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Compare 22 B&B in East Canaan with updated reviews, rates, and availability.

Blackberry River Inn
Breakfast meal
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (85)
"Very cute inn with amazing breakfast!"
The price is AED 633
AED 711 total
includes taxes & fees
6 Nov - 7 Nov
Blackberry River Inn
Locust Tree Bed and Breakfast LLC
Exterior
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (365)
"Nice B&B that was close to an event we had at the Great Falls Brewery in Canaan. Very quiet. The bed was clean but here were some cobwebs under the bed and bedstands. The shower/tub also didn't seem to be very clean. In any case, it was affordable and perfect for a night in the CT mountains."
The price is AED 386
AED 444 total
includes taxes & fees
6 Nov - 7 Nov
Locust Tree Bed and Breakfast LLC
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (359)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
The price is AED 698
AED 779 total
includes taxes & fees
6 Nov - 7 Nov
Chambery Inn
Inn at Pine Plains
Breakfast area
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (277)
"Ideal version of a New England inn. "
The price is AED 937
AED 1,051 total
includes taxes & fees
6 Nov - 7 Nov
Inn at Pine Plains
Wilder House Berkshires
Living area
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (9)
"Beautiful property, super clean, close to great Barrington, and has EV charging, which was a plus. Can’t wait to visit again. "
The price is AED 437
AED 488 total
includes taxes & fees
7 Nov - 8 Nov
Wilder House Berkshires
Granville House
Room
Granville House
3.0 star property
10.0 out of 10, Exceptional, (76)
"The surroundings were quiet and peaceful. The hosts were welcoming and friendly. Wonderful people "
The price is AED 735
AED 821 total
includes taxes & fees
10 Nov - 11 Nov
Granville House
Manor House Inn
Restaurant
Manor House Inn
3.0 star property
9.2 out of 10, Wonderful, (134)
"The woodwork and stained glass. "
The price is AED 1,209
AED 1,336 total
includes taxes & fees
8 Nov - 9 Nov
Manor House Inn
Devonfield Inn B&B
Room
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (116)
"The Inn is very nice, however the room received was too small and was very limited for comfort. Breakfasts were great and the concert on Saturday was especially special. Would stay again if another room was available . "
The price is AED 1,025
AED 1,145 total
includes taxes & fees
12 Nov - 13 Nov
Devonfield Inn B&B
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (96)
"Well-run and elegant property. "
The Inn at Stockbridge
Tanglewood Suites
Property grounds
Tanglewood Suites
2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is AED 804
AED 804 total
includes taxes & fees
6 Nov - 7 Nov
Tanglewood Suites
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is AED 1,685
AED 2,039 total
includes taxes & fees
6 Nov - 7 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Room
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is AED 3,673
AED 4,685 total
includes taxes & fees
6 Nov - 7 Nov
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Bathroom
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
2.0 out of 10, (1)
"Never even met the inn keepers...no one is in sight...WiFi wouldn’t work...a/c in room would not stay on.....1 item only for breakfast- delivered to room- that has no table or chair- stood in the bathroom to eat!!!! Very expensive for what u get "
The price is AED 3,673
AED 4,685 total
includes taxes & fees
6 Nov - 7 Nov
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Room
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
10.0 out of 10, Exceptional, (4)
"The property was a converted parochial school The rooms were old class rooms. Very spacious and extremely comfortable. Lots to do in the area or like we did just relax . We would recommend the inn for a great summer getaway . Community theater is a big attraction although not open yet Enjoy"
The price is AED 3,673
AED 4,685 total
includes taxes & fees
6 Nov - 7 Nov
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
Interior
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
10.0 out of 10, Exceptional, (6)
The price is AED 3,673
AED 4,685 total
includes taxes & fees
6 Nov - 7 Nov
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace
Room
Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace
8.4 out of 10, Very Good, (10)
"Room was not what i reserverd I left inn and need a refund Spent an hour on the phone with Travelocity Outside inn trying to resolve reservation With no resolve I left Inn "
The price is AED 3,673
AED 4,685 total
includes taxes & fees
6 Nov - 7 Nov
Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace
The Red Door B&B
Exterior
The Red Door B&B
3.0 star property
10.0 out of 10, Exceptional, (5)
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B
Hilltop House Bed & Breakfast
Front of property - evening/night
Hilltop House Bed & Breakfast
3.0 star property
9.0 out of 10, Wonderful, (82)
"The bed is so good. "
Hilltop House Bed & Breakfast
Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
Miscellaneous
Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
Romantic Boutique Hotel / Bed and Breakfast - SchoolHouse Suite
Room
Romantic Boutique Hotel / Bed and Breakfast - SchoolHouse Suite
9.6 out of 10, Exceptional, (8)
The price is AED 3,673
AED 4,685 total
includes taxes & fees
6 Nov - 7 Nov
Romantic Boutique Hotel / Bed and Breakfast - SchoolHouse Suite
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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Other property types in East Canaan

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Lake-we provide kayaks and a canoe!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (208)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
Exterior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (195)
"My husband and I loved our stay there.. The house was very clean with a beautiful scenic back yard. Enjoyed the porch and the view of the lake. Easy check in and check out.. I would highly recommend this place."
Peace and quiet on the lake
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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.

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. Granville House: 5 rooms. Located 15.7 mi (25.3 km) from the core of East Canaan. Enjoy the free full 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 Land of Nod Vineyard and Winery and Beckley Furnace Industrial Park. Infinity Music Hall and Bistro and Music Mountain 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.