Canaan
Travel Guide
Visit Canaan
The Red Lion Inn
30 Main Street Stockbridge MA
The price is CA $214 per night from Sep 30 to Oct 1
CA $214
CA $308 total
Sep 30 - Oct 1
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,007 reviews)
"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"
Reviewed on Sep 2, 2026
Quality Inn Great Barrington
372 Main Street Great Barrington MA
The price is CA $129 per night from Sep 23 to Sep 24
CA $129
CA $144 total
Sep 23 - Sep 24
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,001 reviews)
"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked ..."
Reviewed on Sep 2, 2026
Holiday Inn Club Vacations Oak 'n Spruce Resort
190 Meadow Street South Lee MA
The price is CA $143 per night from Sep 7 to Sep 8
CA $143
CA $186 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this ski hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. ...
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.
Summer Lake Cottage, private beach, Berkshire Hills, small village
Lakeville CT
Stay at this cottage in Lakeville. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Holley-Williams House Museum and Gay Woods Hill are located ...
The Meadows House @ Otis Ridge w/ 7-person hot tub
Otis MA
Stay at this vacation home in Otis. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Otis Ridge and Old Baldy Wildlife Sanctuary are located ...
9.8/10 Exceptional! (48 reviews)
"Lars was extremely accommodating and great with communication. The home was everything we needed for a little getaway with the kids. Little back yard was fun for the kids despite the meadow. It was extremely peaceful and we even saw some deer. The hot tub was super relaxing at the end of the day. ..."
Reviewed on Aug 15, 2026
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Becket MA
Stay at this cabin in Becket. Enjoy a garden, laundry facilities, and furnished lanais. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (258 reviews)
"Great location for our visit to Jacob’s Pillow. Quiet spot and loved the screen porch."
Reviewed on Aug 31, 2026
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.
