Title: Book The Best Hotels in Cheshire, MA for 2025 from CA $105 - Competitive Prices - Expedia.ca

  

[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)

![The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..](https://images.trvl-media.com/place/6005398/5524f182-4aec-4e46-bab1-4eb1dd804bd0.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Ed Gaffny

# Find hotels in Cheshire, MA from CA $105

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## Go beyond your typical stay in Cheshire

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=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&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=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&travelerType=family_friendly)

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=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&lodging=CABIN)

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=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&amenities=HOT_TUB)

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=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&lodging=AGRITOURISM)

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=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&amenities=PETS)

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=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&lodging=APARTMENT)

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=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&lodging=COTTAGE)

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=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&lodging=CONDO)

## Check prices for these dates

Tonight

[Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 1,003 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)

![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)

![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.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)

### Harbour House Inn

Cheshire

9.4/10

Exceptional

(52)

"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 $341

CA $361 total

includes taxes & fees

Nov 4 - Nov 5

[](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)

![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)

![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)

![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)

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

Lee

9.0/10

Wonderful

(1002)

"We had a lakeside room which was wonderful!"

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

Nancy

CA $153

CA $171 total

includes taxes & fees

Nov 9 - Nov 10

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

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

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Untold

Lenox

9.0/10

Wonderful

(787)

"Easy parking, great community spaces, beautiful decor! "

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

Kerry

CA $130

CA $145 total

includes taxes & fees

Nov 2 - Nov 3

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

![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.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)

![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)

### The Yankee, Trademark Collection by Wyndham

Lenox

9.0/10

Wonderful

(1025)

"Great place. Friendly staff and very well located. Great breakfast options. "

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

Abiezer

CA $150

CA $167 total

includes taxes & fees

Nov 2 - Nov 3

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

![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)

![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Pittsfield

8.0/10

Very good

(935)

"Enjoyable stay. Staff were very nice. "

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

Claire

CA $144

CA $161 total

includes taxes & fees

Dec 2 - Dec 3

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

![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)

![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Village in the Berkshires

Williamstown

8.8/10

Excellent

(2116)

"Good location; reasonable price; very clean and quiet - would definitely return"

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

Steven

CA $127

CA $157 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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/a866db4a.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)

![Indoor pool, open 6:00 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/ecbe7d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Downstreet, an Ascend Collection Hotel

North Adams

8.8/10

Excellent

(1004)

"Staff was very welcoming and friendly! They provided great tips on restaurants and things to do in are."

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

Robert

CA $209

CA $233 total

includes taxes & fees

Nov 9 - Nov 10

[](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)

![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)

![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/74865ec0.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)

### Berkshire Mountain Lodge

Pittsfield

9.0/10

Wonderful

(741)

"Great stay, perfect "

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

Lawrence

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

![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a5a66acc.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)

![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)

### The Cornell Inn, Lenox & The Berkshires

Lenox

9.0/10

Wonderful

(1002)

"Honestly I just enjoyed being able to relax Play some games in the cute pub and the breakfast was yummy and stuff was inviting and so helpful "

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

Sandra

CA $180

CA $256 total

includes taxes & fees

Nov 2 - Nov 3

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

![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)

![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.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

(773)

"Lovely spot, great accommodations, friendly staff, and great location."

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

Joanne

CA $164

CA $203 total

includes taxes & fees

Nov 19 - Nov 20

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

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/a89bc327.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)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/2b026b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Pittsfield

9.4/10

Exceptional

(55)

"Bright new hotel with very friendly and helpful staff. "

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

Mary

CA $166

CA $185 total

includes taxes & fees

Dec 2 - Dec 3

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

![Suite (Main Inn Queen)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3ac2703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.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)

### The Red Lion Inn

Stockbridge

8.8/10

Excellent

(1025)

"Food was great!"

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

Emily

CA $202

CA $289 total

includes taxes & fees

Nov 6 - Nov 7

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

![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)

![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.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)

### The Williams Inn

Williamstown

9.6/10

Exceptional

(532)

"Great stay"

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

SIDNEY

CA $276

CA $308 total

includes taxes & fees

Nov 17 - Nov 18

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

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/bd64a090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/3ed5d9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c204d876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FairBridge Inn Express

Pittsfield

5.4/10

(803)

"Good service and people"

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

Jerod

CA $94

CA $105 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.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)

![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.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)

![Interior entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c3ea2282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel On North

Pittsfield

9.6/10

Exceptional

(788)

"Clean modern place in town, good value. Room on street side was a little noisy at night, ask for back room if light sleeper. Restaurant was not good value. "

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

Michael

CA $187

CA $209 total

includes taxes & fees

Nov 17 - Nov 18

[](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)

![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)

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

### The Porches Inn at Mass MoCA

North Adams

9.4/10

Exceptional

(432)

"Excellent place! "

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

Francisco

CA $225

CA $282 total

includes taxes & fees

Dec 2 - Dec 3

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

![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/663f69c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/w2880h1917x0y0-550a94f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/7b669948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed with Sofa bed (Dewey Carriage House Inn)](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/468cf971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Constance by the Lenox Collection

Lenox

8.4/10

Very good

(558)

"I liked the old world decor and the living room area to chill out in "

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

Jelena

CA $152

CA $170 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Lenox-Hotels-Rookwood-Inn.h4945461.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/3e40d6cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/7720f0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/0c3db9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/8e0c73d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Williamstown Motel

Williamstown

9.4/10

Exceptional

(309)

"It was clean and in a convenient location "

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

Karen

CA $128

CA $144 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/c81c0732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/d28e6aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe King Interior Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/88509527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Central Downtown Inn & Suites

Pittsfield

8.8/10

Excellent

(334)

"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"

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

Candee

CA $158

CA $177 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.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)

![Reception](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/be737544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Williamstown

Williamstown

8.8/10

Excellent

(390)

"We really liked the beautiful fire pit and the warm cup of tea after coming home from dinner."

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

Kathleen

CA $220

CA $245 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.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=2025-11-15&endDate=2025-11-16&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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## Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting.

[See all hotels in Cheshire](https://www.expedia.ca/Hotel-Search?startDate=2025-11-15&endDate=2025-11-16&adults=2&regionId=6005398)

![The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..](https://images.trvl-media.com/place/6005398/5524f182-4aec-4e46-bab1-4eb1dd804bd0.jpg?impolicy=fcrop&w=899&h=675&p=1&q=high)

Photo by Ed Gaffny

### 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

![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, Routes 7 and 20, Lenox, MA

CA $110

CA $123 total

Nov 9 - Nov 10

includes taxes & fees

7.4/10 Good! (815 reviews)

[](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.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 $150

CA $167 total

Nov 2 - Nov 3

includes taxes & fees

9/10 Wonderful! (1,020 reviews)

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

Nov 4 - Nov 5

includes taxes & fees

8.4/10 Very Good! (1,022 reviews)

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

![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

Nov 16 - Nov 17

includes taxes & fees

8.2/10 Very Good! (1,004 reviews)

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

![FairBridge Inn Express](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### FairBridge Inn Express

16 Cheshire Road, Pittsfield, MA

CA $94

CA $105 total

Nov 4 - Nov 5

includes taxes & fees

5.2/10 (799 reviews)

[](https://expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.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 $156

CA $174 total

Nov 9 - Nov 10

includes taxes & fees

9/10 Wonderful! (1,004 reviews)

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

## Hotels in Cheshire with star-rating

![4 Star Hotels](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_w.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/2000000/1070000/1066500/1066423/012d1fc0_w.jpg)

3 Star Hotels

99 properties

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

![2 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_w.jpg)

2 Star Hotels

89 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

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

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

5/5 Excellent

"The restaurant was so delicious …the fries were the best fries I have ever had …will never forget how tasty they were !!!"

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

Posted 1 day ago

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

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

### The Red Lion Inn

5/5 Excellent

"The Red Lion Hotel was a great place to stay!! I would definitley come back again and stay there! I loved the bar downstairs and the restaurant! Our room was perfect and we had lots of room! The bed was super comfy - a marshmallow bed!! LOL! The location was nice to walk to the different shops in town! Fun place! "

A verified traveller stayed at The Red Lion Inn

Posted 2 days ago

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

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

### Berkshires Untold

5/5 Excellent

"This property was great for our weekend getaway. It is conveniently located "

A verified traveller stayed at Berkshires Untold

Posted 3 days ago

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

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

### Berkshire Mountain Lodge

5/5 Excellent

"Excellent all the way around"

A verified traveller from Cantonment stayed at Berkshire Mountain Lodge

Posted 4 days ago

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

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

### Vacation Village in the Berkshires

5/5 Excellent

"Good location; reasonable price; very clean and quiet - would definitely return"

A verified traveller from Queensbury stayed at Vacation Village in the Berkshires

Posted 4 days ago

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

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//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

"Very clean and roomy lodge (2 bedrooms); conveniently located; has kitchen; recreational facilities a bit dated. Will come back again. "

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)

![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg)

### Best Western Plus Berkshire Hills Inn & Suites

5/5 Excellent

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

A verified traveller stayed at Best Western Plus Berkshire Hills Inn & Suites

Posted 5 days ago

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

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg)

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

5/5 Excellent

Awesome Stay

"View of the lake was lovely! Breakfast was fine—yogurt, eggs, pancakes and cereal. Coffee was plentiful!"

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

Posted 5 days ago

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

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

### The Williams Inn

5/5 Excellent

"Lovely property, friendly, helpful staff. Modern, large rooms. Pretty decor."

A verified traveller stayed at The Williams Inn

Posted 6 days ago

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

## Frequently asked questions

### How much does a hotel in Cheshire with high-speed wifi cost?

> Enjoy staying in a hotel in Cheshire with high-speed wifi, with plenty of hotels from CA $105 offering top amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during the weekend or around public holidays. Prices can vary depending on the location, season, and hotel amenities.

### Do any hotels in Cheshire provide wifi access by the pool or in common areas?

> The [Harbour House Inn](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) is a charming 3.5-star hotel located in Cheshire, Massachusetts, great for travellers seeking comfort and convenience. With a remarkable review rating of 9.6, guests often rave about its inviting atmosphere and thoughtful amenities.
> 
>   
> 
> One of the standout features of the Harbour House Inn is its free WiFi access, available in common areas, allowing you to stay connected while enjoying the stunning mountain views. Whether you're lounging by the pool or relaxing in the communal spaces, you can easily catch up on emails or share your holiday snaps with friends and family.
> 
>   
> 
> Additionally, guests appreciate the complimentary breakfast, which adds to the overall value and convenience of their stay.

### What are the best hotels with wifi near Mount Greylock State Reservation?

> The [Harbour House Inn](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) is a delightful 3.5-star establishment great for those seeking a comfortable stay near Mount Greylock State Reservation. Guests rave about its breathtaking mountain views, which create a serene backdrop for your adventures.
> 
>   
> 
> Start your day right with a complimentary full breakfast, setting you up for exploration in the stunning natural surroundings. With free WiFi available throughout the property, staying connected is a breeze, whether you're sharing your experiences with friends or planning your next excursion.
> 
>   
> 
> With a remarkable traveller rating of 9.6, the Harbour House Inn prides itself on offering top hotels and amenities that cater to both families and those seeking a peaceful getaway.

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

> With Expedia, you'll unlock our lowest prices by joining [One Key™](https://www.expedia.ca/welcome-one-key), our travel rewards program. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on hotels with WiFi in Cheshire. Typically, booking in advance will help you save on your hotel stay. If you're feeling spontaneous, be sure to check for [last-minute deals](https://www.expedia.ca/lp/b/vacations/last-minute-deals).

### 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. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Cheshire for you.

### What dining options are typically available in Cheshire ski accommodations?

> Cheshire ski accommodations typically offer a range of dining options to suit various preferences, from casual to more formal settings.
> 
>   
> 
> You'll often find a main restaurant on-site, serving breakfast, lunch, and dinner. These restaurants usually feature local New England cuisine, incorporating regional ingredients. Some may offer a buffet-style breakfast, while dinner could be à la carte with options like roasted meats, fresh seafood, and seasonal vegetables.
> 
>   
> 
> For those looking for a quicker bite or a more relaxed atmosphere, many accommodations include a casual cafe or a grab-and-go deli. These spots are great for a coffee and pastry in the morning, a light sandwich for lunch, or snacks throughout the day. They're particularly convenient for families who want to maximise their time on the slopes.
> 
>   
> 
> Additionally, some larger ski resorts in Cheshire might feature a pub or a lounge bar. These venues are ideal for unwinding after a day of skiing, offering a selection of local craft beers, wines, and spirits, alongside a menu of pub classics like burgers, wings, and hearty soups.

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

> Members always get our best prices. Find our best Cheshire ski hotel deals by joining Expedia's free travel rewards program—[One Key™](https://www.expedia.ca/welcome-one-key). As a member, you can unlock instant savings and member perks when you're logged in. Another tip is to book your ski hotel in advance as availability and prices are usually better. If you are feeling spontaneous, there are last-minute offers to explore too.

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

> If your plans change, it's easy to cancel your hotel with free cancellation on Expedia. Just use the "Fully refundable property" filter during your search to find the right ski hotel in Cheshire. Before confirming your booking, review the property's cancellation policy for complete peace of mind.

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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.

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