Canaan, CT

Travel Guide

A red bridge over a river with snow patches and dry grass.
A stone tower surrounded by lush greenery and trees.
A waterfall cascading over rocks, a small building, and a forested hillside.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is ¥23,968 per night from Jul 8 to Jul 9
¥23,968
¥34,008 total
Jul 8 - Jul 9
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! (1,003 reviews)
"Staff"

Reviewed on Jun 27, 2026

The Red Lion Inn
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
Fully refundable
The price is ¥26,524 per night from Jul 22 to Jul 23
¥26,524
¥32,794 total
Jul 22 - Jul 23
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! (919 reviews)
"Very much enjoyed our stay. Spacious and with all the amenities to let you have a nice independent stay. A nice value and I would book it again."

Reviewed on Jun 29, 2026

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

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
The price is ¥21,383 per night from Jul 5 to Jul 6
¥21,383
¥23,885 total
Jul 5 - Jul 6
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! (1,008 reviews)
"Very clean"

Reviewed on Jun 29, 2026

Quality Inn Great Barrington
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! (18 reviews)
"We thoroughly enjoyed our stay. The house was very comfortable and convenient. We loved Studley, the resident cat - such a sweetheart."

Reviewed on Jun 29, 2026

Cozy Riverside Berkshires Retreat
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

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! (248 reviews)
"Place was very clean and had everything you need. Nice location, very quiet and love the screen porch."

Reviewed on Jun 20, 2026

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Becket MA
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and patios. Popular attractions Pyramid Lake and Iroquis Waterfront are located nearby.
10/10 Exceptional! (5 reviews)
"My family and I had a wonderful stay at Nicole’s A-Frame. The cabin was cozy and inviting, and our kids especially loved the loft. The welcome snacks were such a thoughtful touch! We'd love to return!"

Reviewed on Dec 3, 2025

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use 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.

Stay near popular Canaan attractions

Cities near Canaan