Photo by Robin/Loving Life

Search B&B in Canaan

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 28 B&B in Canaan with updated reviews, rates, and availability.

The Cornell Inn, Lenox
Exterior

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1000)
"My room was adorable...completely charming and well appointed. I appreciated the phone call with detailed late check-in instructions and when I arrived the property manager walked me to my room. Breakfast was lovely and the staff very friendly. Town a is an easy walk."
The price is AED 448
AED 526 total
includes taxes & fees
26 Jan - 27 Jan
The Cornell Inn, Lenox
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (239)
"Amazing breakfast!"
The price is AED 463
AED 543 total
includes taxes & fees
24 Jan - 25 Jan
Lakehouse Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (362)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is AED 698
AED 779 total
includes taxes & fees
29 Jan - 30 Jan
Chambery Inn
Wilder House Berkshires
Breakfast meal

Wilder House Berkshires

2.0 star property
10.0 out of 10, Exceptional, (14)
"I had a wonderful stay here! I felt very safe and very clean, the room smelled so nice and the bed was very comfortable. The floors are a bit creaky but it just comes with the character of the house. It’s such a great vibe, beautifully decorated and the snacks and coffee are great"
The price is AED 581
AED 648 total
includes taxes & fees
26 Jan - 27 Jan
Wilder House Berkshires
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
24 Jan - 25 Jan
Tanglewood Suites
33 Main
Room

33 Main

4.0 star property
10.0 out of 10, Exceptional, (69)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is AED 1,337
AED 1,493 total
includes taxes & fees
26 Jan - 27 Jan
33 Main
Granville House
Room

Granville House

3.0 star property
10.0 out of 10, Exceptional, (81)
"Lovely place with lovely hosts. The property is eclectic and wonderfully decorated with a very cool common area. Highly recommend "
The price is AED 826
AED 923 total
includes taxes & fees
26 Jan - 27 Jan
Granville House
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (406)
"Beautiful inn. It was nice and quiet, exactly what I needed. "
The price is AED 386
AED 423 total
includes taxes & fees
26 Jan - 27 Jan
Shaker Mill Inn
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (121)
"Great location "
The price is AED 1,025
AED 1,145 total
includes taxes & fees
26 Jan - 27 Jan
Devonfield Inn B&B
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (149)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is AED 698
AED 780 total
includes taxes & fees
24 Jan - 25 Jan
Brook Farm Inn
Inn at Silver Maple Farm
Front of property

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (80)
"Everything "
The price is AED 511
AED 551 total
includes taxes & fees
24 Jan - 25 Jan
Inn at Silver Maple Farm
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"Very enjoyable stat."
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
Interior

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
Whistler's Inn Bed & Breakfast
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 1,559
AED 1,885 total
includes taxes & fees
26 Jan - 27 Jan
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
24 Jan - 25 Jan
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
24 Jan - 25 Jan
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Inn at Kenmore Hall
Front of property

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
The price is AED 1,561
AED 1,712 total
includes taxes & fees
24 Jan - 25 Jan
Inn at Kenmore Hall
Harbour House Inn
Room

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is AED 944
AED 998 total
includes taxes & fees
27 Jan - 28 Jan
Harbour House Inn
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
27 Jan - 28 Jan
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Eastgate Inn B&B
Front of property

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Lovely Inn and Innkeeper. The room was clean and cozy. There was hot coffee and breakfast in the morning including homemade breads and fruit. We will be back! "
Eastgate Inn B&B
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.
Don't see what you're looking for?
See all available properties in Canaan
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Canaan

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1757)
"It had a great pool and hot tub. also right near the ski area, jiminey Peak."
The price is AED 689
AED 792 total
includes taxes & fees
26 Jan - 27 Jan
Vacation Village in the Berkshires
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, (33)
"We had a wonderful stay for our mother’s birthday with her 4 children and 10 of her 12 grandchildren. There was plenty to do for everyone especially with a 75 year difference in ages!!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (235)
"Very lovely place to stay. Everything was clean and the owner made everything simple."
The price is AED 551
AED 833 total
includes taxes & fees
26 Jan - 27 Jan
Berkshire Village Carriage House - Super Private!!
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?
Whether you’re on a family vacation and want a small, cozy place to stay, or you’re traveling solo and hoping to meet fellow tourists, a B&B might be the right choice for your trip. When you want to explore some attractions in town, Queechy Lake and Hollow FIelds Reserve are worth a stop.
Are you thinking about a B&B for your stay?
With attentive service, opportunities to mingle with other guests, and breakfast served on site, B&Bs offer a unique environment.
What are the best B&Bs in Canaan?
Here are some B&Bs in the area: The Cornell Inn, Lenox: 9 mi (14.5 km) from the heart of Canaan. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 11.1 mi (17.9 km) from the downtown core. Enjoy the free full breakfast and deli. Chambery Inn: 9 rooms. Situated 12.3 mi (19.7 km) from the heart of Canaan. Enjoy the private yard and deli. Shaker Mill Inn: 9 rooms. 6.6 mi (10.6 km) from the heart of downtown.Brook Farm Inn: 15 rooms. Located 9 mi (14.5 km) from the core of Canaan. Enjoy the free cooked breakfast and outdoor pool.
What's the best time of year to book my B&B in Canaan?
When you’re dreaming of a getaway to 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 66°F, while the coldest months are January and February with an average of 27°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?
Spend some time exploring Queechy Lake and Hollow FIelds Reserve if you’re hoping to see some of the area’s natural features. You might put Hand Hollow State Forest and Bates Memorial State Park 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 8 mi (12.9 km) away from the city center. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 15.8 mi (25.4 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.