Title: Cheshire Vacation Rentals from $141: Search Short-Term Rentals | Expedia.com

[Cheshire Travel Guide](https://expedia.com/Cheshire.dx6005398)[Hotels in Cheshire](https://expedia.com/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Flights to Cheshire](https://expedia.com/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[Car Rentals in Cheshire](https://expedia.com/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.com/Cheshire.d6005398.Destination-Travel-Guides)

![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Cheshire vacation rentals

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/8168a5fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Williamstown

[](https://www.expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

8.8/10

Excellent

(2,294 reviews)

"Excellent location and terrific space and amenities."

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

Michelle

$126 nightly

$141 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/54590b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/411deb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Pittsfield

[](https://www.expedia.com/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information)

$277 nightly

$309 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039328/f24c9d86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039328/c125089e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039328/6adcd3b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039328/b2692a7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Shelburne Falls

[](https://www.expedia.com/Shelburne-Falls-Hotels-Rose-Room-Victorian-Home-Queen-Bed-Private-Bath.h120039328.Hotel-Information)

$173 nightly

$193 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Shelburne-Falls-Hotels-Rose-Room-Victorian-Home-Queen-Bed-Private-Bath.h120039328.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/30153bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/02d3bd96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/2c4a26d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/8d5d0ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Sand Lake

[](https://www.expedia.com/Sand-Lake-Hotels-Cabin-In-The-Woods.h101301745.Hotel-Information)

10/10

Exceptional

(14 reviews)

"Loved this cabin! The communal building is very clean & bathrooms are spotless. There is a farm stand near the entrance where you can buy firewood and fresh eggs. Trails are literally connected to the property for easy nature walks. We plan on coming back!"

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

Abby L.

$165 nightly

$183 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Sand-Lake-Hotels-Cabin-In-The-Woods.h101301745.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/eab00089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/3d81b129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/6cb471c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/296ae5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Whitingham

[](https://www.expedia.com/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information)

10/10

Exceptional

(14 reviews)

"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "

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

Jacklyn D.

$453 nightly

$507 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/bae121bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/69ce761a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/c5fd4f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/ffe021cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.com/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.Hotel-Information)

10/10

Exceptional

(5 reviews)

"It was great experience and we loved the ammenities."

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

Carrie C.

$207 nightly

$231 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow | Living area](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/1e2d02da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow | Private kitchen](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2d5c8478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/65ba1b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Camping in Williamstown

[](https://www.expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

9.4/10

Exceptional

(10 reviews)

"Healthy food too!"

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

GEORGINA

$145 nightly

$163 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c0b1b1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4d94624e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c1a3192b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4cd10809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Stephentown

[](https://www.expedia.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

$499 nightly

$554 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/dfd30b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/74627ad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/e51abd89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/c5241605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Williamstown

[](https://www.expedia.com/Williamstown-Hotels-2-Bdr-Apt-In-Town.h101733845.Hotel-Information)

9.6/10

Exceptional

(12 reviews)

"Clean, close to town, very convenient. On a busy road, so just be aware of that. But overall a good place to stay. "

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

Brian L.

$252 nightly

$283 total

Mar 13 - Mar 14

Total with taxes and fees

[](https://www.expedia.com/Williamstown-Hotels-2-Bdr-Apt-In-Town.h101733845.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w1024h599x0y41-cd278b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w1024h490x0y96-4fcb5611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w1024h497x0y96-d3ec142e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/4e9408e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Charlemont

[](https://www.expedia.com/Charlemont-Hotels-Bear-Creek-Cabin.h91621591.Hotel-Information)

10/10

Exceptional

(46 reviews)

"We enjoyed our stay!!"

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

Hillary S.

$423 nightly

$473 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Charlemont-Hotels-Bear-Creek-Cabin.h91621591.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/w4000h2662x0y5-f1ed56ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/4fb8018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/0ab9f2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/7d4bb1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Hinsdale

[](https://www.expedia.com/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

9.8/10

Exceptional

(36 reviews)

"Amazing, peaceful, immaculately clean property. "

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

Cec C.

$487 nightly

$544 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

![Gift shop](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/2e9623f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/w1333h900x16y0-bf275b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/a21be151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/ced4a56d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.com/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.Hotel-Information)

10/10

Exceptional

(5 reviews)

"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"

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

Jen B.

$207 nightly

$231 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/d4e277cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/3e8858f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, toaster](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/604150ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/2e432a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Stamford

[](https://www.expedia.com/Stamford-Hotels-Getaway-Near-Mass-MoCA.h89505416.Hotel-Information)

10/10

Exceptional

(29 reviews)

"We enjoyed our stay "

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

Lydia T.

$128 nightly

$143 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Stamford-Hotels-Getaway-Near-Mass-MoCA.h89505416.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/6c6cf45f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/5dc2bebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/972c3b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/12b81391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Florida

[](https://www.expedia.com/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information)

10/10

Exceptional

(4 reviews)

"Place was super clean. Beds were comfortable. Location was great."

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

Tristan e.

$318 nightly

$341 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w907h683x58y0-59aad182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w507h683x259y0-1d5f8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w524h683x260y0-f1656d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, printers](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w919h683x60y0-f3238385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Williamstown

[](https://www.expedia.com/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.Hotel-Information)

9.2/10

Wonderful

(24 reviews)

"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"

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

Carole S.

$402 nightly

$448 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.Hotel-Information)

![Gift shop](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/2b285fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/e60e5176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/78a1069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/d4a1d841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.com/Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Stayed one night at one of my favorite ski spots. Will be back again!"

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

Neil J.

$207 nightly

$231 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/9046d578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b86b4635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stockbridge

[](https://www.expedia.com/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

10/10

Exceptional

(34 reviews)

"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "

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

cathy c.

$494 nightly

$552 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/53935e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/751785ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/c3b9e910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/7239287a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Williamstown

[](https://www.expedia.com/Williamstown-Hotels-Downtown-Waterfront-Walk-To-Shops.h101733841.Hotel-Information)

10/10

Exceptional

(7 reviews)

"Perfect setup for anyone visiting Williamstown."

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

Michael P.

$257 nightly

$289 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Williamstown-Hotels-Downtown-Waterfront-Walk-To-Shops.h101733841.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/2f78aa12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/08591748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/20e7ddaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/04847bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Charlemont

[](https://www.expedia.com/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information)

$605 nightly

$653 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/5d56a155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/708e6bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/c1c12e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/539e07bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Charlemont

[](https://www.expedia.com/Charlemont-Hotels-12-Acre-Vacation-Rental-In-The-Berkshires.h98553938.Hotel-Information)

$515 nightly

$545 total

Mar 13 - Mar 14

Total with taxes and fees

[](https://www.expedia.com/Charlemont-Hotels-12-Acre-Vacation-Rental-In-The-Berkshires.h98553938.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.com/Hotel-Search?startDate=2026-03-24&endDate=2026-03-25&regionId=6005398&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

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Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America&regionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America&regionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America&regionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America&regionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America&regionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=VILLA)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America&regionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=CHALET)

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## Top Cheshire Hotel Reviews

![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0_y.jpg)

### Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"In the process of remodeling, but my room which was already renovated was very nice, as was the breakfast room. "

[](https://expedia.com/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"This was great. I did not really need the kitchen for my stay but for future planning this wil be great! Plenty of room in the living area. Bed was comfortable. Just beautiful "

[](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375_y.jpg)

### Vacation Village in the Berkshires

10/10 Excellent

"Great place in Williamstown. Near ski resort."

[](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"This place is okay. The view is stellar, but the hotel itself is average. It did the job. "

[](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"This area is really starting to build up. There is a small ski area. An Italian restaurant and 110 grill right on that road. About 15 min away Applebees. A lot of pizza and Mexican. Winter not only is there skiing there are a lot of snowmobile trails. Summer there are water falls you can see. Tubing you can do. The mountains are beautiful. Quiet and relaxing. "

[](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

6/10 Okay

"Hotel is going through a renovation which makes the place a little rougher than it’s used to be. No parking or limited parking at entrance of hotel. Valet parking personnel were parking cars on entrance round entrance and in the mourning, they were towing those cars from the property. Not a good look or feel for those staying there. Maybe in six months or a year down the line, hotel will come back to its glory. Today still needs lots of work. "

[](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

![Huttopia Berkshires ](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb_y.jpg)

### Huttopia Berkshires 

10/10 Excellent

"Excelente servicio "

[](https://expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"Room was awesome and very clean "

[](https://expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg)

### Hotel On North

10/10 Excellent

"Great one night experience, hotel was quiet and clean. Room was cozy and comfortable as well. Rate was very reasonable to make for a affordable ski trip"

[](https://expedia.com/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information)

## Find out more about Cheshire

**Everything you need to know about Cheshire vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheshire vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Cheshire vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Cheshire. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cheshire in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Cheshire rentals**

At Expedia, we put the best Cheshire vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cheshire rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheshire vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheshire. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
- All accommodation types in Cheshire

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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Cheshire ](https://expedia.com/Cheshire-Private-Vacation-Homes.d6005398-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Cheshire ](https://expedia.com/Cheshire-Apartments.d6005398-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Cheshire ](https://expedia.com/Cheshire-Cottages.d6005398-aaCottages.Travel-Guide-Accommodation)
- [Condo Rentals in Cheshire ](https://expedia.com/Cheshire-Condos.d6005398-aaCondos.Travel-Guide-Accommodation)
- [B&B in Cheshire ](https://expedia.com/Cheshire-Bed-And-Breakfast.d6005398-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Resorts in Cheshire ](https://expedia.com/Cheshire-Resorts.d6005398-aaResorts.Travel-Guide-Accommodation)
- [Cabin Rentals in Cheshire ](https://expedia.com/Cheshire-Cabins.d6005398-aaCabins.Travel-Guide-Accommodation)
- [Motels in Cheshire ](https://expedia.com/Cheshire-Motels.d6005398-aaMotels.Travel-Guide-Accommodation)
- [Farmstay in Cheshire ](https://expedia.com/Cheshire-Agritourism.d6005398-aaAgritourism.Travel-Guide-Accommodation)
- [Guest Houses in Cheshire ](https://expedia.com/Cheshire-Guest-Houses.d6005398-aaGuestHouses.Travel-Guide-Accommodation)
- [Chalets in Cheshire ](https://expedia.com/Cheshire-Chalets.d6005398-aaChalets.Travel-Guide-Accommodation)
- [Inns in Cheshire ](https://expedia.com/Cheshire-Inns.d6005398-aaInns.Travel-Guide-Accommodation)
- [Lodges in Cheshire ](https://expedia.com/Cheshire-Lodges.d6005398-aaLodges.Travel-Guide-Accommodation)
- [Aparthotels in Cheshire ](https://expedia.com/Cheshire-Apart-Hotels.d6005398-aaApartHotels.Travel-Guide-Accommodation)
- [Villas in Cheshire ](https://expedia.com/Cheshire-Villas.d6005398-aaVillas.Travel-Guide-Accommodation)
- [Condo Resorts in Cheshire ](https://expedia.com/Cheshire-Condominium-Resort.d6005398-aaCondominiumResort.Travel-Guide-Accommodation)
- [RV Parks in Cheshire ](https://expedia.com/Cheshire-RV-Parks.d6005398-aaRVParks.Travel-Guide-Accommodation)
- [Castles in Cheshire ](https://expedia.com/Cheshire-Castles.d6005398-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Cheshire?

### What's the top vacation rental that Cheshire has to offer?

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### What can I see and do in Cheshire?

### What are vacation rentals like in Cheshire?

### Expedia's Latest Trends

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- [Hotels in Amherst](https://expedia.com/Amherst-Hotels.d5948.Travel-Guide-Hotels)
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- [Hotels in Falmouth](https://expedia.com/Falmouth-Hotels.d7287.Travel-Guide-Hotels)
- [Hotels in Worcester](https://expedia.com/Worcester-Hotels.d6023336.Travel-Guide-Hotels)
- [Hotels in Marlborough](https://expedia.com/Marlborough-Hotels.d8869.Travel-Guide-Hotels)
- [Hotels in Lenox](https://expedia.com/Lenox-Hotels.d8587.Travel-Guide-Hotels)
- [Hotels in Gloucester](https://expedia.com/Gloucester-Hotels.d8008.Travel-Guide-Hotels)
- [Hotels in New Bedford](https://expedia.com/New-Bedford-Hotels.d1180.Travel-Guide-Hotels)

Cars

- [Car rentals in Mansfield](https://expedia.com/Car-Rentals-In-Mansfield.d8456.Car-Rental-Guide)
- [Car rentals in Springfield](https://expedia.com/Car-Rentals-In-Springfield.d6047669.Car-Rental-Guide)
- [Car rentals in Worcester](https://expedia.com/Car-Rentals-In-Worcester.d6023336.Car-Rental-Guide)

Activities

- [Things to do in Hyannis](https://expedia.com/Things-To-Do-In-Hyannis.d1544.Travel-Guide-Activities)

Packages

- [Nantucket Vacation](https://expedia.com/Nantucket.d285.Destination-Travel-Guides)

Vacation Rentals

- [Nantucket Vacation Rentals](https://expedia.com/Nantucket-Vacation-Rentals.d285.Travel-Guide-VacationRentals)

General

- [Visit Manchester-by-the-Sea](https://expedia.com/Manchester-By-The-Sea.dx129363)
- [Visit Rockport](https://expedia.com/Rockport.dx6350)

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