A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30
In one month
Sep 11 - Sep 13
In two months
Oct 9 - Oct 11

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 ₩359,518
₩380,009 total
includes taxes & fees
Sep 10 - Sep 11
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 ₩301,856
₩337,173 total
includes taxes & fees
Sep 14 - Sep 15
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, (1,002 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is ₩252,038
₩289,972 total
includes taxes & fees
Aug 25 - Aug 26
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, (466 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ₩264,213
₩289,841 total
includes taxes & fees
Sep 14 - Sep 15
Shaker Mill Inn
Property grounds

5. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (513 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is ₩225,744
₩252,159 total
includes taxes & fees
Sep 7 - Sep 8
Whistler's Inn Bed & Breakfast
Aerial view

6. 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 ₩225,860
₩252,963 total
includes taxes & fees
Sep 1 - Sep 2
Inn at Silver Maple Farm
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 ₩383,521
₩428,395 total
includes taxes & fees
Sep 13 - Sep 14
Chambery Inn
Front of property

8. 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 ₩535,500
₩628,074 total
includes taxes & fees
Sep 13 - Sep 14
The Inn at Stockbridge
Front of property - evening/night

9. 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 ₩552,575
₩617,222 total
includes taxes & fees
Sep 3 - Sep 4
Devonfield Inn B&B
Suite, Private Bathroom (RedBird Suite) | View from room

10. 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 ₩513,113
₩620,721 total
includes taxes & fees
Aug 30 - Aug 31
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), 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 ₩941,351
₩1,051,489 total
includes taxes & fees
Aug 31 - Sep 1
33 Main
Front of property

12. 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 ₩377,356
₩432,869 total
includes taxes & fees
Aug 16 - Aug 17
Brook Farm 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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Location great for Jacob’s pillow weekend. Small restaurant with limited menu, but had all we needed and prepared just right. Outdoor seating a plus"
Joyce 2-night trip
Posted 1 hour ago
Berkshires Untold

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,823
Accommodation
23 B&B
Lowest Price
₩252,159
Highest Price
₩1,051,489

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. Situated 18.1 mi (29.1 km) from the heart of Cheshire. Enjoy the private yard and deli. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. 4.7 mi (7.5 km) from the heart of downtown. 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 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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