://www.expedia.com/West-Dover-Hotels-Private-6-Bedroom-Chalet-Less-Than-5min-To-Mt-Snow.h78268642.Hotel-Information) 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.com/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) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78770000/78764500/78764436/7228734e.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) ![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) ### Chalet in Wilmington [](https://www.expedia.com/Wilmington-Hotels-Comfy-Chalet-Near-Town.h78764436.Hotel-Information) 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.com/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/a168fe4a.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 in Dover [](https://www.expedia.com/West-Dover-Hotels-Chalet-At-Mt-Snow.h105423111.Hotel-Information) [](https://www.expedia.com/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) ![Dining](https://images.trvl-media.com/lodging/33000000/32420000/32414600/32414574/804aa01f.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) ### Chalet in Wilmington [](https://www.expedia.com/Wilmington-Hotels-Chimney-Hill-House-7-Miles-To-Mount-Snow.h32414574.Hotel-Information) 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.com/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.com/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.com/deals?rfrr=AA_SPRING_PROMO_6057353) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/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.com/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.com/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.com/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.com/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) Cottages [](https://www.expedia.com/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) Apartments [](https://www.expedia.com/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) Villas [](https://www.expedia.com/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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindham-County-Chalets.d6057353-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-County-Chalets.d6057353-aaChalets.Travel-Guide-Accommodation) ## Top Windham County Hotel Reviews ![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.com/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "We loved our stay at the Black Bear! The check-in went smoothly with desk staff, Noah. She was very helpful and went over everything about our stay. The room was very clean. The hot tub was very nice and clean and a welcome after a day on the slopes. The shuttle to the mountain was great and ran frequently. The breakfast was always hot and had many options. We would definitely stay there again!" [](https://expedia.com/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.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 "The community spaces really stood out and we spent a lot of time enjoying those. " [](https://expedia.com/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) ![Farm Road Estate](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/4a7d2d8e_y.jpg) ### Farm Road Estate 10/10 Excellent "Room was spotless, very beautiful. Staff was attentive. Great restaurants on site. Very close to the mountain. We loved our short stay at Farm Road Estate! " [](https://expedia.com/West-Dover-Hotels-Farm-Road-Estate.h88730696.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.com/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.com/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.com/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.com/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.com/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information) ## Find out more about Windham County ## Windham County Chalets information | Number of reviews | 221 | | ----------------- | ---------- | | Accommodation | 71 Chalets | | Lowest Price | $421 | | Highest Price | $840 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - 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