Title: 3 Stars Hotels in Cheshire, Massachusetts from CA $138 - Find Cheap Cheshire Hotels With 3 Stars | Expedia.ca

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

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

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

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## Check availability on Cheshire 3 Star Hotels

Tonight

[Mar 6 - Mar 7](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-03-06&endDate=2026-03-07&adults=2&star=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Mar 7 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-03-07&endDate=2026-03-08&adults=2&star=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-03-06&endDate=2026-03-08&adults=2&star=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-03-13&endDate=2026-03-15&adults=2&star=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Cheshire 3-star hotels

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

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

![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.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

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

Williamstown

8.8/10

Excellent

(2,281 reviews)

"Excellent location and terrific space and amenities."

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

Michelle

CA $132

CA $162 total

includes taxes & fees

Mar 8 - Mar 9

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

![Lobby](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/201806cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/465e60d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/77fe0507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Mountain Lodge

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

Pittsfield

9.0/10

Wonderful

(869 reviews)

"Very comfortable and very close to ski slope and restaurants"

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

Frederick

CA $145

CA $193 total

includes taxes & fees

Apr 1 - Apr 2

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

![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/e88abd9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.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)

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

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

Pittsfield

8.0/10

Very good

(1,003 reviews)

"Staff was very courteous and rooms clean."

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

Steven

CA $173

CA $193 total

includes taxes & fees

Mar 7 - Mar 8

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

![Coffee service](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/7b2fadb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/185ae7e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/b4cbc760.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/1000000/10000/3000/2943/3ebde3df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Downstreet, an Ascend Collection Hotel

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

North Adams

8.8/10

Excellent

(1,005 reviews)

"Spotless and front desk staff...friendly and accommodating "

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

Barbara

CA $162

CA $180 total

includes taxes & fees

Mar 31 - Apr 1

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

![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/ed360a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.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

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

South Lee

9.0/10

Wonderful

(848 reviews)

"Great overnights stay, wish I was here longer "

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

Thomas

CA $160

CA $206 total

includes taxes & fees

Mar 8 - Mar 9

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

![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.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)

![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/6a569eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Untold

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

Lenox

9.0/10

Wonderful

(867 reviews)

"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "

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

Melissa

CA $133

CA $148 total

includes taxes & fees

Apr 1 - Apr 2

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

![Property entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Library Suite, 1 King Bed](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c5c7040f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/e65bd9d7.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)

### Hotel On North

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

Pittsfield

9.6/10

Exceptional

(826 reviews)

"Great staff, beautiful hotel. Would definitely recommend "

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

Shawn

CA $204

CA $228 total

includes taxes & fees

Mar 8 - Mar 9

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

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3e2d816d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/fa13e671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/94cb14a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Red Lion Inn

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

Stockbridge

8.8/10

Excellent

(1,000 reviews)

"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."

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

Gary

CA $222

CA $310 total

includes taxes & fees

Mar 12 - Mar 13

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

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Lee

9.2/10

Wonderful

(1,001 reviews)

"Clean room, nice staff , decent breakfast. Overall a good stay . "

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

Anindita

CA $123

CA $138 total

includes taxes & fees

Mar 29 - Mar 30

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

![Property amenity](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/27ce1034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/a63e9470.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)

![View from property](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/5e996a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Lenox Berkshires

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

Lenox

9.2/10

Wonderful

(603 reviews)

"Our stay was great! "

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

Gianna

CA $193

CA $215 total

includes taxes & fees

Mar 11 - Mar 12

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

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/66dde072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/9b4aa931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/a1e89c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/59498ff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Porches Inn at Mass MoCA

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

North Adams

9.4/10

Exceptional

(459 reviews)

"Location, hospitality, breakfast"

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

Terry

CA $208

CA $263 total

includes taxes & fees

Mar 8 - Mar 9

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

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/27ba18f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/w696h390x1y0-dec65b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/bba60f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/1715f4d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Lenox Pittsfield

[](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information)

Pittsfield

9.2/10

Wonderful

(670 reviews)

" Nice staff - beautiful hotel!"

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

MARY

CA $182

CA $203 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information)

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

![View from property](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/4e6dafd3.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/36000000/35100000/35099400/35099355/19354f8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Williamstown

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

Williamstown

8.8/10

Excellent

(405 reviews)

"Stayed one night...great breakfast"

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

Kimberley

CA $179

CA $200 total

includes taxes & fees

Apr 6 - Apr 7

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/8801cfa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/w6034h4018x7y7-c9e24ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/4c6ff871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cornell Inn, Lenox & The Berkshires

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

Lenox

9.0/10

Wonderful

(1,002 reviews)

"The Inn was very nice and the staff was super friendly and attentive."

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

Steven

CA $182

CA $210 total

includes taxes & fees

Apr 6 - Apr 7

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

![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/3908437c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Element Lenox Berkshires

[](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information)

Lenox

9.8/10

Exceptional

(22 reviews)

"Spotless rooms and the friendliest service at the front desk! "

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

Mary

CA $190

CA $212 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/ebd04e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/fae5bff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 1 Bedroom | View from room](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/2a87d01c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Ponds at Foxhollow

[](https://www.expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information)

Lenox

8.6/10

Excellent

(141 reviews)

"Great place"

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

Lisa

[](https://www.expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information)

![Dining room](https://images.trvl-media.com/lodging/111000000/110080000/110070300/110070215/595e173f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/111000000/110080000/110070300/110070215/14f6a8c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/111000000/110080000/110070300/110070215/36309153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110080000/110070300/110070215/920e0060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gregory House Country Inn

[](https://www.expedia.ca/Averill-Park-Hotels-Gregory-House-Country-Inn.h110070215.Hotel-Information)

Averill Park

9.0/10

Wonderful

(91 reviews)

"Loved the fact that we could have dinner and Sunday brunch right there."

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

Maureen

CA $150

CA $167 total

includes taxes & fees

Mar 14 - Mar 15

[](https://www.expedia.ca/Averill-Park-Hotels-Gregory-House-Country-Inn.h110070215.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/b02dfcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/fdc80b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/7d4b7b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/0bc486c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blooming Inn

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information)

Shelburne Falls

9.2/10

Wonderful

(131 reviews)

"Beautiful comfortable home with many thoughtful touches"

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

Rachel

CA $128

CA $210 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information)

![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/b35035ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/71df138f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

Hancock

8.2/10

Very good

(989 reviews)

"nice and clean, good customer service, but the room is smell. "

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

Huang

CA $203

CA $227 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/69e879d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/bd7aa934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pilates](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/c06c6b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/47826e47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gateways Inn & Restaurant

[](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information)

Lenox

8.0/10

Very good

(197 reviews)

"Gateways Inn is a fantastic place to stay! The staff was very courteous and the room was spacious and very clean. The breakfast was included and very tasty. I highly suggest a stay there if you are planning on visiting the Berkshires!!!"

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

Miguel

CA $244

CA $285 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information)

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## Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 3-star hotels. See all 4-star hotels in Cheshire.

![The Central Downtown Inn & Suites](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/4092a889_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

CA $149

CA $166 total

Mar 29 - Mar 30

includes taxes & fees

8.6/10 Excellent! (358 reviews)

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

![Lakehouse Inn](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Lakehouse Inn

615 Laurel St. Lee MA

CA $185

CA $218 total

Mar 7 - Mar 8

includes taxes & fees

9.6/10 Exceptional! (294 reviews)

[](https://expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information)

![The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183 Stockbridge MA

CA $422

CA $511 total

Mar 29 - Mar 30

includes taxes & fees

9.2/10 Wonderful! (110 reviews)

[](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information)

Still don't see what you're looking for?

[See all properties in Cheshire.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F03%2F2026&endDate=08%2F03%2F2026&regionId=6005398&star=30)

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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.

## Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and lake views. 

[See all hotels in Cheshire](https://www.expedia.ca/Hotel-Search?startDate=2026-03-20&endDate=2026-03-21&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)

## Top Cheshire Hotel Reviews

![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/27ce1034_y.jpg)

### Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Very comfortable "

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

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

### Berkshire Mountain Lodge

6/10 Okay

"The staff at the front desk was welcoming, the room was very nice. We enjoyed our stay. HOWEVER - on the day we were to arrive there was a major blizzard. There was no safe way to drive from the Boston area to Pittsfield. I called the hotel 2 days before to say that we would be arriving a day after our reservation. We had purchased cancellation insurance. When we arrived a day late I asked the front desk about a refund. They told me to call Expedia, which I did. Expedia tried to reach the hotel and was unable to do so. They referred me back to the the manager. It is now a week later and after several calls to the hotel, the manager never returned my call. I find this unacceptable."

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

![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/9903b094_y.jpg)

### Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options."

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

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

### Vacation Village in the Berkshires

10/10 Excellent

"Loved the pool and the spacious room. We'll definitely return."

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

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

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

6/10 Okay

"Fair. Pool was closed. Everything under construction. Poor location."

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

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

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

10/10 Excellent

"Room was spotless, staff was very kind!"

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

![The Ponds at Foxhollow](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd_y.jpg)

### The Ponds at Foxhollow

4/10 Poor

"I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. Front desk staff not very friendly or useful, odd because they don’t have a lot of foot traffic this time of the season. There are other similar facilities in the area that might be worth exploring versus this tired old place."

[](https://expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information)

## Find out more about Cheshire

The top 3 Stars hotels in Cheshire, Cheshire may offer some of the best discounts and rates, but these properties are anything but average. Travelers love Cheshire 3 Stars hotels for their top quality services, just-like-home amenities, and wallet-friendly prices. You can even get access to fantastic perks like delectable restaurants, so-cool cocktail bars, and spacious fitness centres.

Use the travel tools at Expedia.ca to find a cheap deal on a 3 Stars upscale hotel in Cheshire for a first-class experience, or book an inexpensive rate on one of the cheap 3 Stars hotels in Cheshire neighbourhoods near the city’s best attractions. We’ll even help you find vacation packages to go with your three star hotel in Cheshire. From last-minute work trips to long-awaited family getaways, we offer all the essentials you need to enjoy your jaunt through Cheshire.

## Frequently asked questions

### What are the best 3-star hotels in Cheshire?

### How much does it cost to stay in a 3-star hotel in Cheshire?

> - Search for the lowest price per night right now from CA $166

### What is the difference between a 4-star and 3-star hotel in Cheshire?

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