Photo by Robin/Loving Life

Search Villas in Canaan

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Villas in Canaan

No exact matches found, but these alternatives could be just right

Recommended hotels in Canaan

Exterior
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is SAR 351
SAR 392 total
includes taxes & fees
10 Dec - 11 Dec
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (704)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is SAR 383
SAR 428 total
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Great stay!"
United States
Ann
The price is SAR 335
SAR 374 total
includes taxes & fees
15 Dec - 16 Dec
The Yankee, Trademark Collection by Wyndham
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is SAR 492
SAR 549 total
includes taxes & fees
14 Dec - 15 Dec
Element Lenox Berkshires
Exterior
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is SAR 345
SAR 385 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Monument Mountain Motel

Motel in Great Barrington

2.5 star property
9.0 out of 10, Wonderful, (804)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Garden
Shaker Mill Inn

Bed & Breakfast in West Stockbridge

2.5 star property
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is SAR 388
SAR 426 total
includes taxes & fees
16 Dec - 17 Dec
Shaker Mill Inn
Exterior
Travelodge by Wyndham Great Barrington Berkshires

Motel in Great Barrington

2.0 star property
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is SAR 281
SAR 314 total
includes taxes & fees
9 Dec - 10 Dec
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Quality Inn

Quality Inn

2.5 star property
8.4 out of 10, Very Good, (1001)
"Clean room and good breakfast "
United States
Kelly
The price is SAR 340
SAR 380 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1003)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is SAR 380
SAR 424 total
includes taxes & fees
17 Dec - 18 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Berkshire Mountain Lodge

Lodge in Pittsfield

3.0 star property
9.0 out of 10, Wonderful, (781)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Exterior
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is SAR 364
SAR 406 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is SAR 387
SAR 433 total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn & Suites Berkshires-Lenox
Exterior
Howard Johnson by Wyndham Lenox

Motel in Lenox

2.0 star property
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
The price is SAR 297
SAR 331 total
includes taxes & fees
9 Dec - 10 Dec
Howard Johnson by Wyndham Lenox
Exterior
The Central Downtown Inn & Suites

Guesthouse in Pittsfield

4.0 star property
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is SAR 335
SAR 374 total
includes taxes & fees
9 Dec - 10 Dec
The Central Downtown Inn & Suites
Exterior
Berkshire Inn

Motel in Pittsfield

2.0 star property
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is SAR 300
SAR 335 total
includes taxes & fees
15 Dec - 16 Dec
Berkshire Inn
Exterior
Pleasant Valley Motel West Stockbridge

Motel in West Stockbridge

2.0 star property
6.8 out of 10, (1002)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is SAR 197
SAR 216 total
includes taxes & fees
6 Jan - 7 January 2026
Pleasant Valley Motel West Stockbridge
Exterior
Berkshires Untold

Lodge in Lenox

3.5 star property
9.0 out of 10, Wonderful, (808)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is SAR 412
SAR 460 total
includes taxes & fees
9 Dec - 10 Dec
Berkshires Untold
Exterior
Quality Inn

Quality Inn

2.5 star property
8.4 out of 10, Very Good, (1000)
"Clean room, nice location "
United States
Devron
The price is SAR 284
SAR 317 total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn
Exterior
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2168)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is SAR 334
SAR 414 total
includes taxes & fees
9 Dec - 10 Dec
Vacation Village in the Berkshires
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The roomy and comfortable suite was a step above a typical hotel room. We took advantage of the full kitchen to prepare our own meals. We enjoyed the pool and hot tub. We will definitely consider staying here again at a future trip to the Berkshires."
Richard 3-night trip
Posted 7 hours ago
Berkshire Mountain Lodge