Canaan, CT

Travel Guide

Red bridge over the Housatonic River
beckley iron furnace north caanan connecticut
Great Falls Summer Landscape Caanan
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is SAR 568 per night from Jul 1 to Jul 2
SAR 568
SAR 802 total
1 Jul - 2 Jul
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! (1,004 reviews)
"Our experience at the Red Lion Inn went beyond our expectations. The entire staff was most helpful, went above and beyond to make our stay enjoyable, and treated us as if we were the only guests staying there! The inn is magnificent and we felt we were staying in a museum! The accommodation was lovely ..."

Reviewed on 20 June 2026

The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
The price is SAR 389 per night from Jun 24 to Jun 25
SAR 389
SAR 434 total
24 Jun - 25 Jun
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! (1,009 reviews)
"Good breakfast"

Reviewed on 20 June 2026

Quality Inn Great Barrington
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
The price is SAR 503 per night from Jun 23 to Jun 24
SAR 503
SAR 635 total
23 Jun - 24 Jun
includes taxes & fees
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
9.2/10 Wonderful! (913 reviews)
"Mini golf was amazing, as was having access to shuffleboard, cornhole and more. And the arcade was great, too, we went back many times! Room was clean and nice with it's own balcony and the resort was calm and quiet."

Reviewed on 19 June 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.
Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions National Shrine of the Divine Mercy and ...
9.4/10 Exceptional! (16 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."

Reviewed on 13 June 2026

Cozy Riverside Berkshires Retreat
Little Longbow Lakefront Chalet

Little Longbow Lakefront Chalet

Becket MA
Book a stay at this family-friendly chalet in Becket. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Pyramid Lake and Jacob's ...
9.8/10 Exceptional! (27 reviews)
"Good location in the berkshires. Property is private and pretty with lots of amenities."

Reviewed on 15 June 2026

Little Longbow Lakefront Chalet
Large Barn styled vacation home that fits groups with space to spare.

Large Barn styled vacation home that fits groups with space to spare.

Craryville NY
Book a stay at this family-friendly vacation home in Copake Lake. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Copake Lake and Mosquito ...
10/10 Exceptional! (76 reviews)
"Home was in the perfect location for a golf weekend"

Reviewed on 8 June 2026

Large Barn styled vacation home that fits groups with space to spare.
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.

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