Browse the Best Canaan Resorts from CA $105

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

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Recommended hotels in Canaan

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

1. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Prasanna

CA $139 total

includes taxes & fees

Sep 9 - Sep 10

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

2. Inn at Silver Maple Farm

East Chatham

Erdem

CA $355 total

includes taxes & fees

Sep 8 - Sep 9

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

3. The Yankee Inn

Lenox

Karen

CA $163 total

includes taxes & fees

Sep 28 - Sep 29

4. Berkshire Travel Lodge

Austerlitz

Kris

CA $105 total

includes taxes & fees

Sep 13 - Sep 14

A wooden deck with white railings and hanging flower baskets.

5. Chatham Travel Lodge

Old Chatham

Andrew

CA $173 total

includes taxes & fees

Sep 8 - Sep 9

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

6. Shaker Mill Inn

West Stockbridge

Mervin

CA $224 total

includes taxes & fees

Sep 8 - Sep 9

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

7. Howard Johnson by Wyndham Lenox

Lenox

irene

CA $121 total

includes taxes & fees

Sep 7 - Sep 8

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

8. Berkshire Mountain Lodge

Pittsfield

Robert

CA $154 total

includes taxes & fees

Oct 1 - Oct 2

A group of people performing yoga in an outdoor setting with grass and trees.

9. Pleasant Valley Motel West Stockbridge

West Stockbridge

James

CA $113 total

includes taxes & fees

Sep 7 - Sep 8

A spacious hotel lobby with multiple seating areas, large windows, and a television.

10. Hampton Inn & Suites Berkshires-Lenox

Lenox

Nancy

CA $186 total

includes taxes & fees

Sep 13 - Sep 14

An indoor swimming pool with clear water, tiled floors, and a blue wall.

11. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Steve

CA $196 total

includes taxes & fees

Sep 10 - Sep 11

12. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Debra

CA $182 total

includes taxes & fees

Sep 9 - Sep 10

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

13. Berkshires Untold

Lenox

David

CA $203 total

includes taxes & fees

Sep 8 - Sep 9

A spacious kitchen with wooden flooring, a dining area with a table and chairs, a black sofa, and a television mounted on the wall.

14. NEW RENO - Historic Loft w/views of the Berkshires

New Lebanon

John

CA $317 total

includes taxes & fees

Sep 14 - Sep 15

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

15. Berkshire Inn

Pittsfield

Ellen

CA $129 total

includes taxes & fees

Oct 7 - Oct 8

A large house with a covered patio area featuring outdoor seating and a fire pit.

16. The Whitlock

Lenox

Constance

CA $222 total

includes taxes & fees

Sep 8 - Sep 9

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

17. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

James

CA $197 total

includes taxes & fees

Sep 27 - Sep 28

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

18. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

CA $301 total

includes taxes & fees

Sep 13 - Sep 14

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

19. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

CA $226 total

includes taxes & fees

Sep 10 - Sep 11

20. Quality Inn Lee - Lenox South

Lee

Christine

CA $156 total

includes taxes & fees

Sep 27 - Sep 28

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Top Canaan Hotel Reviews

FairBridge Inn Express

8/10 Good

"great value"

The Whitlock

10/10 Excellent

"The Inn was quaint and conveniently situated in downtown Lenox near shops and restaurants and a short drive to Tanglewood. The virtual check-in worked seamlessly, and a friendly, helpful staff member greeted us at the front desk. Our King Room was clean, comfortable and attractive - perfect for our overnight getaway."

Hotel On North

10/10 Excellent

"Beautiful boutique hotel. Our room was very large with a sitting area + TV. Bed room area equally as large, also with a TV. The bathroom was gorgeous with thoughtful touches. On the marble counter was a makeup mirror with a stool so one could sit. Parking lot was in rear of hotel, secure and easy access to the lobby. Staff couldn't have been more accessible and pleasant. Highly recommend this hotel"

Berkshire Mountain Lodge

10/10 Excellent

"We were there for a one night stay after a show at Tanglewood. Being able to check in online in advance was excellent and saved us a lot of time. There were three of us traveling (a couple and a family member) so we requested a suite. It was huge, well appointed and so clean. The cost was incredibly reasonable for the amount of space we had! The king bed in its own bedroom was super comfortable, and the pull out couch did the job. We didn’t use any of the extra amenities, but saw a few families with children. Lots of space to roam and wander, both inside and on the property. It was an easy 15 minute drive to Tanglewood, so the location worked great for us. The only negative comment would be there was no do not disturb tag for the door, so housekeeping arrived an hour before checkout and we had to send them away. We will stay again if we are in the area, highly recommended!"

Find out more about Canaan

Canaan Resorts information

Number of reviews	8,418
Accommodation	12 Resorts
Lowest Price	CA $105
Highest Price	CA $355

Frequently asked questions

What can I expect from a resort vacation in Canaan?

You deserve a getaway, and a resort is just the place to indulge in all the services and amenities you need for a relaxing time in Canaan. One of the comfortable resorts in the area could be just what you're searching for, whether you want an amazing pool, shopping possibilities, or activities for the kids.

What's a favorite resort in Canaan?

Our highest-rated resorts around Canaan: COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 12.7 mi (20.5 km) from Canaan. Has ski-in/ski-out access, a fitness center, and beach sun loungers. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 12.8 mi (20.5 km) from Canaan. Enjoy the ski-in/ski-out access, fitness center, and garden. Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort - Situated just a 5-minute walk from Jiminy Peak Mountain Resort. 12.9 mi (20.7 km) from Canaan. Access to a fitness center, an indoor pool, and an outdoor pool.

What can I do in Canaan?

Queechy Lake, Hollow FIelds Reserve, and Hand Hollow State Forest are a few of the interesting sights to visit. Other attractions in the area include Bates Memorial State Park and Hancock Shaker Village.

What's the weather like in Canaan?

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's the best way to get to and around Canaan?

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 8 mi (12.9 km) from the city center. You can also search 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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Recommended hotels in Canaan

1. Best Western Plus Berkshire Hills Inn & Suites

2. Inn at Silver Maple Farm

3. The Yankee Inn

4. Berkshire Travel Lodge

5. Chatham Travel Lodge

6. Shaker Mill Inn

7. Howard Johnson by Wyndham Lenox

8. Berkshire Mountain Lodge

9. Pleasant Valley Motel West Stockbridge

10. Hampton Inn & Suites Berkshires-Lenox

11. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

12. Holiday Inn & Suites Pittsfield-Berkshires by IHG

13. Berkshires Untold

14. NEW RENO - Historic Loft w/views of the Berkshires

15. Berkshire Inn

16. The Whitlock

17. The Black Swan Lee - Lenox, an Ascend Collection Hotel

18. Courtyard by Marriott Lenox Berkshires

19. Hilton Garden Inn Lenox Pittsfield

20. Quality Inn Lee - Lenox South

Top Canaan Hotel Reviews

FairBridge Inn Express

Vacation Village in the Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Whitlock

Hotel On North

Quality Inn Lee - Lenox South

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Berkshire Mountain Lodge

Pocketbook Hotel and Bath

Find out more about Canaan

Canaan Resorts information

Frequently asked questions

Explore a world of travel with Expedia

Search Resort Hotels in Canaan from CA $105

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Canaan

1. Best Western Plus Berkshire Hills Inn & Suites

2. Inn at Silver Maple Farm

3. The Yankee Inn

4. Berkshire Travel Lodge

5. Chatham Travel Lodge

6. Shaker Mill Inn

7. Howard Johnson by Wyndham Lenox

8. Berkshire Mountain Lodge

9. Pleasant Valley Motel West Stockbridge

10. Hampton Inn & Suites Berkshires-Lenox

11. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

12. Holiday Inn & Suites Pittsfield-Berkshires by IHG

13. Berkshires Untold

14. NEW RENO - Historic Loft w/views of the Berkshires

15. Berkshire Inn

16. The Whitlock

17. The Black Swan Lee - Lenox, an Ascend Collection Hotel

18. Courtyard by Marriott Lenox Berkshires

19. Hilton Garden Inn Lenox Pittsfield

20. Quality Inn Lee - Lenox South

Top Canaan Hotel Reviews

FairBridge Inn Express

Find out more about Canaan

Canaan Resorts information

Frequently asked questions

Explore a world of travel with Expedia