Title: Cheshire Apartment Rentals from CA $198 | Expedia.ca

[Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/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)

# Search Apartment Rentals in Cheshire

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## Check prices for these dates

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Cheshire apartments

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

![TV](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/64c44465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/69466e24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/76b0f7ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Stamford

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

10/10

Exceptional

(28)

"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."

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

Mario R.

CA $94

CA $198 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/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)

![Living area](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/403e3f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/95c4fcb6.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.ca/Shelburne-Falls-Hotels-2-Twin-Beds-On-1st-Floor-With-En-Suite-Bathroom.h120039334.Hotel-Information)

CA $91

CA $208 total

includes taxes & fees

Jan 12 - Jan 13, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/c3b6bbdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/9c369939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/c3d91b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/b3464458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lanesborough

[](https://www.expedia.ca/Lanesborough-Hotels-Cozy-Rustic-Apt-In-18th-C-Berkshire-Farmhouse.h73728934.Hotel-Information)

9.6/10

Exceptional

(67)

"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"

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

Janice L.

CA $186

CA $283 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Lanesborough-Hotels-Cozy-Rustic-Apt-In-18th-C-Berkshire-Farmhouse.h73728934.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/250d56fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/0ac89dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

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

10/10

Exceptional

(5)

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

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

Carrie C.

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/feda3681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/408e3ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/14ef20fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/9c2c97d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Stephentown

[](https://www.expedia.ca/Stephentown-Hotels-Berkshires-Apartment-At-The-Stephentown-Hotel.h100959022.Hotel-Information)

10/10

Exceptional

(3)

"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."

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

Matt E.

CA $133

CA $288 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Stephentown-Hotels-Berkshires-Apartment-At-The-Stephentown-Hotel.h100959022.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)

![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)

![TV, DVD player](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/32688657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/739b3363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

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

10/10

Exceptional

(8)

"We had a wonderful 3 day weekend! Perfect location for families."

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

Eric B.

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

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

![TV, DVD player, books](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/b31564d8.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)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/56cd6111.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)

### Apartment in Hancock

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

10/10

Exceptional

(3)

"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.

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

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

![1 bedroom, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/a0875211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/185f4743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/edf0cab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/4ee3217b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Adams

[](https://www.expedia.ca/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.Hotel-Information)

9.6/10

Exceptional

(13)

"Adams is a beautiful town and looks and feels like the appalachian trail! "

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

judy r.

CA $160

CA $337 total

includes taxes & fees

Dec 23 - Dec 24

[](https://www.expedia.ca/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9c846f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9abb62fb_edited_7b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/2a4ba750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/a110f773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.ca/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.Hotel-Information)

10/10

Exceptional

(23)

"This property is spacious, clean and well- appointed. I would stay here again!"

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

Amanda M.

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/b5482417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/3663d99c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/9e312028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/w905h678x0y5-7353a588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.ca/Hancock-Hotels-Disney-Magic-At-Jiminy-Must-See-Gorgeous-Sleeps-4.h78537603.Hotel-Information)

9.8/10

Exceptional

(18)

"We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip."

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

Allison V.

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hancock-Hotels-Disney-Magic-At-Jiminy-Must-See-Gorgeous-Sleeps-4.h78537603.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/949e9107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/78da5d01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/97765f2f_edited_8669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/643b3865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.ca/Hancock-Hotels-Chic-2BR-Suite-On-Jiminy-Mtn-Sleeps-8-Gorgeous.h76713290.Hotel-Information)

9.6/10

Exceptional

(30)

"Great and clean property! Very easy to access and good parking too."

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

Todd A.

CA $218

CA $448 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hancock-Hotels-Chic-2BR-Suite-On-Jiminy-Mtn-Sleeps-8-Gorgeous.h76713290.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/5bbd846e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/6d462fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/f021085a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/d791261d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Shelburne Falls

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Rose-Wisteria-4-Guests-2-Bedrooms-Fullqueen-Beds.h120039338.Hotel-Information)

CA $174

CA $344 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Rose-Wisteria-4-Guests-2-Bedrooms-Fullqueen-Beds.h120039338.Hotel-Information)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109420000/109415600/109415543/1b2bd489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109420000/109415600/109415543/30c487a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109420000/109415600/109415543/a0995ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109420000/109415600/109415543/c659fbe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Whitingham

[](https://www.expedia.ca/Whitingham-Hotels-Amazing-34-Foot-High-Shipping-Container-Home-In-Whitingham-On-Sadawga-Lake.h109415543.Hotel-Information)

10/10

Exceptional

(2)

"as advertised."

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

Joshua G.

CA $601

CA $1,025 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Whitingham-Hotels-Amazing-34-Foot-High-Shipping-Container-Home-In-Whitingham-On-Sadawga-Lake.h109415543.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120670000/120662100/120662087/e729958e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/121000000/120670000/120662100/120662087/8ffc6379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120670000/120662100/120662087/eabcfd71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120670000/120662100/120662087/d565c872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in North Adams

[](https://www.expedia.ca/North-Adams-Hotels-The-Allen-House-Historic-North-Adams-Home-In-The-Berkshire-Mountains.h120662087.Hotel-Information)

CA $241

CA $420 total

includes taxes & fees

Jan 15 - Jan 16, 2026

[](https://www.expedia.ca/North-Adams-Hotels-The-Allen-House-Historic-North-Adams-Home-In-The-Berkshire-Mountains.h120662087.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/101430000/101424500/101424483/d4b659d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/102000000/101430000/101424500/101424483/f4cf1bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books](https://images.trvl-media.com/lodging/102000000/101430000/101424500/101424483/8007a16f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/102000000/101430000/101424500/101424483/c5ae2be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.ca/Hancock-Hotels-Deluxe-Mountain-Fox-Suite-Jiminy-Peak-Ski-On-Off-Fully-Redone-Decor.h101424483.Hotel-Information)

10/10

Exceptional

(1)

"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."

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

Antonio S.

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hancock-Hotels-Deluxe-Mountain-Fox-Suite-Jiminy-Peak-Ski-On-Off-Fully-Redone-Decor.h101424483.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/17e920ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/788e1637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/44b79f2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/e067dc85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Stephentown

[](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Getaway-Stephentown-Hotel.h95668997.Hotel-Information)

10/10

Exceptional

(5)

"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."

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

elizabeth r.

CA $243

CA $441 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Getaway-Stephentown-Hotel.h95668997.Hotel-Information)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/w1276h853x4y0-c61fbb4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/6932c0b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/e78a64be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/94c93760.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lanesborough

[](https://www.expedia.ca/Lanesborough-Hotels-Charming-Apt-In-18th-C-Berkshire-Farmhouse.h87818778.Hotel-Information)

9.4/10

Exceptional

(40)

"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."

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

Roy

CA $186

CA $283 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Lanesborough-Hotels-Charming-Apt-In-18th-C-Berkshire-Farmhouse.h87818778.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/73af4ec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/67dfe3b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gift shop](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/7fffcbcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/ac7da18c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.ca/Hancock-Hotels-Game-Night-Suite-At-Jiminy-Peak-Ski-OnOff-Sleeps-4.h111728387.Hotel-Information)

10/10

Exceptional

(3)

"Great room decorations, travel with two kids they have a great time playing video games"

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

Andres

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hancock-Hotels-Game-Night-Suite-At-Jiminy-Peak-Ski-OnOff-Sleeps-4.h111728387.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/3b948672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/w992h667x8y0-e5344523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/w1298h680x0y0-b31746a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, offices](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/fe1becd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.ca/Hancock-Hotels-1st-FL-Mtn-View-Woodland-Suite-On-Jiminy-Sleeps-4-Ski-OnOff.h90786765.Hotel-Information)

9.4/10

Exceptional

(6)

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hancock-Hotels-1st-FL-Mtn-View-Woodland-Suite-On-Jiminy-Sleeps-4-Ski-OnOff.h90786765.Hotel-Information)

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

![TV, DVD player, books](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/e6135e47.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/97000000/96840000/96837300/96837232/141e4e93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

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

10/10

Exceptional

(3)

"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.

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

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

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-30&endDate=2025-12-31&regionId=6005398&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Condos

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Aparthotels

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Cottages

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America&regionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=VILLA)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America&regionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=CHALET)

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## Top Cheshire Hotel Reviews

![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 is a wonderful place to stay. The breakfast is delicious. The pool and hot tub are delightful. The staff are like family. "

[](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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/e153ce9c_y.jpg)

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

10/10 Excellent

"Very clean. Nice amenities. Had everything you needed. "

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

![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg)

### The Red Lion Inn

10/10 Excellent

"We had a very nice experience staying at the Red Lion Inn. Our room was upgraded when checking in which was a nice surprise. The hotel was beautifully decorated for the season. We loved the cozy feel of the fireplace in the lobby especially on such a cold day. "

[](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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

"Hot tub was relaxing. Parking was easy. Restaurant within walking distance. If you forget anything dollar general close."

[](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information)

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg)

### Berkshires Untold

10/10 Excellent

"Lovely little elegant hotel. Beautiful well appointed rooms. Comfortable bed. Reasonably price. Great find. "

[](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Nice room"

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

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg)

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

10/10 Excellent

"Really quiet, peaceful stay and beautiful spot for the money. Front desk staff so nice. No elevator to second floor so keep in mind if have accessibility issues/wheelchair user. Great view and gluten free menu options. Would stay again if in area. Was just passing through on way to medical appointment. "

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

![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg)

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

10/10 Excellent

"Comfortable, quiet, clean, great breakfast "

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information)

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

### The Williams Inn

10/10 Excellent

"Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick. "

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

## Find out more about Cheshire

## Cheshire Apartments information

| Number of reviews | 228            |
| ----------------- | -------------- |
| Accommodation     | 102 Apartments |
| Lowest Price      | CA $198        |
| Highest Price     | CA $1,025      |

## Frequently asked questions

### What's it like to stay at an apartment in Cheshire?

### How do you know if an apartment is a good option for you?

### What's a favorite apartment for a stay in Cheshire?

### What can I expect from the weather during my trip to Cheshire?

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

### What's the best way to get to and around Cheshire?

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