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

Best Resorts in Canaan

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13
No exact matches found, but these alternatives could be just right

Recommended hotels in Canaan

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

1. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
$174 nightly
The price is $195
Nov 8 - Nov 9
Total with taxes and fees
Inn at Silver Maple Farm
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

2. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,004 reviews)
"Room was spacious and clean"
United States
James
$93 nightly
The price is $104
Nov 1 - Nov 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Outdoor pool

3. Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (518 reviews)
"Perfect as I was just needing a place to stay overnight."
United States
Kris
$75 nightly
The price is $84
Oct 15 - Oct 16
Total with taxes and fees
Berkshire Travel Lodge
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

4. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,010 reviews)
"The location was good for our trip."
United States
Basil
$106 nightly
The price is $118
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A red building with a sign reading "Shaker Mill Inn."

5. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (477 reviews)
"Very nice Inn in West Stockbridge. Easy walk to center of town and short drive to all the Berkshires attractions. Room was very quiet and the grounds are wonderful. Highly recommended!"
United States
Steven
$131 nightly
The price is $144
Nov 9 - Nov 10
Total with taxes and fees
Shaker Mill Inn
A group of people performing yoga in an outdoor setting with grass and trees.

6. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The best aspect of this motel is the price. It is very close to the Tanglewood concert space and in West Stockbridge, a quaint town with galleries, a good bookstore, the excellent Turnpark Outdoor Sculpture Garden and "Amici" a nice Italian restaurant, etc."
United States
James
$69 nightly
The price is $76
Oct 15 - Oct 16
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
A wooden deck with white railings and hanging flower baskets.

7. Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (250 reviews)
"I had a very nice stay. The staff was friendly and helpful and my room was clean and comfortable. This hotel was conveniently located for my needs and I’d stay here again. The owner is a lovely lady."
United States
andrew
$112 nightly
The price is $125
Oct 15 - Oct 16
Total with taxes and fees
Chatham Travel Lodge
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

8. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (668 reviews)
"Nice hotel."
United States
Tracy
$126 nightly
The price is $140
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (237 reviews)
"Very nice rooms, staff friendly."
United States
Ginger
$99 nightly
The price is $111
Nov 12 - Nov 13
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A spacious hotel lobby with multiple seating areas, large windows, and a television.

10. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"Breakfast was great"
United States
Thomas
$110 nightly
The price is $122
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

11. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (924 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Oct 18 - Oct 19
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A hotel patio with outdoor seating and a fire pit.

12. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (713 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$128 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

13. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,205 reviews)
"Friendly hotel staff."
United States
Kathleen
$125 nightly
The price is $139
Nov 3 - Nov 4
Total with taxes and fees
Berkshire Mountain Lodge
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

14. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,037 reviews)
"A very good place to stay"
United States
Madhavi R
$136 nightly
The price is $152
Nov 1 - Nov 2
Total with taxes and fees
Berkshires Untold
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

15. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (423 reviews)
"Large, clean, comfortable suite."
United States
Rena
$99 nightly
The price is $111
Oct 15 - Oct 16
Total with taxes and fees
The Central Downtown Inn & Suites
A spacious kitchen with wooden flooring, a dining area with a table and chairs, a black sofa, and a television mounted on the wall.

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

NEW RENO - Historic Loft w/views of the Berkshires
New Lebanon
9.6 out of 10, Exceptional, (15 reviews)
"Place was nice, decent value, comfy and cozy. Would stay again."
United States
John
$237 nightly
The price is $240
Nov 3 - Nov 4
Total with taxes and fees
NEW RENO - Historic Loft w/views of the Berkshires
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

17. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (45 reviews)
"Stay was nice"
United States
Kirsty
$143 nightly
The price is $160
Nov 8 - Nov 9
Total with taxes and fees
Element by Marriott Lenox Berkshires
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
$115 nightly
The price is $128
Nov 8 - Nov 9
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Room

19. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,000 reviews)
"enjoyed our stay"
United States
Mark
$103 nightly
The price is $115
Nov 13 - Nov 14
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A building entrance with a large planter with purple flowers and a small tree.

20. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (950 reviews)
"Great place!"
United States
Lawrence
$149 nightly
The price is $166
Nov 1 - Nov 2
Total with taxes and fees
Hotel On North
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Canaan Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"This is a gem of a small hotel/motel. Super comfortable rooms, updated bathrooms, and well done self serve breakfast included. Also has an indoor pool and an outdoor pool during the season. And a very nice hiking trail off of the back. An excellent change from the Run of the middle courtyard Marriott!"
Kimberly 2-night trip
Posted 10 hours ago
The Yankee Inn

Find out more about Canaan

Canaan Resorts information

Number of reviews
9,553
Accommodation
8 Resorts
Lowest Price
$76
Highest Price
$240

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: 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. Has ski-in/ski-out access, a fitness center, and a garden. COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 12.7 mi (20.5 km) from Canaan. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 12.9 mi (20.7 km) from Canaan. Access to ski-in/ski-out access, a fitness center, and an indoor 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.

Explore a world of travel with Expedia