Title: Cheshire County Villas | 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 # Search Cheshire County Villa Rentals ## Compare and save - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Cheshire County ![Keene showing a church or cathedral and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105281-Keene-And-Vicinity.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Keene [](https://expedia.ca/Keene-Villas.d6057413-aaVillas.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/72de8a56710436641f0aeeaf3b0e190c.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Rindge [](https://expedia.ca/Rindge-Villas.d183580-aaVillas.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/9b320961fd585a1c4407ed1c1d8d7b7c.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Jaffrey [](https://expedia.ca/Jaffrey-Villas.d183569-aaVillas.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/5e2a1004c09afc894c2b79e348e0430b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Walpole [](https://expedia.ca/Walpole-Villas.d6123341-aaVillas.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/23b4161961eb757bd6886ce6ea416c5e.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### West Chesterfield [](https://expedia.ca/West-Chesterfield-Villas.d183592-aaVillas.Travel-Guide-Accommodation) ## Featured Villas in Cheshire County ![Exterior](https://images.trvl-media.com/lodging/103000000/102120000/102116300/102116254/fa95b79a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102120000/102116300/102116254/95faaff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102120000/102116300/102116254/cde0156e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/103000000/102120000/102116300/102116254/a9e90f8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Birch. A Spacious Mansion 2 min from Mt. Snow! Dover 6.0/10 (1) "Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison S. [](https://www.expedia.ca/West-Dover-Hotels-The-Birch-House-Heated-Pool.h102116254.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115510000/115500600/115500556/aac35b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115510000/115500600/115500556/e3dc0cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115510000/115500600/115500556/2648c880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115510000/115500600/115500556/w2048h1364x0y0-356ad040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Myrtle. Outdoor hot tub H Pool-Tennis & More Dover [](https://www.expedia.ca/West-Dover-Hotels-The-Myrtle-House-Heated-Pool-Hot-Tub-Tennis-More.h115500556.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/122000000/121120000/121114200/121114136/42fda579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121120000/121114200/121114136/87712171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121120000/121114200/121114136/72c4952f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121120000/121114200/121114136/cb9096b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Rosewood. Outdoor Hot tub. Indoor H pool& more West Dover 9.0/10 Wonderful (46) "Excellent house for a multi family trip to vermont. Well maintained, with a very nice indoor pool, spa, etc which kids really loved." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dheeraj P. [](https://www.expedia.ca/West-Dover-Hotels-The-Rosewood-House-Indoor-Pool-Spa-Sauna-More.h121114136.Hotel-Information) ![Villa (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94952800/94952707/b880a755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94952800/94952707/4ddb7537.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94952800/94952707/ae8d7d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94952800/94952707/3e31d948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keene Villa Near Skiing, Swimming & Hiking! Keene [](https://www.expedia.ca/Keene-Hotels-Keene-Villa-Near-Golf-Course-Swimming-Holes.h94952707.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122210000/122208100/122208087/7c0eea60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122210000/122208100/122208087/555adf5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122210000/122208100/122208087/0a7b3391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/123000000/122210000/122208100/122208087/8b826b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Construction- min from Mt, Hot tub, Shuttle Dover [](https://www.expedia.ca/West-Dover-Hotels-New-Construction-Min-From-Mt.h122208087.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522985/1d986bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522985/487432a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522985/ba8ca65b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522985/3019c4e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Artist's Own Luxury Residence Newfane Vermont - Stunning Views 25 Acres Newfane 10/10 Exceptional (13) "The house is beautiful and Nancy is a great host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ronald B. [](https://www.expedia.ca/Newfane-Hotels-Artists-Own-Luxury-Residence-Newfane-Vermont-Stunning-Views-25-Acres.h32522985.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/107000000/106410000/106404800/106404757/w904h683x60y0-a63bd6e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106410000/106404800/106404757/w908h683x58y0-788fd869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/107000000/106410000/106404800/106404757/w905h683x60y0-d161f7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106410000/106404800/106404757/eced85dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa privacy, luxury & relaxation inside or out. Exceptional conveniences Lyndeborough [](https://www.expedia.ca/Lyndeborough-Hotels-Villa-Privacy.h106404757.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121120000/121114200/121114131/29ed7341.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121120000/121114200/121114131/577a8ea2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121120000/121114200/121114131/896e36b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121120000/121114200/121114131/21c28136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mahogany. Outside hot tub, Indoor pool,&Game R Dover 8.0/10 Very good (25) "We held a family reunion at the Brown House. It was an absolutely amazing week. The house has so much to offer, the indoor pool and hot tub were a gathering spot for the kids. With each bedroom having its own private bathroom, it was like each family had their own private hotel room. The kitchen was big and well stocked with all the cooking gear you would ever need. The property manager, Tony was so responsive and friendly for any question or need he was always right there. The location is... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul P. [](https://www.expedia.ca/West-Dover-Hotels-The-Mahogany-House-Indoor-Pool-Spa-SaunaGameroom.h121114131.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/121000000/120260000/120251900/120251894/30a32984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120260000/120251900/120251894/3bd33b3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120260000/120251900/120251894/6b172080.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/121000000/120260000/120251900/120251894/6b690229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kingswood-20B-Townhome- Hot tub, Shuttle, Clubhouse Dover [](https://www.expedia.ca/West-Dover-Hotels-Kingswood-20B-Towhome-Hot-Tub.h120251894.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=2025-12-20&endDate=2025-12-21®ionId=553248635976430851&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style 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=2026-03-06&d1=2026-03-06&endDate=2026-03-09&d2=2026-03-09&lodging=CABIN) 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=2026-03-06&d1=2026-03-06&endDate=2026-03-09&d2=2026-03-09&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=2026-03-06&d1=2026-03-06&endDate=2026-03-09&d2=2026-03-09&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=2026-03-06&d1=2026-03-06&endDate=2026-03-09&d2=2026-03-09&lodging=APART_HOTEL) 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=2026-03-06&d1=2026-03-06&endDate=2026-03-09&d2=2026-03-09&lodging=CONDO) 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=2026-03-06&d1=2026-03-06&endDate=2026-03-09&d2=2026-03-09&lodging=COTTAGE) 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=2026-03-06&d1=2026-03-06&endDate=2026-03-09&d2=2026-03-09&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=2026-03-06&d1=2026-03-06&endDate=2026-03-09&d2=2026-03-09&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-Villas.d553248635976430851-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-County-Villas.d553248635976430851-aaVillas.Travel-Guide-Accommodation) ## Top Cheshire County Hotel Reviews ![Hideaway Inn Mt.Sunapee](https://images.trvl-media.com/lodging/121000000/120350000/120341300/120341253/7f350a77_y.jpg) ### Hideaway Inn Mt.Sunapee 10/10 Excellent "Nice" [](https://expedia.ca/Newbury-Hotels-Hideaway-Inn-Mt-Snow.h120341253.Hotel-Information) ![Doubletree by Hilton Hotel Leominster](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/7570cba8_y.jpg) ### Doubletree by Hilton Hotel Leominster 10/10 Excellent "Very clean. Staff was friendly. " [](https://expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information) ![Valley Craft Ales](https://images.trvl-media.com/lodging/90000000/89220000/89214100/89214004/c9afe648_y.jpg) ### Valley Craft Ales 10/10 Excellent "The room was very clean and warm. Perfect for a weekend ski trip. Self check in and out. The walls are thin but everyone was quiet by 10\. The food at the restaurant was delicious. " [](https://expedia.ca/Wilmington-Hotels-Valley-Craft-Ales.h89214004.Hotel-Information) ![Mountaineer Inn](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/7d61f01d_y.jpg) ### Mountaineer Inn 10/10 Excellent "The room was very clean and the beds were comfortable. The location, at the base of Mt. Snow is great. The hotel had nice decor and a free coffee bar. No breakfast, but that was ok. We never saw anyone that worked there, but that was ok too as we were sent our room # and code on the day of check-in and never had any issues." [](https://expedia.ca/West-Dover-Hotels-Mountaineer-Inn.h82906124.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "The customer service at this hotel is consistently exceptional. Every staff member is friendly, professional, and welcoming, creating an atmosphere that feels truly comfortable. The property is impeccably clean, and the breakfast offerings are always enjoyable. I have had an excellent experience during each of my visits, and I highly recommend this hotel to others" [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.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 "We had a great time.. lots to do." [](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 "Have stayed here over past years. Always good stay." [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Riverside Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg) ### Riverside Hotel, an Ascend Collection Hotel 10/10 Excellent "All good" [](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![Hampton Inn & Suites Greenfield](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg) ### Hampton Inn & Suites Greenfield 10/10 Excellent "Staff was friendly, room was very nice and really appreciate the breakfast." [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ## Find out more about Cheshire County ## Cheshire County Villas information | Number of reviews | 72 | | ----------------- | -------- | | Accommodation | 7 Villas | | Lowest Price | | | Highest Price | | ## 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) - [Chesterfield Hotels ](https://www.expedia.ca/Chesterfield-Hotels.d6052872.Travel-Guide-Hotels) - [Hotels near Colonial Theatre ](https://www.expedia.ca/Colonial-Theatre-Hotels.0-l553248621532666941-0.Travel-Guide-Filter-Hotels) - 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