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Compare 16 B&B in East Canaan with updated reviews, rates, and availability.

Blackberry River Inn
Library
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (67)
"Great place to stay for enjoying NW Connecticut activities. Friendly helpful staff, comfortable room, pool, cozy public areas/lobby. The breakfast was delicious in a sunny breakfast room and the servers very gracious about special requests. Am looking forward to future stays here."
The price is ₩207,446
₩238,563 total
includes taxes & fees
Sep 30 - Oct 1
Blackberry River Inn
Locust Tree Bed and Breakfast LLC
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (350)
"A fantastic Bed and Breakfast! This bed and breakfast is located in a quiet area, close to many natural attractions both in Canaan and surrounding towns. The owners were friendly and personable. "
The price is ₩140,362
₩161,416 total
includes taxes & fees
Sep 29 - Sep 30
Locust Tree Bed and Breakfast LLC
Inn at Pine Plains
Free daily continental breakfast
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (276)
"Ideal version of a New England inn. "
The price is ₩339,066
₩380,177 total
includes taxes & fees
Sep 29 - Sep 30
Inn at Pine Plains
Wilder House Berkshires
Wilder House Berkshires Room 3 | Individually decorated, individually furnished, blackout drapes
Wilder House Berkshires
2.0 star property
10.0 out of 10, Exceptional, (5)
"The Wilder House is beautifully decorated, and our room was beautiful. There are books and games if you need to occupy your time, and Brad, the owner, is both a real sweetheart and a fine cook of the included breakfasts. Chat with him and you'll come away smiling. There are a few problems, though, most of them minor and easily remedied, such as the lack of a night light in the bathroom, the single-ply toilet tissue, and the little packets of rough facial tissue instead of a box of higher...
The price is ₩221,905
₩247,865 total
includes taxes & fees
Oct 1 - Oct 2
Wilder House Berkshires
Devonfield Inn B&B
Front of property - evening/night
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (113)
"Wonderful place for a quiet getaway for a couple of nights. Scenic setting. Delicious breakfasts, helpful owners and staff on site. We'd book again!"
The price is ₩517,242
₩577,755 total
includes taxes & fees
Sep 29 - Sep 30
Devonfield Inn B&B
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (357)
"Nice place to stay in the Berkshires. The house is very quint and the room very comfortable (especially the bed and pillows). While I did not meet Bob until I checked out, they were always available to help via text. I would go back or recommend friends to stay there."
The price is ₩398,888
₩445,558 total
includes taxes & fees
Oct 1 - Oct 2
Chambery Inn
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (95)
"Well-run and elegant property. "
The Inn at Stockbridge
Manor House Inn
Interior detail
Manor House Inn
3.0 star property
9.2 out of 10, Wonderful, (132)
"Very nice place. No complaints. Would recommend "
The price is ₩383,389
₩425,562 total
includes taxes & fees
Sep 30 - Oct 1
Manor House Inn
The Barrington
Junior Suite | Premium bedding, individually decorated, desk, iron/ironing board
The Barrington
4.0 star property
9.8 out of 10, Exceptional, (107)
"Wonderful stay. Beautifully appointed rooms, comfortable bed, hot shower, quiet and restful. Lovely touches, but the best part of all is the incredible breakfasts prepared by French chef and manager William. Having these to look forward to each morning was a joy. Highly recommend this excellent property!"
The price is ₩432,143
₩482,710 total
includes taxes & fees
Oct 4 - Oct 5
The Barrington
Granville House
Interior detail
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 ₩299,176
₩334,186 total
includes taxes & fees
Oct 21 - Oct 22
Granville House
Tanglewood Suites
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
Tanglewood Suites
2.5 star property
8.0 out of 10, Very Good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
Tanglewood Suites
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (103)
"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 ₩610,119
₩738,067 total
includes taxes & fees
Sep 30 - Oct 1
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Red Door B&B
Interior
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
Rock Hall Luxe Lodging
Outdoor pool
Rock Hall Luxe Lodging
4.5 star property
10.0 out of 10, Exceptional, (4)
"The innkeepers were extememly accomadating. They made dinner reservations for us and offered suggestions of activities. Breakfast was fantastic. Before we left, we picked apples from the onsite orchard. Highly reccomended."
Rock Hall Luxe Lodging
Federal House Inn
Room | Rollaway beds, free WiFi
Federal House Inn
3.5 star property
9.0 out of 10, Wonderful, (406)
"Beautiful old house. Personable, helpful and accommodating staff. Wonderful homemade breakfast, wine hour and snacks. We had a great stay."
Federal House Inn
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Other property types in East Canaan

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. When you want to explore some of the destination’s attractions, Land of Nod Vineyard and Winery is worth a visit.
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.
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. Average annual precipitation for East Canaan is 50 inches.
What is there to do in East Canaan?
If you want to check out some popular attractions in East Canaan, you might enjoy a visit to Land of Nod Vineyard and Winery. 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.