Search B&B in East Canaan

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for East Canaan bed & breakfast

Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AED 386
AED 443 total
includes taxes & fees
24 Dec - 25 Dec
Locust Tree Bed and Breakfast LLC
Library
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (163)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AED 604
AED 694 total
includes taxes & fees
16 Dec - 17 Dec
Blackberry River Inn
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (89)
"Outstanding all around!"
United States
Jonathan
The price is AED 731
AED 816 total
includes taxes & fees
12 Dec - 13 Dec
Granville House
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
The price is AED 565
AED 631 total
includes taxes & fees
17 Dec - 18 Dec
Wilder House Berkshires
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is AED 921
AED 1,080 total
includes taxes & fees
1 Jan - 2 January 2026
The Inn at Stockbridge
Free daily continental breakfast
Inn at Pine Plains

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (301)
"Great stay"
United Kingdom
Katherine
The price is AED 909
AED 1,028 total
includes taxes & fees
24 Dec - 25 Dec
Inn at Pine Plains
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
Tanglewood Suites

Tanglewood Suites

Tanglewood Suites
2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is AED 804
AED 804 total
includes taxes & fees
11 Dec - 12 Dec
Tanglewood Suites
Interior detail
Manor House Inn

Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (138)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is AED 1,172
AED 1,301 total
includes taxes & fees
14 Dec - 15 Dec
Manor House Inn
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Business center
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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"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
Robert
The price is AED 1,403
AED 1,697 total
includes taxes & fees
7 Jan - 8 January 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 East Canaan Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great hospitality "
regina maria 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Frequently asked questions

Searching for B&Bs in East Canaan?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a B&B might be just the right fit for your vacation to East Canaan. If your ideal vacation to East Canaan includes spending lots of time outside, Beckley Furnace Industrial Park is a good spot to enjoy the scenery.
Are you thinking about a B&B for your stay?
B&Bs all have a unique charm. Whether it's a garden for guests to admire or a beautiful breakfast room, the little details are what make bed and breakfasts a home away from home.
What are the top B&Bs in East Canaan?
Below are some B&Bs in the area: Locust Tree Bed and Breakfast LLC: 7 rooms. 1.3 mi (2.1 km) from the heart of East Canaan.Blackberry River Inn: 14 rooms. 2.2 mi (3.6 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. Wilder House Berkshires: 5 rooms. 7.7 mi (12.3 km) from the heart of downtown. Enjoy the free cooked breakfast and unique décor.
When should I stay at a B&B in East Canaan?
When you're planning your stay in East Canaan, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in East Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in East Canaan?
When you want to check out some attractions in town, you might consider a visit to Beckley Furnace Industrial Park and Land of Nod Vineyard and Winery. Haystack Mountain State Park and Infinity Music Hall and Bistro are also some sites to visit if you want to see more of the area.
How can I get to and around East Canaan?
Planning your excursions in and around East Canaan is easier with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 28.8 mi (46.3 km) from the city center. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 29.5 mi (47.6 km) away. If you'd like to explore around the area, you may want a rental car for your journey.