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Compare 22 B&B in 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, (91)
"The room with bathroom was very comfortable and clean. The property was extensive and well maintained. Breakfast choices were extensive and our choices were delicious and cooked by Lucas."
The price is AED 576
AED 647 total
includes taxes & fees
28 Nov - 29 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, (367)
"It was okay"
The price is AED 386
AED 444 total
includes taxes & fees
27 Nov - 28 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
1 Dec - 2 Dec
Chambery Inn
Inn at Pine Plains
Breakfast area

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (278)
"Ideal version of a New England inn. "
The price is AED 937
AED 1,051 total
includes taxes & fees
1 Dec - 2 Dec
Inn at Pine Plains
Wilder House Berkshires
Living area

Wilder House Berkshires

2.0 star property
9.8 out of 10, Exceptional, (10)
"Great place, very clean, hospitable and designed with impeccable taste. "
The price is AED 577
AED 645 total
includes taxes & fees
10 Dec - 11 Dec
Wilder House Berkshires
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (117)
"Arrived Friday to see a Tanglewood concert. Inn provided lovely afternoon cocktails and appetizers with piano music. Saturday hosts sponsored garden concert with local artists - really nice after morning hike to water fall and early afternoon golf. Yummy Morning breakfast each day. Central to Stonebridge and Lenox. Hosts very knowledgeable "
The price is AED 1,062
AED 1,186 total
includes taxes & fees
3 Dec - 4 Dec
Devonfield Inn B&B
Manor House Inn
Restaurant

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"A charming old manor from the Gilded Age, thoughtfully updated and modernized without losing the soul of the original home. Incredibly comfortable rooms, inviting common spaces, excellent breakfast, beautiful grounds, and friendly staff. We especially enjoyed the fireplace in our room. Perfect for a romantic getaway, we look forward to visiting again in the future."
Manor House Inn
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
1 Dec - 2 Dec
Granville House
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
27 Nov - 28 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
29 Nov - 30 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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
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
27 Nov - 28 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
27 Nov - 28 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
28 Nov - 29 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
27 Nov - 28 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
27 Nov - 28 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
27 Nov - 28 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 Canaan

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated
Exterior

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

9.8 out of 10, Exceptional, (9)
"We loved our stay! Andrea responded to questions very quickly. The house was very clean and had everything we needed. We appreciated the treat that was left on the island. We were there only 2 nights and wish we stayed longer. We would definitely stay again. "
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
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 Canaan?
If you want to find an accommodation with fewer rooms than a hotel and a more personalized environment, a bed and breakfast might be a great fit for your trip to Canaan. If your ideal vacation to Canaan includes spending lots of time outside, Campbell Falls State Park and Edith Scoville Memorial Sanctuary are good spots to enjoy the scenery.
How do you know if a B&B is the right choice for you?
Every B&B has its own unique feel. Whether it’s a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the small details are what make bed and breakfasts a home away from home.
What are the best bed and breakfasts in Canaan?
Here are some well-liked B&Bs in the area: Blackberry River Inn: 14 rooms. 3.8 mi (6 km) from the heart of Canaan. Enjoy the free cooked breakfast and outdoor pool. Locust Tree Bed and Breakfast LLC: 7 rooms. 0.6 mi (0.9 km) from the downtown core. Inn at Pine Plains: 8 rooms. 18 mi (28.9 km) from the heart of downtown.
When should I book my B&B in Canaan?
When you’re planning your stay in 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 Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Canaan?
When you want to spend some time in the great outdoors, Housatonic River and Campbell Falls State Park are some notable spots. You might put Edith Scoville Memorial Sanctuary and Lawrence Field on your list if you want to see more of the area.
How can I get to and around Canaan?
Mapping out your trip in and around Canaan is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 27.6 mi (44.4 km) away from the heart of the city. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 27.8 mi (44.7 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.