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 In two weeks [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 [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-04-10&endDate=2026-04-12&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) ## Our top choices for Cheshire County villas ![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/ea2acf6a.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/a011cb3b.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/e5516f66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Keene [](https://www.expedia.ca/Keene-Hotels-Keene-Villa-Near-Golf-Course-Swimming-Holes.h94952707.Hotel-Information) [](https://www.expedia.ca/Keene-Hotels-Keene-Villa-Near-Golf-Course-Swimming-Holes.h94952707.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=2026-01-02&endDate=2026-01-03®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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=VACATION_HOME) 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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=APART_HOTEL) 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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=APARTMENT) 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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=VILLA) 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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=COTTAGE) 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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&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 ![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 "I arrived far before published check-in time and only had to wait a reasonable amount of time to get into my room. Desk clerks were efficient and friendly. Clean, comfortable room. " [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.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 "Overall excellent " [](https://expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.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 "Good breakfast buffet" [](https://expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "Easy checkin, pleasant staff and clean room. " [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.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 "The people who work there are great! Very attentive. The location is very accessible and a rocks throw from the entrance to MT Sunapee Ski Area." [](https://expedia.ca/Newbury-Hotels-Hideaway-Inn-Mt-Snow.h120341253.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 "Yea" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![The White House Inn](https://images.trvl-media.com/lodging/3000000/2940000/2937400/2937372/fe9c2db1_y.jpg) ### The White House Inn 10/10 Excellent "There was no hot water the first night.. I let the staff know the next day .. the young man immediately checked room availability and offered 3 options.. he also asked if he could help move us The room was clean. The fireplace was wonderful staff was friendly and accommodating " [](https://expedia.ca/Wilmington-Hotels-White-House-Inn.h2937372.Hotel-Information) ![Valley Craft Ales](https://images.trvl-media.com/lodging/90000000/89220000/89214100/89214004/c9afe648_y.jpg) ### Valley Craft Ales 10/10 Excellent "Very easy check in process. They let us know due to it being a pub, it would be loud, but it was very quiet and easy to sleep! The pub area was lovely and had a huge chimney fire for everyone to enjoy and keep warm. The room was clean and well kept! Great experience! " [](https://expedia.ca/Wilmington-Hotels-Valley-Craft-Ales.h89214004.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 "It was very enjoyable, and so much to do. Great for the whole family " [](https://expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) ## Find out more about Cheshire County ## Cheshire County Villas information | Number of reviews | | | ----------------- | -------- | | 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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