Title: Top Chalets in Cheshire County in 2026 | Expedia.ca [Cheshire County Travel Guide](https://expedia.ca/Cheshire-County.dx553248635976430851)[Cheshire County Hotels](https://expedia.ca/Destinations-In-Cheshire-County.d553248635976430851.Hotel-Destinations)[Vacation Rentals in Cheshire County](https://expedia.ca/Destinations-In-Cheshire-County.d553248635976430851.Vacation-Rental-Destinations)[Cheshire County Car Rentals](https://expedia.ca/Destinations-In-Cheshire-County.d553248635976430851.Car-Rental-Destinations)[Cheshire County Vacations](https://expedia.ca/Cheshire-County.d553248635976430851.Destination-Travel-Guides) ![The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, New Hampshire, an unincorporated village of Winchester.](https://images.trvl-media.com/place/3000447144/529ffd18-db0c-4d9e-8844-fe610e44574f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Donny Campos ![](https://images.trvl-media.com/place/3000447144/529ffd18-db0c-4d9e-8844-fe610e44574f.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 [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&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 four months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&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) ## Top Cities in Cheshire County ![Keene showing a church or cathedral and a city](https://images.trvl-media.com/place/6057413/ea8c4de6-dd4d-46cd-95bb-3bd63ebc09ea.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Keene [](https://expedia.ca/Keene-Chalets.d6057413-aaChalets.Travel-Guide-Accommodation) ![New Hampshire rail trail through autumn maple trees](https://images.trvl-media.com/place/183580/a26a366f-1e86-4e1c-b71a-9545606e3c3e.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Rindge [](https://expedia.ca/Rindge-Chalets.d183580-aaChalets.Travel-Guide-Accommodation) ![#hiking.. i love hiking being out doors following a trail or just making my own fresh air and the out doors is amazing. i hike every chance i can close to home or travel to find new locations, I'm from akron Ohio but i love to travel this photo was from..one the best hikes i ever done ](https://images.trvl-media.com/place/183569/7e361115-2ee1-4e00-9d51-581c9007a526.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Jaffrey [](https://expedia.ca/Jaffrey-Chalets.d183569-aaChalets.Travel-Guide-Accommodation) ![Aerial winter view of Fitzwilliam, New Hampshire ](https://images.trvl-media.com/place/104340/6fa042d8-f5d2-4551-a4e1-8b2736cb31e3.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Fitzwilliam [](https://expedia.ca/Fitzwilliam-Chalets.d104340-aaChalets.Travel-Guide-Accommodation) ![Aerial view of West Swanzey New Hampshire in early fall ](https://images.trvl-media.com/place/6348108/1856e823-b9c5-4cc3-880a-1fd676222faf.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Swanzey [](https://expedia.ca/Swanzey-Chalets.d6348108-aaChalets.Travel-Guide-Accommodation) ![Walpole museum, New Hampshire](https://images.trvl-media.com/place/6123341/781d9745-7861-46d2-87d9-a4cf37f1812a.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Walpole [](https://expedia.ca/Walpole-Chalets.d6123341-aaChalets.Travel-Guide-Accommodation) ## Our top choices for Cheshire 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) ![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) ### 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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33580000/33575200/33575107/60edac18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33580000/33575200/33575107/16695989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33580000/33575200/33575107/e56ec866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/34000000/33580000/33575200/33575107/4cde1251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Lodging at Mount Snow with Hot Tub on Deck [](https://www.expedia.ca/Wilmington-Hotels-Beautiful-Lodging-At-Mount-Snow-With-Hot-Tub-On-Deck.h33575107.Hotel-Information) Wilmington 9.4/10 Exceptional (43 reviews) "My family and I loved our stay. This cabin had everything we needed and more. One thing we do wish we had was fans in the upstairs rooms, as we stayed in the summer time and it did get quite hot up there. The owners were very helpful, and amazing with communication. We would absolutely love to stay here again one day! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) lizzie m. [](https://www.expedia.ca/Wilmington-Hotels-Beautiful-Lodging-At-Mount-Snow-With-Hot-Tub-On-Deck.h33575107.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/3696f739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/d2180d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/0545aa58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/89cf30d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Adirondack Cabin with Sauna on Lake Monomonac [](https://www.expedia.ca/Rindge-Hotels-Beautiful-Adirondack-Cabin-With-Sauna-On-Lake-Monomonac.h106335693.Hotel-Information) Rindge 9.8/10 Exceptional (25 reviews) "This is a great property, and Jim is a wonderful host. He accommodated all our requests for sauna use and provided helpful tips about the area. We hope to return again one day!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leigh C. CA $336 CA $540 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Rindge-Hotels-Beautiful-Adirondack-Cabin-With-Sauna-On-Lake-Monomonac.h106335693.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78270000/78268700/78268642/b5de2673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78270000/78268700/78268642/07e377b4.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 (14 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) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/eda7773c.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) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/f7ab718d.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) ### 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 (16 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 $273 CA $632 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.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) ![Interior](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/2a2bd0e5.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) ![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 (11 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. [](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.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) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/26cdcbb4.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) ### 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 (22 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 $115 CA $560 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) ![Exterior](https://images.trvl-media.com/lodging/111000000/110630000/110628800/110628771/d5da5c9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110630000/110628800/110628771/00b34fef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110630000/110628800/110628771/eec2f586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/111000000/110630000/110628800/110628771/3e2b3e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Lux Cabin w/ Mtn Views | Fire Pit [](https://www.expedia.ca/Wardsboro-Hotels-Modern-Lux-Cabin-W-Mtn-Views-Fire-Pit.h110628771.Hotel-Information) Stratton 10/10 Exceptional (1 review) "Tommy was a fantastic host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelsey H. [](https://www.expedia.ca/Wardsboro-Hotels-Modern-Lux-Cabin-W-Mtn-Views-Fire-Pit.h110628771.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/46000000/45630000/45629700/45629607/a950fe0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/46000000/45630000/45629700/45629607/b0445178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/46000000/45630000/45629700/45629607/75b834db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/46000000/45630000/45629700/45629607/084907f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alpine Chalet with outdoor Jacuzzi 1 mile from ski lifts [](https://www.expedia.ca/West-Dover-Hotels-Alpine-Chalet-With-Outdoor-Jacuzzi-1-Mile-From-Ski-Lifts.h45629607.Hotel-Information) Dover 9.8/10 Exceptional (40 reviews) "House was clean and comfortable and would love to stay again next season! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven L. [](https://www.expedia.ca/West-Dover-Hotels-Alpine-Chalet-With-Outdoor-Jacuzzi-1-Mile-From-Ski-Lifts.h45629607.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) ![Interior](https://images.trvl-media.com/lodging/34000000/33560000/33556800/33556783/111d522a.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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33556800/33556783/ebfc5ba7.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 (76 reviews) "We knew the house was dated but a few things that should be improved. Was ok clean not real clean. Bathroom had wall to wall carpets and toilet and shower were not real clean. he bed in the Main bedroom bed looked beautiful, but it was way too soft. The other bedroom had two twin beds and not good for couples. Kitchen was dated. The highlights were the fireplace and the outdoor deck. the deck was amazing. we loved the fireplace." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) james p. [](https://www.expedia.ca/Jamaica-Hotels-Two-Bedroom-Chalet.h33556783.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236914/9fbe2d57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236914/263b6fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236914/fdd85e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236914/729be2f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vermont winter chalet near Mount Snow and Wilmington [](https://www.expedia.ca/West-Dover-Hotels-Post-And-Beam-Chalet-Close-To-Skiing.h74236914.Hotel-Information) West Dover 10/10 Exceptional (24 reviews) "Great place, close to everything, all amenities and most importantly great hosts!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael S. [](https://www.expedia.ca/West-Dover-Hotels-Post-And-Beam-Chalet-Close-To-Skiing.h74236914.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/112000000/111850000/111840800/111840737/f96da761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111850000/111840800/111840737/cb5c54cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111850000/111840800/111840737/ba4a4768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111850000/111840800/111840737/1ae2420c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom chalet next to skiing, hiking, boating and breweries [](https://www.expedia.ca/Bradford-Hotels-3-Bedroom-Chalet-Next-To-Skiing.h111840737.Hotel-Information) Bradford 10/10 Exceptional (10 reviews) "We had a very comfortable stay here. The house is clean with an extremely well- equipped kitchen, and plenty of space for a family. Hosts are easy to communicate with, and it was easy to relax & enjoy the lake!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brooke A. [](https://www.expedia.ca/Bradford-Hotels-3-Bedroom-Chalet-Next-To-Skiing.h111840737.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/a6a78255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/1ce3fb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/f2b8d538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/bcfc0861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet Mount Snow/Stratton Skiing/hiking [](https://www.expedia.ca/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information) East Dover 9.8/10 Exceptional (10 reviews) "Easy to find! Clean! Cozy!! Would definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy-michael G. CA $138 CA $572 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/fe04814b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/ef743cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/3a874a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/a1a0916f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly [](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information) West Dover 10/10 Exceptional (23 reviews) "Wonderful time..the home was very spacious and comfortable..great location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen P. CA $343 CA $971 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/cc65421b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/7d6bcc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/aaebfa4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/83acf129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private cabin: 7 mins to slopes, wood fireplace [](https://www.expedia.ca/West-Dover-Hotels-Private-Cabin-7-Mins-To-Slopes.h105982869.Hotel-Information) Dover 9.8/10 Exceptional (6 reviews) "We spent the week, excellent location and the home was exactly as described in listing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris R. CA $502 CA $1,115 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/West-Dover-Hotels-Private-Cabin-7-Mins-To-Slopes.h105982869.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/32000000/31380000/31373400/31373369/9b03f35d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/32000000/31380000/31373400/31373369/8b6f470e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31380000/31373400/31373369/051ddc1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31380000/31373400/31373369/b8469436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW. [](https://www.expedia.ca/West-Dover-Hotels-WE-ARE-BACK-COME-AND-ENJOY-YOUR-STAY-AT-OUR-TREE-HOUSE-LIKE.h31373369.Hotel-Information) West Dover 9.8/10 Exceptional (38 reviews) "Clean, spacious and perfect location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/West-Dover-Hotels-WE-ARE-BACK-COME-AND-ENJOY-YOUR-STAY-AT-OUR-TREE-HOUSE-LIKE.h31373369.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) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32420000/32414600/32414574/c593e5b8.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) ### 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 (41 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) ![Exterior](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1071x0y2-62744863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1070h1076x5y0-75daf8bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1076x0y4-eec2a42e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, foosball, books](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/84b8211e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub! [](https://www.expedia.ca/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.Hotel-Information) Dover 10/10 Exceptional (7 reviews) "We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris I. CA $345 CA $839 total includes taxes & fees Feb 24 - Feb 25 [](https://www.expedia.ca/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/394573d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/d3aa8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/6eef057c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/7eb92a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vikings Villages Resort - Double Bed Room [](https://www.expedia.ca/Brattleboro-Hotels-Vikings-Villages-Resort-Double-Bed-Room.h110890615.Hotel-Information) Guilford CA $239 CA $294 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Brattleboro-Hotels-Vikings-Villages-Resort-Double-Bed-Room.h110890615.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66890000/66885400/66885334/15cbdb6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/67000000/66890000/66885400/66885334/197850f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66885400/66885334/68939c1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66890000/66885400/66885334/98054c2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Listing! Golf/Ski home w/SteamRoom & Hot Tub [](https://www.expedia.ca/West-Dover-Hotels-New-Listing-GolfSki-Home-WSteamRoom-Hot-Tub.h66885334.Hotel-Information) Dover 9.8/10 Exceptional (8 reviews) "Beautiful house and property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arthur H. [](https://www.expedia.ca/West-Dover-Hotels-New-Listing-GolfSki-Home-WSteamRoom-Hot-Tub.h66885334.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=2026-02-18&endDate=2026-02-19®ionId=553248635976430851&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America®ionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America®ionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=APARTMENT) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America®ionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=APART_HOTEL) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America®ionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=COTTAGE) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America®ionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CABIN) Condos [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America®ionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America®ionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VILLA) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America®ionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CHALET) ![](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%2FCheshire-County-Chalets.d553248635976430851-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-County-Chalets.d553248635976430851-aaChalets.Travel-Guide-Accommodation) ## Top Cheshire County Hotel Reviews ![Newport Motel](https://images.trvl-media.com/lodging/24000000/23980000/23973200/23973185/aa0d3f32_y.jpg) ### Newport Motel 10/10 Excellent "Clean and felt new" [](https://expedia.ca/Newport-Hotels-Newport-Motel.h23973185.Hotel-Information) ![Hideaway Inn Mt.Sunapee](https://images.trvl-media.com/lodging/121000000/120350000/120341300/120341253/7f350a77_y.jpg) ### Hideaway Inn Mt.Sunapee 10/10 Excellent "Love the no contact, online check in/out. We got the room number and code texted to us, so we could go straight in. The room was spacious enough for our equipment (two snowboards + gear) and clean. The bed was comfortable. I also appreciated the little coffee bar set up in the common area. Plus the games room (though we didn't use it, it was nice to know it was there." [](https://expedia.ca/Newbury-Hotels-Hideaway-Inn-Mt-Snow.h120341253.Hotel-Information) ![Motel 6 Leominster, MA](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/fe9126d0_y.jpg) ### Motel 6 Leominster, MA 10/10 Excellent "Great 😊 " [](https://expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.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 "Friendly staff, clean rooms. " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 "Good" [](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Staff and room were great, even let me check in at 1:30am after getting stuck in the recent storm. The room was spotless and comfortable. " [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Great Wolf Lodge Boston / Fitchburg, MA](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/19aa1fc1_y.jpg) ### Great Wolf Lodge Boston / Fitchburg, MA 10/10 Excellent "Very good, we will return soon." [](https://expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "What's clean staff was friendly food was good bar was nice the buildings a little bit old " [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Valley Craft Ales](https://images.trvl-media.com/lodging/90000000/89220000/89214100/89214004/c9afe648_y.jpg) ### Valley Craft Ales 10/10 Excellent "Great spot" [](https://expedia.ca/Wilmington-Hotels-Valley-Craft-Ales.h89214004.Hotel-Information) ## Find out more about Cheshire County ## Cheshire County Chalets information | Number of reviews | 399 | | ----------------- | ---------- | | Accommodation | 79 Chalets | | Lowest Price | CA $294 | | Highest Price | CA $1,115 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - 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