Book Holiday Homes in East Canaan

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Featured Holiday Homes in East Canaan

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

East Otis
With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from County Beach.
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Mountain View Getaway

Mountain View Getaway

West Cornwall
Located in Cornwall, this vacation home is on a lake, within a 15-minute drive of Music Mountain and West Cornwall Covered Bridge.
Mountain View Getaway
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.
Spectacular views and close to Great Barrington.
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Peace and quiet on the lake

Peace and quiet on the lake

Becket
With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Peace and quiet on the lake
Lakeside Retreat Just You, The Lake & The View!

Lakeside Retreat Just You, The Lake & The View!

Great Barrington
Located in Great Barrington, this vacation home is on the waterfront, within a 10-minute drive of Art et Industrie and Housatonic River.
Lakeside Retreat Just You, The Lake & The View!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville
The price is AU$552 per night from 16 Apr to 17 Apr
AU$552
includes taxes & fees
16 Apr - 17 Apr
With a stay at this vacation home in Copake Lake, you'll be within a 5-minute drive of Copake Lake and Mosquito Island.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
The Race Mountain House

The Race Mountain House

2 out of 5
Sheffield
Located in Sheffield, this vacation home is in the mountains, within a 10-minute drive of Mount Riga State Park and Drury Preserve.
The Race Mountain House
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
The price is AU$729 per night from 3 Apr to 4 Apr
AU$729
includes taxes & fees
3 Apr - 4 Apr
Located in Sheffield, this vacation home is in a rural location, within a 5-minute drive of Lime Kiln Farm Wildlife Sanctuary and Drury Preserve.
Cheerful 3-bedroom cottage with woodstove
Perfect Nature Retreat In Great Barrington

Perfect Nature Retreat In Great Barrington

2 out of 5
Great Barrington
With a stay at this vacation home in Great Barrington, you'll be within a 5-minute drive of Mahaiwe Performing Arts Center and Housatonic River Walk.
Perfect Nature Retreat In Great Barrington
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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.

East Canaan Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our East Canaan vacation homes are the perfect way for you to wing it.

Holiday houses in East Canaan let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of East Canaan in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local East Canaan adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in East Canaan with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of East Canaan vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

East Canaan Holiday Homes essential information

Accommodation
335 Holiday Homes
Lowest Price
AU$119
Highest Price
AU$729
Popular accommodation
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi, Mountain View Getaway, Spectacular views and close to Great Barrington., Peace and quiet on the lake, Lakeside Retreat Just You, The Lake & The View!, COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, The Race Mountain House, Cheerful 3-bedroom cottage with woodstove, Perfect Nature Retreat In Great Barrington

Top trending hotels in East Canaan

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3 out of 5
131 East Canaan Road, PO Box 664, East Canaan, CT
Fully refundableReserve now, pay when you stay
The price is AU$192 per night from 3 Apr to 4 Apr
AU$192
includes taxes & fees
3 Apr - 4 Apr
Located in East Canaan, Locust Tree Bed and Breakfast LLC is within a 5-minute drive of Lawrence Field and Beckley Furnace Industrial Park.
Locust Tree Bed and Breakfast LLC
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 AU$234 per night from 3 Apr to 4 Apr
AU$234
includes taxes & fees
3 Apr - 4 Apr
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is AU$280 per night from 14 Apr to 15 Apr
AU$280
includes taxes & fees
14 Apr - 15 Apr
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic ...
The Red Lion Inn
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Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 16 Apr to 17 Apr
AU$119
includes taxes & fees
16 Apr - 17 Apr
With a stay at Quality Inn in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 7 minutes by foot from ...
Quality Inn
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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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^Subject to availability and chosen travel dates.