North Canaan Holiday Rentals
Check North Canaan holiday rental availability
Holiday Rentals in North Canaan
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Private Estate, Heated YEARROUND Outdoor Pool
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Private Island - Largest Fresh Water Reservoir in Mass....
Perfect Vacation Get Away - Historical New Marlborough
Berkshires Cabin 2 Mi to Appalachian Trail!
Tranquil 3-BR Waterfront Retreat
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Serene Acreage - Pond - Hiking Trails Nearby
The Blue Elm - A Historic Berkshire Cottage
The Meadows House @ Otis Ridge w/ 7-person hot tub
Quintessential 6-BR Berkshires Lodge
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Stockbridge Home, Come Experience The Berkshires!
Other types of properties in North Canaan you may be interested in
Blackberry River Inn
Locust Tree Bed and Breakfast LLC
The Red Lion Inn
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our North Canaan holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up North Canaan. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in North Canaan. Seeing all the best attractions is bound to make you fall in love with North Canaan. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in North Canaan short-term rentals, that won’t be hard to do.
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