Title: Cheshire B&B: Find the Best Bed and Breakfast from CA $154 | Expedia.ca

 

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Photo by Ed Gaffny

# Find a Bed and Breakfast in Cheshire from CA $154

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## Check prices for these dates

Next weekend

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

In one month

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Cheshire B&B

![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.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)

![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

(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)

![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Suite, Private Bathroom (Catamount - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/13717808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite, Private Bathroom (Rockwell - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/4d5a91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment, Private Bathroom (Greylock - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/9aba043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shaker Mill Inn

West Stockbridge

9.6/10

Exceptional

(432)

"Very casual and easy check in and out; lovely and substantial breakfast"

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

Jamie

CA $140

CA $154 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/7b825179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/38e7a71c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Shared Dormitory](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/f69b88ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/3033684f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### UU Rowe Camp and Conference Center

Rowe

CA $208

CA $220 total

includes taxes & fees

Nov 8 - Nov 9

[](https://www.expedia.ca/Rowe-Hotels-UU-Rowe-Camp-And-Conference-Center.h110897047.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/c9940794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/ca0080b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/0fed38f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pines Duplex Suite | View from room](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/7bcf94fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn at Silver Maple Farm

East Chatham

9.8/10

Exceptional

(97)

"This was the perfect spot for a Tanglewood night..beautiful, charming, great staff and delicious breakfast..."

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

Jane

CA $181

CA $202 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/5bcca6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/2bb92acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/7a497aeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/be3999ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Trail in Adams - Berkshires’ Art Hotel

Adams

9.0/10

Wonderful

(139)

"It was clean and quiet good Breakfast "

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

William

CA $243

CA $272 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.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)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/a6853cfe.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

(371)

"Lovely, unique property with huge rooms! Such a fun place to stay. "

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

Mary

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

![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/21cb26fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakehouse Inn

Lee

9.6/10

Exceptional

(287)

"Great Views & Hospitality"

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

Gerald

CA $233

CA $274 total

includes taxes & fees

Nov 7 - Nov 8

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

![Sundeck](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a02c1cad.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)

![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

(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)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6cbad311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/2d151170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Devonfield Inn B&B

Lee

10/10

Exceptional

(133)

"The inn has an excellent location and amenities."

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

Christopher

[](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/edd6aeec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/3eac4fd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/44792ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gilded Stage in the Mainhouse](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/76b1fb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Stockbridge

Lee

9.8/10

Exceptional

(98)

"A first class little inn"

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

Philip

CA $452

CA $530 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/17dab433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/3ff5efd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/bc78d43e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/e961014f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whistler's Inn Bed & Breakfast

Lenox

7.8/10

Good

(500)

"Cozy spot with very friendly propeietor"

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

Kyle

CA $319

CA $356 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Lenox-Hotels-Whistlers-Inn-Bed-Breakfast.h1197581.Hotel-Information)

![Luxury Room, 1 King Bed, Bathtub](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/2028495b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 33 Main

Lenox

10/10

Exceptional

(74)

"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."

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

James

CA $651

CA $728 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information)

![3 bedrooms, bed sheets](https://images.trvl-media.com/lodging/116000000/115170000/115170000/115169907/84b174a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, bed sheets](https://images.trvl-media.com/lodging/116000000/115170000/115170000/115169907/e10f13a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/116000000/115170000/115170000/115169907/68cd085f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/116000000/115170000/115170000/115169907/9bacc168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Lenox

CA $292

CA $428 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Lenox-Hotels-Historic-Cornell-Inn-Cozy-Berkshires-Retreat-Lenox.h115169907.Hotel-Information)

![Business centre](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Private Bathroom (RedBird Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ab46e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/5312662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Stockbridge

9.2/10

Wonderful

(109)

"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "

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

Robert

CA $434

CA $525 total

includes taxes & fees

Nov 16 - Nov 17

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/4609a9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/2f1ef067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/9a87bae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/1e673737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Elegant Carriage House room with a queen bed and private patio.

Lenox

CA $315

CA $457 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Lenox-Hotels-Elegant-Carriage-House-Room-With-A-Queen-Bed-And-Private-Patio.h115241207.Hotel-Information)

![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/23b3990f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/0e806d18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/976df379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/52586681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Experience Timeless Elegance in The Edith Wharton Room!

Lenox

CA $292

CA $428 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Lenox-Hotels-Experience-Timeless-Elegance-In-The-Edith-Wharton-Room.h115241164.Hotel-Information)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/cab9849e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/12a0d554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/67e04fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/0ab2702a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Carriage House room with a double bed and private balcony

Lenox

CA $338

CA $487 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lenox-Hotels-Cozy-Carriage-House-Room-With-A-Double-Bed-And-Private-Balcony.h115241220.Hotel-Information)

![Loft, Private Bathroom (Skylight Loft)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/48ea2807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, Private Bathroom (Victorian Room)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/49947e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Private Bathroom (Tanglewood Suite)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/c348a91f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/eb4406db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brook Farm Inn

Lenox

9.4/10

Exceptional

(162)

"This is our second stay at the Brook Farm Inn and we enjoyed it just as much as our first stay! Maureen and Joe are fantastic inn keepers. They are polite, full of knowledge and provide a wonderful experience. Our room was cozy and comfortable. The breakfast was delicious. We couldn’t ask for a better weekend away! "

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

John

[](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/5094c384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/b9beadbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/4d1c49db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/e222ef75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox

CA $359

CA $514 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Lenox-Hotels-Historic-Susan-B-Anthony-Room-Cozy-Charming-Stay.h115241178.Hotel-Information)

![Fireplace](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/af794997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/31755c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/828c0eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/64c22087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Lenox

CA $460

CA $642 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lenox-Hotels-Experience-Timeless-Elegance-In-The-Niles-Johnson-Room-At-The-Cornell-Inn.h115241126.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.

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## Top Cheshire Hotel Reviews

![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

10/10 Excellent

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

[](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

10/10 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! "

[](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

10/10 Excellent

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

[](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

10/10 Excellent

"Excellent all the way around"

[](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

10/10 Excellent

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

[](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

10/10 Excellent

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

[](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

10/10 Excellent

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

[](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

10/10 Excellent

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

[](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

10/10 Excellent

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

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

## Find out more about Cheshire

## Cheshire B&B information

| Number of reviews | 2,754 |
| --- | --- |
| Accommodation | 35 B&B |
| Lowest Price | CA $154 |
| Highest Price | CA $728 |

## Frequently asked questions

### Searching for B&Bs in Cheshire?

> If you want to find a place to stay with a small number of rooms and a more personalized environment, a B&B might be a great fit for your vacation to Cheshire. When you want to explore some of the destination's attractions, Mount Greylock State Reservation is worth a visit.

### Why would you choose a B&B versus a traditional hotel?

> B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a fun place to get away.

### What are the best B&Bs in Cheshire?

> Below are some well-liked B&Bs in the area: [Harbour House Inn](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information): 6 rooms. 1.2 mi (2 km) from the heart of Cheshire. Enjoy the free full breakfast and unique décor. [The Cornell Inn, Lenox & The Berkshires](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information): 14.8 mi (23.9 km) from the downtown core. Enjoy the free full breakfast and unique décor. [Lakehouse Inn](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information): 14 rooms. 17.1 mi (27.5 km) from the heart of downtown. Enjoy the free full breakfast and deli. [Chambery Inn](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information): 9 rooms. Located 18.1 mi (29.1 km) from the core of Cheshire. Enjoy the private yard and deli.

### What's the best time of year to book my B&B in Cheshire?

> When you're planning your stay in Cheshire, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

### What is there to do in Cheshire?

> When you want to explore some things to do in Cheshire, consider a visit to Mount Greylock State Reservation. You might also consider a trip to sites like Mount Greylock State Reservation Visitor Center or Mount Greylock if you have time to see more of the area.

### How can I get to and around Cheshire?

> Mapping out your trip in and around Cheshire is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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