A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Cheshire bed & breakfast

Exterior

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ￥38,601
￥40,802 total
includes taxes & fees
Aug 12 - Aug 13
Harbour House Inn
Terrace/patio

2. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (152 reviews)
"Incredible staff, free parking and cute rooms!"
Canada
Priscilla
The price is ￥34,687
￥38,746 total
includes taxes & fees
Aug 10 - Aug 11
The Trail in Adams - Berkshires’ Art Hotel
Front of property

3. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (383 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is ￥42,569
￥47,550 total
includes taxes & fees
Sep 3 - Sep 4
Chambery Inn
Front of property - evening/night

4. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is ￥62,910
￥70,270 total
includes taxes & fees
Sep 1 - Sep 2
Devonfield Inn B&B
Front of property

5. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (101 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area."
United Kingdom
Michele
The price is ￥64,140
￥75,227 total
includes taxes & fees
Aug 13 - Aug 14
The Inn at Stockbridge
Exterior

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is ￥28,042
￥32,264 total
includes taxes & fees
Aug 25 - Aug 26
The Cornell Inn, Lenox & The Berkshires
Property grounds

7. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (509 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is ￥26,536
￥29,641 total
includes taxes & fees
Aug 17 - Aug 18
Whistler's Inn Bed & Breakfast
1 bedroom, WiFi, bed sheets

8. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is ￥49,120
￥64,269 total
includes taxes & fees
Aug 25 - Aug 26
Experience Timeless Elegance in The Edith Wharton Room!
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

9. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (75 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion for improvement is breakfast - last year it was much better."
United States
Tatyana
The price is ￥111,501
￥124,547 total
includes taxes & fees
Aug 31 - Sep 1
33 Main
3 bedrooms, bed sheets

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is ￥49,120
￥64,269 total
includes taxes & fees
Aug 25 - Aug 26
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

11. Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is ￥54,168
￥69,354 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is ￥56,692
￥74,187 total
includes taxes & fees
Aug 20 - Aug 21
Historic Susan B. Anthony Room - Cozy & Charming Stay
Interior

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is ￥63,001
￥82,305 total
includes taxes & fees
Aug 16 - Aug 17
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, bed sheets

14. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is ￥73,097
￥93,277 total
includes taxes & fees
Aug 26 - Aug 27
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

15. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is ￥68,049
￥88,271 total
includes taxes & fees
Aug 31 - Sep 1
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Front of property

16. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (171 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is ￥41,904
￥48,069 total
includes taxes & fees
Aug 16 - Aug 17
Brook Farm Inn
Fireplace

17. Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
The price is ￥80,668
￥105,387 total
includes taxes & fees
Aug 25 - Aug 26
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area

18. Elegant suite with a king bed, fireplace, and kitchenette.

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is ￥80,668
￥105,387 total
includes taxes & fees
Aug 25 - Aug 26
Elegant suite with a king bed, fireplace, and kitchenette.
Suite, Private Bathroom (RedBird Suite) | View from room

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (114 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is ￥52,058
￥62,974 total
includes taxes & fees
Aug 26 - Aug 27
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Garden

20. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (465 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ￥34,017
￥37,316 total
includes taxes & fees
Aug 10 - Aug 11
Shaker Mill Inn
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"This was our fourth year in a row staying at the Inn. They have a new sitting area outside with a gas fire pit, very nice. The pool is always very well maintained. We like to stay in the older section room away from the main building, the beds are comfortable and the room is basic but clean and nice. The breakfast is as good as any other hotel brand that offers breakfast. The shopping center is right next door within walking distance, with a few places to eat. It’s a great location also to get to anywhere in the area."
Zachary 2-night trip
Posted 6 hours ago
The Yankee Inn

Find out more about Cheshire

Cheshire B&B information

Number of reviews
1,742
Accommodation
46 B&B
Lowest Price
￥29,641
Highest Price
￥124,547

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 attractions in town, Mount Greylock State Reservation and Cheshire Reservoir are worth a stop.
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: 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: 14.8 mi (23.9 km) from the downtown core. Enjoy the free full breakfast and unique décor. Chambery Inn: 9 rooms. 18.1 mi (29.1 km) from the heart of downtown. Enjoy the private yard and deli. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. Located 4.7 mi (7.5 km) from the core of Cheshire. Enjoy the unique décor and patio area.
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 spend some time in the great outdoors, Mount Greylock State Reservation and Cheshire Reservoir are some notable spots. You might also consider a trip to sites like Mount Greylock State Reservation Visitor Center or Susan B. Anthony Birthplace Museum 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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