Canaan, CT
Travel Guide
Visit Canaan
The Red Lion Inn
30 Main Street Stockbridge MA
$228 nightly
The price is $254 total per night from Aug 24 to Aug 25
$254 total
Aug 24 - Aug 25
Total with taxes and 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! (1,001 reviews)
"Needs updating and cleaning.Pool ate in very bad shape"
Reviewed on Jul 30, 2026
Quality Inn Great Barrington
372 Main Street Great Barrington MA
$118 nightly
The price is $132 total per night from Aug 23 to Aug 24
$132 total
Aug 23 - Aug 24
Total with taxes and 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! (1,003 reviews)
"The property was clean and the front staff amazing! My complaint was with housekeeping. They came knocking early in the morning when we were still sleeping. They never came back all 3 days. I was shocked for 3 days no cleaning or replenishing toilet paper, trash pick up, etc."
Reviewed on Jul 29, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$152 nightly
The price is $169 total per night from Aug 31 to Sep 1
$169 total
Aug 31 - Sep 1
Total with taxes and 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! (946 reviews)
"Room was dated.. bathtub in primary bedroom had mold and mildew!"
Reviewed on Jul 28, 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.
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 Monument Mountain Reservation and Art ...
Lakefront Summer Stunner in New England Just 2 Hours From NYC
Sharon CT
Stay at this vacation home in Sharon. Enjoy free WiFi, a garden, and patios. Popular attractions Indian Lake and Veterans Field are located nearby.
10/10 Exceptional! (96 reviews)
"This was our second consecutive year staying here for a week in July. The cottage is very comfortable, and we enjoyed boating, biking, hiking, and exploring Sharon and Millerton. The amazing views of the water and the hills never get old!"
Reviewed on Jul 27, 2026
Charming 1870 cape cottage in Litchfield
Litchfield CT
Stay at this vacation home in Litchfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions White Memorial Conservation Center and Bantam ...
10/10 Exceptional! (73 reviews)
"Beautiful,clean,comfortable and quiet"
Reviewed on Jul 26, 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.
Stay near popular Canaan attractions
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- Visit Morris
- Visit Bantam
- Visit East Canaan
- Visit New Haven
- Visit Colebrook
- Visit Connecticut
- Visit Canann Village Historic District
- Visit Salisbury
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- Visit Cornwall Bridge
- Visit Milton Center Historic District
- Visit Torrington
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- Visit Riverton
- Visit West Cornwall
- Land of Nod Vineyard and Winery
- East Canaan Vacations
- Visit Litchfield Historic District
- Visit Kent
- Visit Lime Rock
- Visit Norfolk
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- Visit Winsted
- Visit Harwinton
- Visit Lakeville
- Visit Warren
- Visit New Preston
- Visit Falls Village
- Visit East Hartland
- Visit City Meadow Boardwalk
- Lime Rock Park
- National Shrine of the Divine Mercy
- Lee Premium Outlets
- Norman Rockwell Museum
- Lake Waramaug State Park
- Jacob's Pillow
- Mohawk Mountain Ski Area
- Taconic State Park
- Ski Butternut
- Kent Falls State Park
- Catamount Ski Area
- Lake Taghkanic State Park
- Lake Waramaug
- Millbrook Vineyards and Winery
- Harlem Valley Rail Trail
- Catamount Aerial Adventure Park
- Wing's Castle
- Music Mountain
- Otis Reservoir
- Berkshire Botanical Garden
- Mahaiwe Performing Arts Center
- Infinity Music Hall and Bistro
