Canaan B&B: Find the Best Bed and Breakfast from CA $188

A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.

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Our top choices for Canaan bed & breakfast

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

1. Inn at Silver Maple Farm

East Chatham

Linda

CA $289 total

includes taxes & fees

Nov 23 - Nov 24

A red building with a sign reading "Shaker Mill Inn."

2. Shaker Mill Inn

West Stockbridge

Mahadeva

CA $188 total

includes taxes & fees

Nov 2 - Nov 3

A snow-covered outdoor area with a patio, seating, and a covered dining area.

3. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

CA $247 total

includes taxes & fees

Oct 28 - Oct 29

A garden with a white gazebo, a brick pathway, and various plants and flowers.

4. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

CA $232 total

includes taxes & fees

Oct 24 - Oct 25

5. The Inn at Stockbridge

Stockbridge

Kimberly

CA $601 total

includes taxes & fees

Nov 12 - Nov 13

A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

6. Granville House

Housatonic

Cynthia

CA $397 total

includes taxes & fees

Oct 25 - Oct 26

A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

7. The Red Door B&B

Lee

Anonymous traveller

CA $392 total

includes taxes & fees

Oct 26 - Oct 27

A two-story house with a brick entrance and a white facade.

8. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

Philippe

CA $578 total

includes taxes & fees

Nov 7 - Nov 8

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Top Canaan Hotel Reviews

Jiminy Peak Mountain Resort

8/10 Good

"The rooms are outdated but they were clean. The hot tubs were down unfortunately which was one reason we booked this resort so that was a bummer but the staff was great and the price was right. The views were gorgeous and it's near hiking trails and a bike trail. Would book it again if they update their rooms and amenities."

Berkshires Untold

10/10 Excellent

"The lobby was absolutely beautiful, aesthetically and structurally! From all the greenery from the plants to the high ceilings, cute seating areas, and nice bar. The outdoor furniture was a plus, especially with the fire pits and the surrounded by the nice view of the berkshires. After an evening out, we came back and played a board game in the lobby and even did a little painting of our own while enjoying some good cocktails…you can definitely create a vibe. The room was clean, and overall it was a great stay if you’re just looking to relax, unwind, and get away for a bit!"

Berkshire Mountain Lodge

10/10 Excellent

"We've stayed at Berkshire Mountain Lodge in October a number of times now, and we really enjoy the property. The rooms are well-appointed, very clean, and quite comfortable. We appreciate the free washers and dryers as well as the many other amenities, and you cannot beat the location. There's a supermarket down the driveway and across the street and an excellent specialty grocer--Guido's Market--just down the road. We highly recommend this property. The District Restaurant in Pittsfield is excellent. We've also seen several great plays at Barrington Theatre Company. The area is loaded with historical and cultural activities. We like the proximity to Lenox and the Edith Wharton mansion as well as The Clark art museum in Williamstown, both of which have lovely grounds/gardens typically exhibiting sculptures. There are also abundant outdoor activities and opportunities for hiking and lovely scenic drives. This was a good year for fall color, and the red maples were glorious! It's a short ride to Vermont where we checked out Mt. Equinox for the first time. Highly recommend the drive to the top on a sunny, clear day."

Find out more about Canaan

Canaan B&B information

Number of reviews	2,896
Accommodation	35 B&B
Lowest Price	CA $188
Highest Price	CA $862

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. Inn at Silver Maple Farm: 11 rooms. 0.9 mi (1.5 km) from the downtown core. Enjoy the free buffet breakfast and designer toiletries. Shaker Mill Inn: 9 rooms. Situated 6.6 mi (10.6 km) from the heart of Canaan. Chambery Inn: 9 rooms. Located 12.3 mi (19.7 km) from the core of Canaan. Enjoy the private yard and deli.

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.

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Room 1

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Treat yourself

Be picky

Check prices for these dates

Our top choices for Canaan bed & breakfast

1. Inn at Silver Maple Farm

2. Shaker Mill Inn

3. The Cornell Inn, Lenox & The Berkshires

4. Whistler's Inn Bed & Breakfast

5. The Inn at Stockbridge

6. Granville House

7. The Red Door B&B

8. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

9. Chambery Inn

10. Experience Timeless Elegance in The Edith Wharton Room!

11. Devonfield Inn B&B

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

13. Brook Farm Inn

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

15. Cozy Carriage House room with a double bed and private balcony

16. Historic Susan B. Anthony Room - Cozy & Charming Stay

17. Wilder House Berkshires

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

19. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

20. Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Top Canaan Hotel Reviews

Jiminy Peak Mountain Resort

Berkshires Untold

Quality Inn Lee - Lenox South

Berkshire Mountain Lodge

The Whitlock

The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

Quality Inn Great Barrington

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Canaan

Canaan B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find a Bed and Breakfast in Canaan from CA $188

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Canaan bed & breakfast

1. Inn at Silver Maple Farm

2. Shaker Mill Inn

3. The Cornell Inn, Lenox & The Berkshires

4. Whistler's Inn Bed & Breakfast

5. The Inn at Stockbridge

6. Granville House

7. The Red Door B&B

8. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

9. Chambery Inn

10. Experience Timeless Elegance in The Edith Wharton Room!

11. Devonfield Inn B&B

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

13. Brook Farm Inn

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

15. Cozy Carriage House room with a double bed and private balcony

16. Historic Susan B. Anthony Room - Cozy & Charming Stay

17. Wilder House Berkshires

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

19. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

20. Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Top Canaan Hotel Reviews

Jiminy Peak Mountain Resort

Find out more about Canaan

Canaan B&B information

Frequently asked questions

Explore a world of travel with Expedia