Title: Cheshire County Vacation Home Rentals from CA $281: Search Top Private Vacation Homes for Rent | 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) ![Keene which includes street scenes and autumn leaves](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105278-Keene-And-Vicinity.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheshire County Vacation Rentals ## Compare and save ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Featured Vacation Homes in Cheshire County ![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/79a253e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/70342e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/d695e72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/01ff54d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely 2nd Floor Apartment Greenfield 10/10 Exceptional (37) "Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. " CA $162 CA $281 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33940000/33938600/33938577/184626f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33940000/33938600/33938577/6908c165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33940000/33938600/33938577/22a53237.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33940000/33938600/33938577/968e0566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow Wilmington 10/10 Exceptional (134) "This was our second time renting this property for a quick ski trip. The property is spacious, and well appointed. It really offers everything you need for a relaxing ski vacation. Love the game room and the space." [](https://www.expedia.ca/Wilmington-Hotels-Spacious-Three-Level-Home.h33938577.Hotel-Information) ![3 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71550000/71546900/71546851/5fc6b5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, table tennis, books](https://images.trvl-media.com/lodging/72000000/71550000/71546900/71546851/8f7be5d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/72000000/71550000/71546900/71546851/8c416ff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71550000/71546900/71546851/01bfc43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing Andover 9.0/10 Wonderful (27) "We were only 4 people, and it felt huge. The cabin is nice, but does show some aging here and there. Nothing that was an actual issue, though. The property with the pond, the fire pit area and the little playground is absolutely gorgeous, though. The cabin offers plenty of space with 4.5 separate sleeping areas (there is a large futon in the game room that could be used in an emergency, I guess). The livingroom/kitchen area is very spacious with great views. Will definitely consider this for... [](https://www.expedia.ca/Ludlow-Hotels-Secluded-Cabin-W-Private-Hot-Tub.h71546851.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33580000/33571200/33571119/3cc51106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33580000/33571200/33571119/d4ba0953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33580000/33571200/33571119/5ffc1e7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33580000/33571200/33571119/c3e86dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Beach And Mountain Lake Home Washington 9.6/10 Exceptional (123) "I loved the house with so many bits of history of times past. It was also nice that it had just about anything you could possibly need which makes packing less stressful. I would have loved to k ow more about the artwork that adorns the walls and yard. I felt very much at peace while there." [](https://www.expedia.ca/Washington-Hotels-Private-Beach-And-Mountain-Lake-Home.h33571119.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115610000/115608200/115608105/ac3f13b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games](https://images.trvl-media.com/lodging/116000000/115610000/115608200/115608105/94a3d43a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115610000/115608200/115608105/245c6b23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games](https://images.trvl-media.com/lodging/116000000/115610000/115608200/115608105/0d009088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful house w/ mountain views, fireplace, balcony, bbq, gameroom, w/d, a/c Dover 10/10 Exceptional (3) "Great family space. Comfortable furniture, well-stocked kitchen, close to restaurants. A/C units worked well." [](https://www.expedia.ca/West-Dover-Hotels-Beautiful-House-W-Mountain-Views.h115608105.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71940000/71933600/71933561/7fecb73f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71940000/71933600/71933561/4e1caa79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71940000/71933600/71933561/8aec4bee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/72000000/71940000/71933600/71933561/ce0724c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns Townshend 10/10 Exceptional (61) "We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything." [](https://www.expedia.ca/Townshend-Hotels-Modern-Private-Home-30-Acres-W-Pool.h71933561.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/102000000/101310000/101308900/101308872/6d1aaefe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/102000000/101310000/101308900/101308872/2bcb25bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101310000/101308900/101308872/38a37d4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101310000/101308900/101308872/241ee0c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 16 ppl 2 hot tubs, game room, fire pit Antrim 9.8/10 Exceptional (9) "Clean, lots of space, helpful host, hot tub was also nice" CA $502 CA $870 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Antrim-Hotels-12-Ppl-Two-Hot-Tubs.h101308872.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106036100/106036013/a02d1c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106040000/106036100/106036013/38cac6f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106040000/106036100/106036013/8e492ad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/107000000/106040000/106036100/106036013/e8e5f7bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Green Mountain Chapel // Old Church repositioned into 3 BR Londonderry 10/10 Exceptional (18) "This is a really beautiful place to stay. The kitchen has pretty much very your would need for a stay, and the host leaves little extras for you. Absolutely would stay here again." [](https://www.expedia.ca/South-Londonderry-Hotels-The-Green-Mountain-Chapel-Old-Church-Repositioned-Into-3-BR.h106036013.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33510000/33507400/33507349/c54ed9a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33507400/33507349/e947497e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games, books](https://images.trvl-media.com/lodging/34000000/33510000/33507400/33507349/35e623ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33507400/33507349/4aa483cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Happy Place On Lake Sunapee - 10 minutes from the ski resort Newbury 9.6/10 Exceptional (51) "We LOVED this place! The house was stocked with all of the essentials, including towels and linens. This made traveling there easier. The swimming area was great too!" [](https://www.expedia.ca/Newbury-Hotels-Happy-Place-On-Lake-Sunapee-10-Minutes-From-The-Ski-Resort.h33507349.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/w1114h746x0y9-9e33c846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/f164c130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/w1179h807x0y0-78265303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/4520780f_edited_2e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. Dover 10/10 Exceptional (7) "Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. " [](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Listing-True-Ski-In-Ski-Out-With-Private-Hot-Tub-Fire-Pit.h110896001.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70120000/70112300/70112206/342b2143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70120000/70112300/70112206/e0d7fc20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/71000000/70120000/70112300/70112206/74307286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70120000/70112300/70112206/f2baa7c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful, private log cabin with huge, relaxing screened porch Townshend 10/10 Exceptional (41) "The spot was amazing and everything was exactly what we wanted. " [](https://www.expedia.ca/Townshend-Hotels-The-Labrador-Lodge-Beautiful.h70112206.Hotel-Information) ![Smart TV, fireplace, DVD player, table tennis](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/429008d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/dc95f952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/2de9f2fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/de6e43f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Custom Built Timber Frame Home, Sleeps 11 Wilmington 10/10 Exceptional (106) "Home was big, clean, and close to mt snow. We had a great stay. Thanks!" [](https://www.expedia.ca/Wilmington-Hotels-Beautiful-Custom-Built-Timber-Frame-Home.h33709968.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90760000/90755100/90755067/eceee69f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90760000/90755100/90755067/05e0071a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90760000/90755100/90755067/b86afcb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90760000/90755100/90755067/52bad100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet private pond getaway New Ipswich 9.4/10 Exceptional (15) "We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!" [](https://www.expedia.ca/New-Ipswich-Hotels-Quiet-Private-Pond-Getaway.h90755067.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/115000000/114590000/114585300/114585236/6507d5eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/115000000/114590000/114585300/114585236/1c05b1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer](https://images.trvl-media.com/lodging/115000000/114590000/114585300/114585236/63288aa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/115000000/114590000/114585300/114585236/d621bd00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inviting Condo w Fire Place & Hot Tub Francestown 9.4/10 Exceptional (6) "We stayed for two nights and enjoyed our time here. We didn't get to use the hot tub, but we did use the fireplace. The condo was nice and cozy, and we would definitely stay here again." [](https://www.expedia.ca/Francestown-Hotels-Inviting-Condo-W-Fire-Place-Hot-Tub.h114585236.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/58000000/57130000/57120900/57120883/c7cf9ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57130000/57120900/57120883/9bdf7f9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57130000/57120900/57120883/00add351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57130000/57120900/57120883/9e1da9b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Modern A-Frame in Southern Vermont is The Place To BE! Whitingham 10/10 Exceptional (85) "A beautiful cabin in the woods. Very clean and a perfect stay." [](https://www.expedia.ca/Whitingham-Hotels-Beautiful-Modern-A-Frame-In-Southern-Vermont-Is-The-Place-To-BE.h57120883.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/a9ea01f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/8ebf8854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/b4c71f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/4e1069ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Hot Tub Escape Keene 9.6/10 Exceptional (20) "Nice house in a nice location. " CA $363 CA $601 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/f381a7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/1b9f75ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/057e890a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/a21405c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews Wilmington 10/10 Exceptional (225) "Great house, fantastically well equipped (kayaks, bikes etc). Excellent, very responsive host. View out over the lake is amazing. Really enjoyed our stay. " [](https://www.expedia.ca/Wilmington-Hotels-Amazing-Views.h31967482.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64420000/64410700/64410693/f8a8bfb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64420000/64410700/64410693/cba0a4d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/65000000/64420000/64410700/64410693/7f5d3456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/65000000/64420000/64410700/64410693/d0422b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Riverfront Home 7 Minutes to Stratton! Jamaica 10/10 Exceptional (33) "Perfect house for a few families to gather and have fun. " [](https://www.expedia.ca/Jamaica-Hotels-Spacious-Riverfront-Home-7-Minutes-To-Stratton.h64410693.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/27000000/26940000/26934100/26934055/8062756f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26940000/26934100/26934055/f7a468fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, Netflix, books, streaming services](https://images.trvl-media.com/lodging/27000000/26940000/26934100/26934055/8540014e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free internet, bed sheets](https://images.trvl-media.com/lodging/27000000/26940000/26934100/26934055/d36c75a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains West Wardsboro 9.0/10 Wonderful (68) "My husband and i enjoyed our stay. The cabin was very clean and comfortable. We would definitely rent it again." [](https://www.expedia.ca/West-Wardsboro-Hotels-Dog-Friendly-Cabin-In-The-Woods-With-Firepit-Ski-Golf-At-Nearby-Mountains.h26934055.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/70000000/69700000/69690100/69690074/e7479349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/70000000/69700000/69690100/69690074/6b7aafdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/70000000/69700000/69690100/69690074/18bccb0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69700000/69690100/69690074/53f2881b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes West Wardsboro 9.8/10 Exceptional (25) "Enjoyed our time together at this home and in this area of Vermont." [](https://www.expedia.ca/West-Wardsboro-Hotels-Family-Home-W-Great-Yard.h69690074.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20®ionId=553248635976430851&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-County-Private-Vacation-Homes.d553248635976430851-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-County-Private-Vacation-Homes.d553248635976430851-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Cheshire County Hotel Reviews ![Claremont Motor Lodge](//images.trvl-media.com/lodging/39000000/38320000/38317200/38317142/64648cb7_y.jpg) ### Claremont Motor Lodge 10/10 Excellent "Room was clean and comfortable " [](https://expedia.ca/Mount-Sunapee-Hotels-Claremont-Motor-Lodge.h38317142.Hotel-Information) ![Pointe at Castle Hill Resort](//images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Well appointed room." [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![The Colonial Hotel](//images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "Huge place. Great restaurant and quiet area" [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Doubletree by Hilton Hotel Leominster](//images.trvl-media.com/lodging/1000000/20000/16700/16645/7570cba8_y.jpg) ### Doubletree by Hilton Hotel Leominster 10/10 Excellent "Room was very clean customer service was amazing we love staying here and will everytime we go to see our granddaughter." [](https://expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information) ![Great Wolf Lodge Boston / Fitchburg, MA](//images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/19aa1fc1_y.jpg) ### Great Wolf Lodge Boston / Fitchburg, MA 10/10 Excellent "Everything about this place was incredible " [](https://expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) ![Mountaineer Inn](//images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/7d61f01d_y.jpg) ### Mountaineer Inn 10/10 Excellent "The property was well kept and was close to different trails and beautiful views. We felt safe and comfortable. We want to come back in the winter to stay again! " [](https://expedia.ca/West-Dover-Hotels-Mountaineer-Inn.h82906124.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "Very clean, up to date, affordable" [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Riverside Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg) ### Riverside Hotel, an Ascend Collection Hotel 10/10 Excellent "What a lovely delight near the New Hampshire/Vermont border! The staff is very welcoming, the room is beautiful and clean, and the sunrise/sunset on the river are remarkable! When I accidently left behind something precious, they were quick to send it to me. This is an overall gem of a hotel. " [](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Nice big room for the money " [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ## Find out more about Cheshire County ## Cheshire County Vacation Homes information | Number of reviews | 1,005 | | --- | --- | | Accommodation | 685 Vacation Homes | | Lowest Price | CA $281 | | Highest Price | CA $870 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Monadnock Region](https://www.expedia.ca/3Star-Monadnock-Region-Hotels.s30-0-d553248635975749761.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Keene](https://www.expedia.ca/4Star-Keene-Hotels.s40-0-d6057413.Travel-Guide-Filter-Hotels) - [Hotels near Asbury United Methodist Church](https://www.expedia.ca/Asbury-United-Methodist-Church-Hotels.0-l6265749-0.Travel-Guide-Filter-Hotels) - 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