Title: Cheshire County Vacation Home Rentals from CA $280: 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)

![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)

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## Check prices for these dates

In two weeks

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976430851&startDate=2026-05-15&endDate=2026-05-17&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-Private-Vacation-Homes.d6057413-aaPrivateVacationHomes.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-Private-Vacation-Homes.d183569-aaPrivateVacationHomes.Travel-Guide-Accommodation)

![Stunning ](https://images.trvl-media.com/place/183580/5db4cf02-8733-4624-b79e-00274997b61d.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Rindge

[](https://expedia.ca/Rindge-Private-Vacation-Homes.d183580-aaPrivateVacationHomes.Travel-Guide-Accommodation)

![Petroglyphs carved into the rocks along the connecticut river in vt.](https://images.trvl-media.com/place/6123341/a0d75d64-c95b-4611-b551-1f08145f2c0c.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Walpole

[](https://expedia.ca/Walpole-Private-Vacation-Homes.d6123341-aaPrivateVacationHomes.Travel-Guide-Accommodation)

![Beautiful spot during fall. A gurgling stream besides it has multiple photo opps for long exposure ](https://images.trvl-media.com/place/6348108/8241d456-e5b4-45a9-a81f-c1955c09b4b0.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Swanzey

[](https://expedia.ca/Swanzey-Private-Vacation-Homes.d6348108-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Our top choices for Cheshire County vacation homes

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/c077bee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/b4b598c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/eb8c4f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/212e023d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Colrain Winter Adventure- Hot Tub, Air Hockey, Fire Pit

[](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information)

Colrain

9.8/10

Exceptional

(40 reviews)

"Great house for family gatherings "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

John Paul B.

CA $606

CA $1,152 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/d47a45c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/f381a7e2.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)

![Interior](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/fb67a6db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

[](https://www.expedia.ca/Wilmington-Hotels-Amazing-Views.h31967482.Hotel-Information)

Wilmington

10/10

Exceptional

(229 reviews)

"Spectacular view and very peaceful."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Beth B.

[](https://www.expedia.ca/Wilmington-Hotels-Amazing-Views.h31967482.Hotel-Information)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/72000000/71130000/71123500/71123428/c18d0f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71130000/71123500/71123428/4492adea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71130000/71123500/71123428/f467af90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71130000/71123500/71123428/d961b9fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

[](https://www.expedia.ca/West-Dover-Hotels-500ft-Across-The-Street-To-Carnitha-Gromet-To-Main-Lift-Or-Take-Moover-To-Base.h71123428.Hotel-Information)

Dover

10/10

Exceptional

(52 reviews)

"Overall a nice stay, thanks Jen!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

[](https://www.expedia.ca/West-Dover-Hotels-500ft-Across-The-Street-To-Carnitha-Gromet-To-Main-Lift-Or-Take-Moover-To-Base.h71123428.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)

![Interior](https://images.trvl-media.com/lodging/34000000/33580000/33571200/33571119/w400h298x0y2-5e5259d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33580000/33571200/33571119/c418832c.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

[](https://www.expedia.ca/Washington-Hotels-Private-Beach-And-Mountain-Lake-Home.h33571119.Hotel-Information)

Washington

9.6/10

Exceptional

(125 reviews)

"This home has absolutely everything you need. The private beach is accessed through a short pleasant walk through the woods and it’s beautiful. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrea M.

[](https://www.expedia.ca/Washington-Hotels-Private-Beach-And-Mountain-Lake-Home.h33571119.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/dc95f952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/w800h599x0y1-e8a3be7f.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/b96118f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### Beautiful Custom Built Timber Frame Home, Sleeps 11

[](https://www.expedia.ca/Wilmington-Hotels-Beautiful-Custom-Built-Timber-Frame-Home.h33709968.Hotel-Information)

Wilmington

10/10

Exceptional

(109 reviews)

"We had an excellent stay. Clean rooms. Well stocked with all everything you need. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Thomas K.

[](https://www.expedia.ca/Wilmington-Hotels-Beautiful-Custom-Built-Timber-Frame-Home.h33709968.Hotel-Information)

![Spa](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/6aa98084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/f08a0feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/47ed0857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/1c538637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

[](https://www.expedia.ca/West-Dover-Hotels-Beautifully-Renovated-Mount-Snow-Luxury-Chalet-Sleeps-12.h18956475.Hotel-Information)

West Dover Vermont

9.6/10

Exceptional

(28 reviews)

"Perfect location to walk to slopes. The host was phenomenal! Very responsive and helpful. Can’t wait to stay again soon!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

R B.

[](https://www.expedia.ca/West-Dover-Hotels-Beautifully-Renovated-Mount-Snow-Luxury-Chalet-Sleeps-12.h18956475.Hotel-Information)

![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)

![Dining](https://images.trvl-media.com/lodging/65000000/64420000/64410700/64410693/c1345386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/65000000/64420000/64410700/64410693/27fe11ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious Riverfront Home 7 Minutes to Stratton!

[](https://www.expedia.ca/Jamaica-Hotels-Spacious-Riverfront-Home-7-Minutes-To-Stratton.h64410693.Hotel-Information)

Jamaica

10/10

Exceptional

(37 reviews)

"Had a great time in VT, a perfect place to relax and enjoy time with family."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sue T.

[](https://www.expedia.ca/Jamaica-Hotels-Spacious-Riverfront-Home-7-Minutes-To-Stratton.h64410693.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101310000/101308900/101308872/1c5c7e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101310000/101308900/101308872/a4d1f01b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/102000000/101310000/101308900/101308872/f72e091b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101310000/101308900/101308872/d53a4174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 16 ppl 2 hot tubs, game room, fire pit

[](https://www.expedia.ca/Antrim-Hotels-12-Ppl-Two-Hot-Tubs.h101308872.Hotel-Information)

Antrim

9.8/10

Exceptional

(9 reviews)

"This was a great property. We had a wonderful stay here for a large group. Rebecca is a great host- so responsive and helpful before and during our stay. Highly recommend! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kyra D.

CA $248

CA $562 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Antrim-Hotels-12-Ppl-Two-Hot-Tubs.h101308872.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107610000/107605300/107605272/1f5594bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107610000/107605300/107605272/7474f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107610000/107605300/107605272/w3716h2086x0y6-8bc9f5f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107610000/107605300/107605272/6d7743ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Stylish-New-2-Bedroom-Property-In-Enchanting-Shelburne-Falls-Village.h107605272.Hotel-Information)

Shelburne Falls

10/10

Exceptional

(20 reviews)

"Kevin's place is fantastic — clean, spacious, bright, and is in a great location, just a short walk from town. I would absolutely recommend this VRBO rental!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Allison E.

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Stylish-New-2-Bedroom-Property-In-Enchanting-Shelburne-Falls-Village.h107605272.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/5908be8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/1ac33e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/af7444a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/2b07dc5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury prop, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV

[](https://www.expedia.ca/Townshend-Hotels-Luxurious.h119523119.Hotel-Information)

Townshend

10/10

Exceptional

(9 reviews)

"Had a great time . Excellent communication Very clean .Would definitely stay there again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris R.

[](https://www.expedia.ca/Townshend-Hotels-Luxurious.h119523119.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)

![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/fe43e17e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/7749ca9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/d13565a6.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. 

[](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Listing-True-Ski-In-Ski-Out-With-Private-Hot-Tub-Fire-Pit.h110896001.Hotel-Information)

Dover

10/10

Exceptional

(15 reviews)

"Beautiful house with everything we needed for a fun family vacation! The kids loved the bunk room. Todd was great to communicate with and made check in/check out super easy. Would stay again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer O.

[](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Listing-True-Ski-In-Ski-Out-With-Private-Hot-Tub-Fire-Pit.h110896001.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/111000000/110360000/110357800/110357764/45f9a18c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110360000/110357800/110357764/dc95d6ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/111000000/110360000/110357800/110357764/8db31977.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/111000000/110360000/110357800/110357764/ff2a9936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

[](https://www.expedia.ca/Jamaica-Hotels-Beautiful-Dog-Friendly-House-W-Fireplace.h110357764.Hotel-Information)

Mountain Acres

9.6/10

Exceptional

(4 reviews)

"We had an amazing time in Vermont and really enjoyed our stay. All of the bathrooms are updated and the home is clean and big. Rooms are separated giving privacy throughout. Thank you!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

[](https://www.expedia.ca/Jamaica-Hotels-Beautiful-Dog-Friendly-House-W-Fireplace.h110357764.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/12940d97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/ac3ab34e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/808e8825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/763a1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

[](https://www.expedia.ca/Whitingham-Hotels-Cozy-Lakeside-Tiny-Home.h74627282.Hotel-Information)

Whitingham

10/10

Exceptional

(50 reviews)

"Great stay perfect for 2 people, relax on then porch and look at the lake! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Keith D.

[](https://www.expedia.ca/Whitingham-Hotels-Cozy-Lakeside-Tiny-Home.h74627282.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/30000000/29640000/29634800/29634759/3b708b0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/30000000/29640000/29634800/29634759/a9164500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/30000000/29640000/29634800/29634759/b718d5ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29640000/29634800/29634759/2bfed2d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Six Bedroom Mountain Estate with Internet Access

[](https://www.expedia.ca/West-Dover-Hotels-Six-Bedroom-Mountain-Estate-With-Internet-Access.h29634759.Hotel-Information)

West Dover

9.6/10

Exceptional

(17 reviews)

"This house was great for a family gathering! It had a lot of space, has a great game room for the kids, is very clean and comfortable, and is close to Mt. Snow! It checked off all the boxes we were looking for-"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Steven Z.

[](https://www.expedia.ca/West-Dover-Hotels-Six-Bedroom-Mountain-Estate-With-Internet-Access.h29634759.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/01ff54d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/c8db5a9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/7e27ff2e.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)

### Lovely 2nd Floor Apartment

[](https://www.expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information)

Greenfield

10/10

Exceptional

(47 reviews)

"Close to downtown, clean & comfortable!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robbi C.

CA $161

CA $280 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89800000/89798000/89797974/ae6d1ba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video-game console, foosball](https://images.trvl-media.com/lodging/90000000/89800000/89798000/89797974/9b99a658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video-game console, foosball](https://images.trvl-media.com/lodging/90000000/89800000/89798000/89797974/61c7363e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89800000/89798000/89797974/126d4fb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bears Den Chalet | Ski Home Trail, Moover Shuttle, Outdoor Hot Tub!

[](https://www.expedia.ca/West-Dover-Hotels-Bears-Den-Chalet-On-Ski-Home-Trail-W-Ski-Shuttle.h89797974.Hotel-Information)

West Dover

10/10

Exceptional

(16 reviews)

"The house is located conveniently close to everything you need to enjoy the mountain and surrounding amenities. Perfectly laid out home to enjoy apres ski with family and friends."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert C.

[](https://www.expedia.ca/West-Dover-Hotels-Bears-Den-Chalet-On-Ski-Home-Trail-W-Ski-Shuttle.h89797974.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19820000/19812900/19812876/9d70fed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books, stereo](https://images.trvl-media.com/lodging/20000000/19820000/19812900/19812876/4077aec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books, stereo](https://images.trvl-media.com/lodging/20000000/19820000/19812900/19812876/01b71e7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books, stereo](https://images.trvl-media.com/lodging/20000000/19820000/19812900/19812876/6657d2c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakefront 3BR Log Cabin w/ Dock and Fire Pit

[](https://www.expedia.ca/Keene-Hotels-Waterfont-Log-Home-Nestled-In-The-Pines.h19812876.Hotel-Information)

Rindge

10/10

Exceptional

(56 reviews)

"Beautiful cabin with great views of the lake! The baseboard heat didnt work when we arrived but the woodstove worked perfectly and Alfred was very responsive in getting the baseboard fixed quickly"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John H.

[](https://www.expedia.ca/Keene-Hotels-Waterfont-Log-Home-Nestled-In-The-Pines.h19812876.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/f920340a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/feb8897d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/e3130fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/10545ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow

[](https://www.expedia.ca/West-Dover-Hotels-Game-Rm.h109380657.Hotel-Information)

Dover

9.0/10

Wonderful

(2 reviews)

"Weekend stay.Clean, comfortable, well equipped. Was as advertised.I would stay there again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Noah K.

[](https://www.expedia.ca/West-Dover-Hotels-Game-Rm.h109380657.Hotel-Information)

![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/003cdb7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/219c6425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/ad0c9f1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/6ae2121a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhome with patio & on-site pool, hot tub, sauna & tennis access

[](https://www.expedia.ca/Cavendish-Hotels-Townhome-With-Fireplace.h99947943.Hotel-Information)

Cavendish

9.4/10

Exceptional

(9 reviews)

"Had a great stay, I highly recommend "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeffrey M.

[](https://www.expedia.ca/Cavendish-Hotels-Townhome-With-Fireplace.h99947943.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/d3e8e7f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/9d2d9170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/26594765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/ab0e9adb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Carol - 10 minutes to Okemo & Newly Renovated

[](https://www.expedia.ca/Cavendish-Hotels-The-Carol-Styled-And-Freshly-Renovated-Stay10-Minutes-To-Okemo.h101895664.Hotel-Information)

Cavendish

10/10

Exceptional

(7 reviews)

"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Esther K.

[](https://www.expedia.ca/Cavendish-Hotels-The-Carol-Styled-And-Freshly-Renovated-Stay10-Minutes-To-Okemo.h101895664.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=2026-02-04&endDate=2026-02-05&regionId=553248635976430851&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Private vacation homes

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Apartments

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Condos

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America&regionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=CONDO)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America&regionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America&regionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=COTTAGE)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America&regionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=VILLA)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+County%2C+New+Hampshire%2C+United+States+of+America&regionId=553248635976430851&latLong=42.933597%2C-72.278426&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=CHALET)

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## Top Cheshire County Hotel Reviews

![Claremont Motor Lodge](https://images.trvl-media.com/lodging/39000000/38320000/38317200/38317142/64648cb7_y.jpg)

### Claremont Motor Lodge

10/10 Excellent

"Clean room,staff was super helpful, late night/early morning check in is easy would stay again!"

[](https://expedia.ca/Mount-Sunapee-Hotels-Claremont-Motor-Lodge.h38317142.Hotel-Information)

![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg)

### The Putney Inn

10/10 Excellent

"Clean, roomy, and has a mini fridge and microwave. Great for college kids going skiing! "

[](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information)

![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg)

### The Colonial Hotel

10/10 Excellent

"Amazing hotel and outstanding staff. Would absolutely stay here again."

[](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.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

"Everything/everyone was superb!!! "

[](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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

"Clean room nice area close to shopping and plenty of restaurants "

[](https://expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.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

"The staff is awesome there "

[](https://expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.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

"clean facilities marginal food choices"

[](https://expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.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

"Loved this hotel! Everything was as advertised. Only thing we were wishing for is a hot tub:)… maybe down the line?!"

[](https://expedia.ca/Newbury-Hotels-Hideaway-Inn-Mt-Snow.h120341253.Hotel-Information)

![Mount Snow Grand Summit Resort](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/57303655_y.jpg)

### Mount Snow Grand Summit Resort

10/10 Excellent

"Ski on skis off fantastic. Ski valet right on it "

[](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information)

## Find out more about Cheshire County

## Cheshire County Vacation Homes information

| Number of reviews | 825                |
| ----------------- | ------------------ |
| Accommodation     | 616 Vacation Homes |
| Lowest Price      | CA $280            |
| Highest Price     | CA $1,152          |

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- [Brentwood Golf Course ](https://www.expedia.ca/Brentwood-Golf-Course-Keene.d553248621556282420.Vacation-Attraction)
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