Title: Book The Best Hotels in Cheshire, MA for 2026 from CA $98 - Fully Refundable Options - Expedia.ca

 

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![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/northeast-usa-fall-foliage-lake-mountain-scenic-view.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find hotels in Cheshire, MA from CA $98

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## Go beyond your typical stay in Cheshire

Cabin

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&lodging=CABIN)

Pool

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&amenities=POOL)

Family friendly

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&travelerType=family_friendly)

Hot tub

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&amenities=HOT_TUB)

Pet friendly

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&amenities=PETS)

Farm

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&lodging=AGRITOURISM)

Apart­ment

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&lodging=APARTMENT)

Condo

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&lodging=CONDO)

Cottage

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&lodging=COTTAGE)

## Check prices for these dates

Tonight

[Nov 30 - Dec 1](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-30&endDate=2025-12-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-12-01&endDate=2025-12-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 988 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, Private Bathroom (Field of Dreams)](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/d973dbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harbour House Inn

Cheshire

9.4/10

Exceptional

(53)

"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "

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

Lorie

CA $337

CA $357 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/4fd790fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Lee

9.0/10

Wonderful

(1006)

"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"

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

Elisabeth

CA $137

CA $153 total

includes taxes & fees

Dec 21 - Dec 22

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

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Yankee, Trademark Collection by Wyndham

Lenox

9.2/10

Wonderful

(1013)

"Great stay!"

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

Ann

CA $88

CA $98 total

includes taxes & fees

Dec 14 - Dec 15

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

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

![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.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)

### Vacation Village in the Berkshires

Williamstown

8.8/10

Excellent

(2157)

"Great place!"

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

Nicole

CA $114

CA $143 total

includes taxes & fees

Dec 2 - Dec 3

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

![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Untold

Lenox

9.0/10

Wonderful

(806)

"We had a nice room and the food was delicious. Great place to stay. "

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

Vincent

CA $153

CA $171 total

includes taxes & fees

Dec 2 - Dec 3

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

![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Pittsfield

8.0/10

Very good

(975)

"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"

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

Frank

CA $130

CA $145 total

includes taxes & fees

Dec 3 - Dec 4

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

![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/0fe63f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/3c0625c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

South Lee

9.0/10

Wonderful

(792)

"Place was great!"

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

Benjamin

CA $149

CA $186 total

includes taxes & fees

Dec 8 - Dec 9

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

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/9b7b4cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Red Lion Inn

Stockbridge

8.8/10

Excellent

(1003)

"I love the ambience - historic and comfortable and excellent food. "

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

Nancy

CA $210

CA $297 total

includes taxes & fees

Dec 16 - Dec 17

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

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/67e1adab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/617da859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/a89bc327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Pittsfield

9.2/10

Wonderful

(64)

"Very clean room, courteous staff. "

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

Jeffrey

CA $133

CA $149 total

includes taxes & fees

Dec 7 - Dec 8

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

![Front of property](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/f3a87415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sundeck](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a02c1cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/d32c867e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cornell Inn, Lenox & The Berkshires

Lenox

9.0/10

Wonderful

(1004)

"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."

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

Jacob

CA $198

CA $276 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information)

![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/5e762248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/9903b094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 6:00 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/41222353.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Downstreet, an Ascend Collection Hotel

North Adams

8.8/10

Excellent

(1012)

"Staff was very nice!"

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

David

CA $150

CA $167 total

includes taxes & fees

Dec 20 - Dec 21

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

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/f450d89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/b51475ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/670699cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Mountain Lodge

Pittsfield

9.0/10

Wonderful

(776)

"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"

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

Michelle

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/3ef861f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/651f878e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel On North

Pittsfield

9.6/10

Exceptional

(801)

"Clean room and staff was super friendly"

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

Yuen

CA $186

CA $208 total

includes taxes & fees

Dec 22 - Dec 23

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

![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/4417504a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Extended Stay)](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/c71b3d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room (Superior King Bed with a Porch)](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/aaec0515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Porches Inn at Mass MoCA

North Adams

9.4/10

Exceptional

(444)

"It is the perfect place to stay!"

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

Darrell

CA $213

CA $269 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/8666c376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

8.6/10

Excellent

(1004)

"I have stayed here many times and it is consistently a comfortable, clean and quiet place."

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

Jeanine

CA $131

CA $146 total

includes taxes & fees

Dec 3 - Dec 4

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

![Front of property](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/bb8fdf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/3d2d74c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fire Spa Suite | Room amenity](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/af4baaa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fire Spa Suite](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/de897732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chambery Inn

Lee

9.6/10

Exceptional

(373)

"Amazing customer service! Location was very good to explore the area."

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

Sophia

[](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/1ea731f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/c60f19d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Williams Inn

Williamstown

9.6/10

Exceptional

(546)

"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"

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

Jon

CA $275

CA $308 total

includes taxes & fees

Dec 8 - Dec 9

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

![Exterior](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5d49dcf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/dd484194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5e45920f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/adb513b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Williamstown

Williamstown

8.8/10

Excellent

(394)

"our stay was great."

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

nathaniel

CA $200

CA $223 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/w4000h2033x0y0-e62570a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/cbf141ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/ccde32c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Lenox Berkshires

Lenox

9.2/10

Wonderful

(588)

"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "

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

Mingming

CA $189

CA $211 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/45e111cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/568a1b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/6203d3bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/2c0ca8ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Villager Motel

Williamstown

8.8/10

Excellent

(763)

"It's very good for stay over"

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

Frances

CA $96

CA $108 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Williamstown-Hotels-The-Villager-Motel.h2832172.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=2025-12-15&endDate=2025-12-16&regionId=6005398&adults=2&sort=RECOMMENDED&openPlayBack=true)

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Save an average of 15% on thousands of hotels when you're signed in

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## 

Black Friday Sale

Limited-time deals: save up to 50% on select hotels

[Book now](https://expedia.ca/deals?rfrr=HTG_BF_PROMO_6005398)

## Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and local cuisine.

[See all hotels in Cheshire](https://www.expedia.ca/Hotel-Search?startDate=2025-12-15&endDate=2025-12-16&adults=2&regionId=6005398)

![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=900&h=599&p=1&q=high)

### Stay near popular Cheshire attractions

[](https://expedia.ca/St-Marys-Of-The-Assumption-Church-Hotels.0-l553248621532665539-0.Travel-Guide-Filter-Hotels)

#### St Mary's of the Assumption Church

St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views, or seek out its ski slopes.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532665539)

## More cheap stays in Cheshire

![Quality Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn

170 Housatonic Street Lee MA

CA $130

CA $145 total

Dec 14 - Dec 15

includes taxes & fees

8.2/10 Very Good! (1,002 reviews)

[](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

CA $88

CA $98 total

Dec 14 - Dec 15

includes taxes & fees

9/10 Wonderful! (1,011 reviews)

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

![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

CA $110

CA $123 total

Dec 2 - Dec 3

includes taxes & fees

7.4/10 Good! (824 reviews)

[](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information)

![Fairfield Inn & Suites by Marriott Williamstown](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5d49dcf2_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Fairfield Inn & Suites by Marriott Williamstown

430 Main St Williamstown MA

CA $200

CA $223 total

Dec 14 - Dec 15

includes taxes & fees

8.8/10 Excellent! (392 reviews)

[](https://expedia.ca/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information)

![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd Lenox MA

CA $155

CA $174 total

Dec 7 - Dec 8

includes taxes & fees

9/10 Wonderful! (1,002 reviews)

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

![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

CA $131

CA $146 total

Dec 3 - Dec 4

includes taxes & fees

8.4/10 Very Good! (1,002 reviews)

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

## Hotels in Cheshire with star-rating

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

11 properties

[](https://expedia.ca/4Star-Cheshire-Hotels.s40-0-d6005398.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

108 properties

[](https://expedia.ca/3Star-Cheshire-Hotels.s30-0-d6005398.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

101 properties

[](https://expedia.ca/2Star-Cheshire-Hotels.s20-0-d6005398.Travel-Guide-Filter-Hotels)

## Find out more about Cheshire

### Top reasons to visit Cheshire

-   **Outdoor Adventures:** Cheshire is a haven for outdoor enthusiasts, featuring excellent skiing and scenic hiking opportunities.
-   **Charming Local Culture:** Explore the quaint Cheshire Village and visit the Cheshire Military Museum for a taste of local history.
-   **Vibrant Nightlife:** Unwind at various pubs and local theatres after a day of adventure.
-   **Beautiful Scenery:** Enjoy the picturesque landscapes and scenic mountains that surround the area.
-   **Diverse Accommodations:** Find a range of hotels and resorts catering to families, couples, and adventurers alike.

### Find great hotels near Cheshire

Discover the charm of Cheshire, Massachusetts, where a variety of hotels and resorts await to enhance your stay. Whether you’re seeking a family-friendly retreat, a romantic getaway, or an adventure-filled vacation, Cheshire offers accommodations that cater to all your needs. Explore the best Cheshire hotels for a memorable experience, and find the perfect spot to unwind while enjoying the scenic beauty of this delightful town.

-   **[Holiday Inn & Suites Pittsfield-Berkshires by IHG:](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)** Nestled in the heart of Pittsfield, only 14.5km from Cheshire, this 3-star hotel is perfect for families and adventure seekers alike. The property boasts a range of outdoor activities such as snowboarding, hiking, horseback riding, and fishing, making it an excellent choice for those looking to embrace the great outdoors. Families will appreciate the child-friendly amenities, including free cribs and window guards for safety. With its city-themed atmosphere and recreational options nearby, this hotel promises a memorable stay filled with excitement and exploration.
-   **[Club Wyndham Bentley Brook:](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information)** Situated just 9.7km from Cheshire, Club Wyndham Bentley Brook is a 3-star resort tailored for ski enthusiasts and adventure lovers. With convenient access to ski shuttles and lifts, guests can hit the slopes in no time. The property features onsite snowboarding and is near hiking and downhill skiing locations, making it an ideal retreat for winter sports enthusiasts. Enjoy the inviting atmosphere and easy access to thrilling outdoor activities that will satisfy your adventurous spirit.
-   **Hotel Downstreet, Ascend Hotel Collection:** Located 16.1km from Cheshire, Hotel Downstreet is a welcoming 3-star hotel that embraces inclusivity and pet-friendly policies. Ideal for LGBTQIA travellers, the property is affiliated with LGBTQI travel guides and allows pets, ensuring everyone feels at home. With amenities catering to dogs and cats, guests can enjoy their stay without leaving their furry friends behind. This hotel blends comfort and community, making it a great choice for those seeking a warm and welcoming atmosphere.

### Where to stay near Cheshire

Cheshire, Massachusetts, offers a delightful blend of adventure and family-friendly experiences, making it an ideal vacation spot. From picturesque locations perfect for weekend getaways to romantic escapes, visitors can explore charming neighborhoods nearby. Enjoy skiing and outdoor activities while soaking in the scenic beauty. With convenient access to lovely locations, Cheshire provides a memorable atmosphere for every type of traveller, whether you're seeking adventure or a peaceful retreat.

-   **[Williamstown:](https://www.expedia.ca/Williamstown-Hotels.d7859.Travel-Guide-Hotels)** Nestled 17.7km from Cheshire, Williamstown is a charming city renowned for its vibrant arts scene, historic college university, and stunning natural landscapes. Visitors flock here year-round, with peak seasons in April and June to July, drawn by the allure of skiing and adventure sports. The nearby ski fields and resorts offer excellent winter activities, while the picturesque mountains and tranquil lake provide a perfect backdrop for outdoor exploration. Whether you're hitting the slopes or strolling through the town's cultural landmarks, Williamstown promises a delightful travel experience.
-   **[Pittsfield:](https://www.expedia.ca/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)** Located just 14.5km from Cheshire, Pittsfield is a dynamic city that comes alive during peak summer months from June to August. Known for its adventurous spirit, this city offers ample opportunities for skiing, as well as access to a stunning lake and mountain scenery. The local waterpark adds an extra element of fun for families, making it a versatile destination for travellers. With its rich history and community events, Pittsfield provides a warm and welcoming atmosphere, perfect for anyone looking to immerse themselves in local culture while enjoying the great outdoors.
-   **[North Adams:](https://www.expedia.ca/North-Adams-Hotels.d9137.Travel-Guide-Hotels)** Just 16.1km away from Cheshire, North Adams is a vibrant city that embraces adventure and creativity. Known for its thriving arts community, this city features a renowned art museum and numerous public art installations that invite exploration. With peak visitor numbers in June to July and September, North Adams attracts those seeking outdoor fun and skiing experiences. The surrounding mountains provide fantastic hiking opportunities, while the cultural centre fosters a lively environment for arts and entertainment. North Adams offers a unique blend of nature and culture, ensuring an unforgettable vacation experience.

### Things to do near Cheshire

Cheshire, Massachusetts, is perfect for outdoor enthusiasts and adventure seekers, offering fantastic skiing opportunities at its local ski resorts and fields. Visitors can enjoy scenic walks, vibrant nightlife, and a variety of pubs to unwind after a day on the slopes. For those looking to relax, the area also features charming local theatres and championship golf courses, making it an ideal destination for a well-rounded vacation experience.

**Shopping**

Cheshire offers a quaint shopping experience with local charm. For a broader selection, head to the North Adams Center, North Adams Gateway Center, or Colonial Plaza, all located 16.1km away, featuring a mix of business and family vibes. If you're up for a drive, you'll find more unique shops along the way.

**Recreation**

[Skyline Country Club](https://www.expedia.ca/Skyline-Country-Club-Hotels.0-l553248621532665295-0.Travel-Guide-Filter-Hotels) offers a scenic golf experience with stunning views and outdoor sports activities, perfect for golf enthusiasts. For a more tranquil atmosphere, visit [Windsor Lake Park](https://www.expedia.ca/Windsor-Lake-Park-Hotels.0-l553248621560926712-0.Travel-Guide-Filter-Hotels), where you can unwind amidst nature and enjoy wellness-focused relaxation. [Waubeeka Golf Links](https://www.expedia.ca/Waubeeka-Golf-Links-Hotels.0-l553248621561173643-0.Travel-Guide-Filter-Hotels) also provides an excellent golfing experience surrounded by beautiful landscapes.

**Adventure**

At [Jiminy Peak Mountain Resort](https://www.expedia.ca/Jiminy-Peak-Mountain-Resort-Hotels.0-l553248621532665536-0.Travel-Guide-Filter-Hotels), experience thrilling skiing and winter sports vibes only 11.3km from Cheshire. At [Berkshire East Ski Resort](https://www.expedia.ca/Berkshire-East-Ski-Resort-Hotels.0-l553248621532666707-0.Travel-Guide-Filter-Hotels), 24.1km away, enjoy outdoor adventures amidst breathtaking scenery. For hiking enthusiasts, the [Skyline Trail](https://www.expedia.ca/Skyline-Trail-Hotels.0-l553248621532666608-0.Travel-Guide-Filter-Hotels), also 24.1km from Cheshire, offers stunning views and a true adventure experience.

**Nightlife**

Experience the vibrant nightlife in Cheshire by attending a show at the [Williamstown Theatre Festival](https://www.expedia.ca/Williamstown-Theatre-Festival-Hotels.0-l553248621532665542-0.Travel-Guide-Filter-Hotels) or the [Adams Theater](https://www.expedia.ca/Adams-Theater-Hotels.0-l811533410309558272-0.Travel-Guide-Filter-Hotels), both offering a mix of culture and entertainment. For something more adventurous, take a thrilling ride at the Alpine Super Slide, adding excitement to your evening.

*\*Distances are measured in a straight line; actual driving distances may vary depending on the route.*

### Booking tips and Expedia advantages for Cheshire

To save money during your visit to Cheshire, plan your trip for the cheaper months of March to April or November, and aim for a Tuesday stay, as Saturdays tend to be pricier. Use Expedia’s search tool to find budget-friendly accommodations by sorting results from lowest to highest prices and applying filters for eco-friendly options. Consider booking a package that combines your hotel, flights, and activities for additional savings. Lastly, take advantage of free local attractions and consider using public transport to keep your costs down while exploring the area.

-   **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Cheshire are March to April and November, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
-   **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Cheshire is Tuesday. The most expensive day to stay in Cheshire is Saturday.
-   **Find cheap hotels on Expedia:** Expedia’s search tool enables you to set your budget, choose your desired location, and much more. You can easily arrange your search results from the lowest to highest prices, ensuring you find the most affordable hotels first. Additionally, you have the option to narrow down your choices by hotel type. For instance, selecting the Eco-certified filter will display sustainable and environmentally-friendly hotels available for booking.
-   **Consider bundling your trip:** You can save money by combining your hotel stay in Cheshire with your flights and activities through an Expedia package.

### Find the best attractions near Cheshire

Cheshire, Massachusetts, is an excellent destination for outdoor enthusiasts, offering skiing, adventure, and various cultural experiences. Key points of interest include the local library, scenic mountains, and arts centre. Visitors can explore the Cheshire Military Museum, the charming Cheshire Village, and nearby attractions like Chester, the Cheshire Ring, and Cheshire Oaks, making it a delightful spot for families and culture seekers alike.

-   **[Mount Greylock:](https://www.expedia.ca/Mount-Greylock-Hotels.0-l6091829-0.Travel-Guide-Filter-Hotels)** Experience the beauty of Massachusetts' highest peak, just 8.0km from Cheshire. This mountain offers stunning vistas and thrilling outdoor adventures, perfect for hiking and nature photography.
-   **[Mount Greylock State Reservation Visitor Center:](https://www.expedia.ca/Mount-Greylock-State-Reservation-Visitor-Center-Hotels.0-l6272782-0.Travel-Guide-Filter-Hotels)** Located 4.8km away, this visitor centre is an ideal spot for families. It provides information on the area's natural wonders and access to various outdoor activities, ensuring a fun-filled day for all ages.
-   **[Williams College:](https://www.expedia.ca/Williams-College-Hotels.0-l6091833-0.Travel-Guide-Filter-Hotels)** A historic institution situated 16.1km from Cheshire, Williams College boasts a rich cultural atmosphere. Explore its beautiful campus, art galleries, and vibrant community events that reflect the college's esteemed heritage.

### Best time to go to Cheshire

The best time to visit Cheshire is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

| **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** |
| --- | --- | --- | --- | --- | --- |
| January | 19.9°F (-6.7°C) | Light Rain | Mostly Cloudy | Average | Average |
| February | 22.1°F (-5.5°C) | Light Rain | Mostly Cloudy | Moderately Low | Average |
| March | 29.7°F (-1.3°C) | Light Rain | Mostly Cloudy | Average | Slightly Low |
| April | 41.4°F (5.2°C) | Light Rain | Mostly Cloudy | Average | Slightly Low |
| May | 53.8°F (12.1°C) | Light Rain | Mostly Sunny | Average | Average |
| June | 61.5°F (16.4°C) | Light Rain | Mostly Sunny | Moderately High | Average |
| July | 67.6°F (19.8°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High |
| August | 65.7°F (18.7°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High |
| September | 58.6°F (14.8°C) | Light Rain | Mostly Sunny | Average | Average |
| October | 47.7°F (8.7°C) | Light Rain | Mostly Cloudy | Average | Slightly High |
| November | 35.4°F (1.9°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low |
| December | 27.0°F (-2.8°C) | Light Rain | Mostly Cloudy | Moderately Low | Average |

### The nearest major airports for your trip to Cheshire

When visiting Cheshire, Massachusetts, you can fly into several major airports. Bradley International Airport ([BDL](https://www.expedia.ca/Bradley-Intl-Airport-Hotels.0-aBDL-0.Travel-Guide-Filter-Hotels)) in Hartford, CT, is 80.5km away, with nearby accommodations like the [DoubleTree by Hilton Hartford - Bradley Airport](https://www.expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.Hotel-Information), just 1.6km from the airport. Albany International Airport ([ALB](https://www.expedia.ca/Albany-Intl-Airport-Hotels.0-aALB-0.Travel-Guide-Filter-Hotels)) is closer at 56.3km and offers options such as the [Park Manor Hotel](https://www.expedia.ca/Clifton-Park-Hotels-Park-Manor-Hotel.h895584.Hotel-Information), located 12.9km away. The nearest airport is Pittsfield Municipal Airport (PSF), only 19.3km from Cheshire, where you can stay at [The Central Downtown Inn & Suites](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information), just 3.2km from the airport. Each airport provides convenient access to nearby hotels for your stay.

## Recent reviews of Cheshire hotels

![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

5/5 Excellent

"As always, lovely. "

A verified traveller stayed at The Porches Inn at Mass MoCA

Posted 21 hours ago

[](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.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

5/5 Excellent

"Great service. Attentive staff. Great location. Rooms clean and comfortable. Thanks for another great stay! "

A verified traveller stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel

Posted 1 day ago

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

5/5 Excellent

"Great property, nice staff, lovely rooms, awesome location."

A verified traveller stayed at Hotel Downstreet, an Ascend Collection Hotel

Posted 2 days ago

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

5/5 Excellent

"Everything was a great experience "

A verified traveller stayed at The Yankee, Trademark Collection by Wyndham

Posted 3 days ago

[](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

5/5 Excellent

"Great"

A verified traveller stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Posted 5 days ago

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

5/5 Excellent

"Everything was great. "

A verified traveller stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG

Posted 6 days ago

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

![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg)

### Hampton Inn & Suites Berkshires-Lenox

5/5 Excellent

"Yes"

A verified traveller stayed at Hampton Inn & Suites Berkshires-Lenox

Posted 7 days ago

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

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

### Berkshire Mountain Lodge

5/5 Excellent

"Everything was perfect!!!! Check in quick, staff so helpful. Room perfect!"

A verified traveller stayed at Berkshire Mountain Lodge

Posted 7 days ago

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

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

### Vacation Village in the Berkshires

5/5 Excellent

"Nice place to stay, off season. Price was very reasonable. Room was comfortable, (1st floor, Building 5), entire building was very quiet, hardly anyone on the property. Nice amenities, but we only walked through, did not use (pool, locker rooms, hot tub, fire pit). Room was nicely appointed and comfortable. Gas fireplace worked well, hot water was plentiful, water pressure was good. Kitchen was stocked with just about anything you'd need to cook simple meals. Great option when in the area, would recommend and would stay again."

A verified traveller stayed at Vacation Village in the Berkshires

Posted 8 days ago

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

## Frequently asked questions

### When is the best time to go to Cheshire?

> The most popular time to visit Cheshire is during the summer months, particularly July and August. At this time, the climate is pleasantly warm, with average temperatures ranging from 17 to 22°C, making it superb for exploring the stunning countryside and charming towns.
> 
>   
> 
> During the peak season of June to August, Cheshire comes alive with a variety of outdoor activities and events. Attractions such as the beautiful Tatton Park and the historic Chester Zoo are bustling with families and nature enthusiasts alike. The delightful weather lends itself to leisurely walks along the picturesque canals or through the scenic gardens, allowing you to fully immerse yourself in the region's natural beauty.
> 
>   
> 
> For couples seeking romance, these summer months offer vibrant festivals, open-air concerts, and various local events that showcase Cheshire's rich heritage. Imagine indulging in al fresco dining at one of the many quaint bistros, where you can enjoy seasonal dishes made from local produce while soaking up the lively atmosphere.
> 
>   
> 
> If you're looking for a slightly quieter experience, consider visiting in September. This month often sees fewer crowds while still enjoying lovely weather and the beautiful autumn colours beginning to emerge. You'll be able to explore the area at a more leisurely pace and perhaps take advantage of some off-peak pricing on accommodations and activities.

### Can I cancel my hotel reservation on Expedia?

> Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Cheshire hotel for you.

### How can I save on a Cheshire hotel booking with Expedia?

> Before booking your Cheshire hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia.

### How much is the nightly rate at a Cheshire hotel?

> Prices for hotels in Cheshire often vary, but you can find a great deal from CA $98 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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-   [Dalton Vacation Rentals](https://www.expedia.ca/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals)

-   [Book Hotels in Cheshire on Expedia.com](https://www.expedia.com/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)

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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)