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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

B&B in Canaan

Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is AED 750
AED 793 total
includes taxes & fees
8 Jan - 9 January 2026
Harbour House Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AED 684
AED 802 total
includes taxes & fees
12 Dec - 13 Dec
Lakehouse Inn
Front of property
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

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
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
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 559
AED 625 total
includes taxes & fees
16 Dec - 17 Dec
Wilder House Berkshires
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is AED 392
AED 430 total
includes taxes & fees
10 Dec - 11 Dec
Shaker Mill Inn
Front of property - evening/night
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
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 1,636
AED 1,828 total
includes taxes & fees
5 Jan - 6 January 2026
33 Main
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (88)
"Outstanding all around!"
United States
Jonathan
The price is AED 735
AED 821 total
includes taxes & fees
1 Jan - 2 January 2026
Granville House
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Lenox
The price is AED 995
AED 1,301 total
includes taxes & fees
9 Dec - 10 Dec
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AED 614
AED 706 total
includes taxes & fees
9 Dec - 10 Dec
The Cornell Inn, Lenox & The Berkshires
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
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
9 Dec - 10 Dec
Tanglewood Suites
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

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
5 Jan - 6 January 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Lenox
The price is AED 995
AED 1,301 total
includes taxes & fees
9 Dec - 10 Dec
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony

Lenox
The price is AED 1,116
AED 1,461 total
includes taxes & fees
9 Dec - 10 Dec
Cozy Carriage House room with a double bed and private balcony
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.

Lenox
The price is AED 1,055
AED 1,379 total
includes taxes & fees
9 Dec - 10 Dec
Elegant Carriage House room with a queen bed and private patio.
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
The price is AED 1,177
AED 1,538 total
includes taxes & fees
9 Dec - 10 Dec
Historic Susan B. Anthony Room - Cozy & Charming Stay
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 1,561
AED 1,712 total
includes taxes & fees
16 Dec - 17 Dec
Inn at Kenmore Hall
Fireplace
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Lenox
The price is AED 1,449
AED 1,896 total
includes taxes & fees
10 Dec - 11 Dec
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Lenox
The price is AED 1,570
AED 2,005 total
includes taxes & fees
9 Dec - 10 Dec
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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 Canaan Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Staff is absolutely amazing "
Mitchell 2-night trip
Posted 13 hours ago
Comfort Inn & Suites East Greenbush - Albany

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 & The Berkshires: 9 mi (14.5 km) from the heart of Canaan. Enjoy the free full breakfast and unique décor. Shaker Mill Inn: 9 rooms. 6.6 mi (10.6 km) from the downtown core. Chambery Inn: 9 rooms. Situated 12.3 mi (19.7 km) from the heart of Canaan. Enjoy the private yard and deli. Lakehouse Inn: 14 rooms. 11.1 mi (17.9 km) from the heart of downtown. Enjoy the free full breakfast and deli. Inn at Silver Maple Farm: 11 rooms. Located 0.9 mi (1.5 km) from the core of Canaan. Enjoy the free buffet breakfast and designer toiletries.
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.