North Canaan Vacation Rentals
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check North Canaan vacation rental availability
Vacation Rentals in North Canaan
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
10.0 out of 10, Exceptional, (3)
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
Save an average of 15% on thousands of hotels when you're signed in
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
The price is ¥24,923
¥52,439 total
includes taxes & fees
Jun 30 - Jul 1
Perfect Vacation Get Away - Historical New Marlborough
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
The price is ¥23,513
¥42,582 total
includes taxes & fees
Jun 24 - Jun 25
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
Serene Acreage - Pond - Hiking Trails Nearby
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
Private Estate, Heated YEARROUND Outdoor Pool
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
Private Island - Largest Fresh Water Reservoir in Mass....
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
Beautiful retreat to the woods to enjoy the winter season.
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, (31)
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, (3)
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
10.0 out of 10, Exceptional, (2)
The Blue Elm - A Historic Berkshire Cottage
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (2)
The price is ¥31,350
¥64,785 total
includes taxes & fees
Jun 16 - Jun 17
The Meadows House @ Otis Ridge w/ 7-person hot tub
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (12)
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.
Other types of properties in North Canaan you may be interested in
Blackberry River Inn
Blackberry River Inn
9.4 out of 10, Exceptional, (32)
The price is ¥27,597
¥31,736 total
includes taxes & fees
Jun 13 - Jun 14
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLC
9.0 out of 10, Wonderful, (326)
The price is ¥16,459
¥18,928 total
includes taxes & fees
Jun 10 - Jun 11
The Red Lion Inn
The Red Lion Inn
8.8 out of 10, Excellent, (891)
The price is ¥27,652
¥34,389 total
includes taxes & fees
Jun 17 - Jun 18
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.
Search for holiday rentals in North Canaan on Expedia! You can easily find your home rentals, villas, holiday apartments in North Canaan using one of the methods below:
- View our selection of featured holiday rentals in North Canaan
- Use the map to find apartments and other holiday homes in the North Canaan neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in North Canaan while they last
Look no further and take a look at our great range of rental properties in North Canaan!
Frequently asked questions
Recent reviews of North Canaan propertiesExpedia verified reviews
5/5 Excellent
"Good value"
A verified traveler stayed at Econo Lodge Lee - Great Barrington
Posted 3 days ago