Title: Cheshire Vacation Rentals from $143: 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 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6005398&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 two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-06-26&endDate=2026-06-28&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/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)

![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)

![Interior](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/2650ddba.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

(13 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 5 - Mar 6

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/90000000/89510000/89505500/89505416/d4e277cc.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)

![Dining](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/31ffedca.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)

### 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 4 - Mar 5

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/9832d1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/76bef906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/6d3522c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/6c18250e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Shelburne Falls

[](https://www.expedia.com/Shelburne-Falls-Hotels-2-Twin-Beds-On-1st-Floor-With-En-Suite-Bathroom.h120039334.Hotel-Information)

$161 nightly

$180 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Shelburne-Falls-Hotels-2-Twin-Beds-On-1st-Floor-With-En-Suite-Bathroom.h120039334.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)

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/972c3b08.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)

### 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 4 - Mar 5

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/5619200c.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)

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/c3b9e910.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 4 - Mar 5

Total with taxes and fees

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/516bcaba.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)

### 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.

$469 nightly

$525 total

Mar 10 - Mar 11

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)

![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/0ac89dfb.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.

$223 nightly

$249 total

Mar 9 - Mar 10

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 detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.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)

![TV](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/3bbdf637.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 4 - Mar 5

Total with taxes and fees

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

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/26d89405.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)

![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)

### 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.

$249 nightly

$280 total

Mar 5 - Mar 6

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/a0f802bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/a133e616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/0e4076ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sherwood Forest

[](https://www.expedia.com/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

10/10

Exceptional

(5 reviews)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

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

Sharon K.

$351 nightly

$392 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.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 4 - Mar 5

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)

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

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/09a3de30.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)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/08591748.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 4 - Mar 5

Total with taxes and fees

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

![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)

![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)

![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 4 - Mar 5

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/f020a98b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/d0b6023a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/0fb5f28d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/4c69da5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Williamstown

[](https://www.expedia.com/Williamstown-Hotels-New-Studio-In-Town.h45471406.Hotel-Information)

10/10

Exceptional

(10 reviews)

"Great location, we really enjoyed our stay! "

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

Lydia J.

$240 nightly

$270 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Williamstown-Hotels-New-Studio-In-Town.h45471406.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/f305b62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/597105fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/d80b29aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/037efde9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Charlemont

[](https://www.expedia.com/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Very nice house and the stay was unproblematic!"

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

Noah K.

$395 nightly

$441 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/a7eb284a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/d5a96942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/cc0a8ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/2435c38a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Stephentown

[](https://www.expedia.com/Stephentown-Hotels-2-Bed-Berkshire-Apt-Minutes-To-Jiminy-Peak-Ski.h64428459.Hotel-Information)

8.4/10

Very Good

(12 reviews)

"Great location and property. thank you"

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

Christine P.

$242 nightly

$258 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Stephentown-Hotels-2-Bed-Berkshire-Apt-Minutes-To-Jiminy-Peak-Ski.h64428459.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)

![Indoor pool](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/d4a1d841.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)

### 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 4 - Mar 5

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/91000000/90190000/90182200/90182167/70501210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/w1333h900x16y0-62588f79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/27b1a758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/w515h679x0y4-9a7cc624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.com/Hancock-Hotels-Must-See-Cabin-Suite-Jiminy-Sleeps-4-Mountainview-Ski-OnOff-Country-Inn-Redone.h90182167.Hotel-Information)

10/10

Exceptional

(11 reviews)

"Room was perfect location for skiing. Able to see slopes and a few of the chairlifts from room. Beds were super comfortable. Parking was close by and in private area which helped avoid parking in huge resort parking lot. Owner was very responsive."

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

Charles

$207 nightly

$231 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Hancock-Hotels-Must-See-Cabin-Suite-Jiminy-Sleeps-4-Mountainview-Ski-OnOff-Country-Inn-Redone.h90182167.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) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4cd10809.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/123000000/122170000/122165500/122165421/0800588d.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 4 - Mar 5

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)

![Exterior](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/6b5af50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/00cc85e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/06261f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in New Lebanon

[](https://www.expedia.com/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

9.4/10

Exceptional

(26 reviews)

"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."

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

Paul S.

$310 nightly

$347 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.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=2026-03-17&endDate=2026-03-18&regionId=6005398&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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## Find vacation rentals that suit your style

Cabins

[](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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CABIN)

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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=COTTAGE)

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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VACATION_HOME)

Aparthotels

[](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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APART_HOTEL)

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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CHALET)

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## Top Cheshire Hotel Reviews

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg)

### Vacation Village in the Berkshires

10/10 Excellent

"Comfortable room with lots of space and easy access to skiing. I needed a baking tray for dinner one night and they were able to provide a baking tray for "

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

"Room is attractive and clean and the staff is always welcoming. Back rooms, where we stay, are quiet and look out across a marsh to the mountain."

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

10/10 Excellent

"Room was spotless, staff was very kind!"

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

![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046_y.jpg)

### Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Clean, friendly staff, quiet, great breakfast, easy to get anywhere locally, updated!"

[](https://expedia.com/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information)

![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg)

### The Williams Inn

10/10 Excellent

"nice aesthetics"

[](https://expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information)

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

### Berkshire Mountain Lodge

10/10 Excellent

"Overall pleasant stay; great facilities, staff, and location"

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

![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg)

### Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"What a great place! Really gracious staff and good food."

[](https://expedia.com/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.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

"Very spacious and comfortable. Great for families."

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

![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg)

### The Porches Inn at Mass MoCA

10/10 Excellent

"Excellent "

[](https://expedia.com/North-Adams-Hotels-The-Porches-Inn.h7662392.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 $143 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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- [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 West Springfield](https://expedia.com/West-Springfield-Hotels.d7738.Travel-Guide-Hotels)
- [Hotels in Rockport](https://expedia.com/Rockport-Hotels.d6350.Travel-Guide-Hotels)
- [Hotels in Northampton](https://expedia.com/Northampton-Hotels.d9187.Travel-Guide-Hotels)
- [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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