A lake surrounded by autumn-colored trees and hills.

Search B&B in Cheshire

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept
In one month
18 Sept - 20 Sept
In two months
16 Oct - 18 Oct

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, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is HK$1,990
HK$2,104 total
includes taxes & fees
24 Aug - 25 Aug
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, (154 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is HK$1,588
HK$1,774 total
includes taxes & fees
14 Sept - 15 Sept
The Trail in Adams - Berkshires’ Art Hotel
Exterior

3. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is HK$1,395
HK$1,605 total
includes taxes & fees
25 Aug - 26 Aug
The Cornell Inn, Lenox & The Berkshires
Garden

4. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (467 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is HK$1,475
HK$1,618 total
includes taxes & fees
8 Sept - 9 Sept
Shaker Mill Inn
Aerial view

5. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (113 reviews)
"Very nice hotel."
United States
Erdem
The price is HK$1,169
HK$1,309 total
includes taxes & fees
26 Aug - 27 Aug
Inn at Silver Maple Farm
Property grounds

6. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (514 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is HK$1,250
HK$1,396 total
includes taxes & fees
13 Sept - 14 Sept
Whistler's Inn Bed & Breakfast
Front of property

7. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (384 reviews)
"The room was clean and very quiet. Breakfast was delivered to our room as requested."
United States
Richard
The price is HK$2,118
HK$2,366 total
includes taxes & fees
17 Sept - 18 Sept
Chambery Inn
Front of property – evening/night

8. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
The price is HK$3,051
HK$3,408 total
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B
Front of property

9. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (102 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 HK$2,957
HK$3,468 total
includes taxes & fees
13 Sept - 14 Sept
The Inn at Stockbridge
1 bedroom, WiFi, bed sheets

10. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is HK$2,443
HK$3,196 total
includes taxes & fees
25 Aug - 26 Aug
Experience Timeless Elegance in The Edith Wharton Room!
Premium bedding, iron/ironing board, free WiFi, individually decorated

11. 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 HK$5,198
HK$5,807 total
includes taxes & fees
31 Aug - 1 Sept
33 Main
View from room

12. 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 HK$2,590
HK$3,133 total
includes taxes & fees
31 Aug - 1 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

13. 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 HK$2,171
HK$2,488 total
includes taxes & fees
8 Sept - 9 Sept
Brook Farm Inn
Interior

14. 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 HK$2,631
HK$3,438 total
includes taxes & fees
9 Sept - 10 Sept
Elegant Carriage House room with a queen bed and private patio.
3 bedrooms, bed sheets

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is HK$2,443
HK$3,196 total
includes taxes & fees
25 Aug - 26 Aug
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

16. 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 HK$2,694
HK$3,519 total
includes taxes & fees
31 Aug - 1 Sept
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is HK$2,819
HK$3,689 total
includes taxes & fees
31 Aug - 1 Sept
Historic Susan B. Anthony Room - Cozy & Charming Stay
1 bedroom, bed sheets

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is HK$3,635
HK$4,639 total
includes taxes & fees
26 Aug - 27 Aug
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

19. 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 HK$3,385
HK$4,426 total
includes taxes & fees
31 Aug - 1 Sept
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Fireplace

20. 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 HK$4,012
HK$5,241 total
includes taxes & fees
25 Aug - 26 Aug
Experience Luxury in The Lady Cicely Grand Suite at The Cornell 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Lovely location on Laurel lake. Our balcony was directly over looking the lake. A wonderful spot for morning coffee and a book. Dogs are welcome! Well behaved, of course. A short drive to Lenox, Tanglewood and Stockbridge. Always coming back!"
Megan 2-night trip
Posted 5 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Cheshire

Cheshire B&B information

Number of reviews
3,294
Accommodation
46 B&B
Lowest Price
HK$1,309
Highest Price
HK$5,807

Frequently asked questions

Searching for B&Bs in Cheshire?
If you want to find some accommodation with fewer rooms than the traditional hotel and an intimate environment, a B&B might be a great fit for your trip to Cheshire. When you want to explore some attractions in town, Mount Greylock State Reservation and Cheshire Reservoir are worth a stop.
Why should you consider a B&B versus a traditional hotel?
B&Bs all have a unique charm — whether it's a cosy reading space or a beautiful breakfast room, the quaint details are what make bed and breakfasts the perfect escape.
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 decor. The Cornell Inn, Lenox & The Berkshires: 14.8 mi (23.9 km) from the city centre. Enjoy the free full breakfast and unique decor. Chambery Inn: 9 rooms. Situated 18.1 mi (29.1 km) from the heart of Cheshire. Enjoy the private garden and snack bar/deli. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. 4.7 mi (7.5 km) from the city centre. Enjoy the unique decor and patio area.
When is the best time 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 temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm 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 such as 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) from the city centre. Otherwise, look 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.

Explore a world of travel with Expedia