Book Holiday Homes in Canaan

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Featured Holiday Homes in Canaan

Lakefront Luxe: Private Dock, Game Rm, Near Hudson

Lakefront Luxe: Private Dock, Game Rm, Near Hudson

Athens
Located in Coxsackie, this vacation home is on the waterfront, a 1-minute drive from Sleepy Hollow Lake and 6 minutes from Hudson River Islands State Park.
Lakefront Luxe: Private Dock, Game Rm, Near Hudson
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.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$361 per night from 30 Dec to 31 Dec
AU$361
includes taxes & fees
30 Dec - 31 Dec
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
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Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Monterey
Located in Monterey, this vacation home is within a 5-minute drive of Beartown State Forest and Bidwell House Museum.
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Beautiful Berkshire Farm House on 160+ Acres

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington
Located in Great Barrington, this vacation home is on the waterfront, within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts ...
Beautiful Berkshire Farm House on 160+ Acres
Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

Egremont
With a stay at this vacation home in Great Barrington, you'll be within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts ...
Private Estate, Heated Yearround Outdoor Pool
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

Becket
When you stay at this vacation home in Becket, you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Quintessential 6-BR Berkshires Lodge
3 Bedroom Lakefront Home with Hot Tub & Fireplace

3 Bedroom Lakefront Home with Hot Tub & Fireplace

Wynantskill
Located in Wynantskill, this vacation home is on the waterfront, within a 10-minute drive of Kinloch Park Dog Park and Joseph L Bruno Stadium.
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Wyndhurst Golf & Club and Berkshire Scenic Railway Museum.
Amore Estate - beautiful room with many places to explore and relax in.
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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.

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 Canaan vacation homes are the perfect way for you to wing it.

Holiday houses in 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 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 Canaan adventures, obvs.

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

Canaan Holiday Homes essential information

Accommodation
379 Holiday Homes
Lowest Price
AU$151
Highest Price
AU$361
Popular accommodation
Lakefront Luxe: Private Dock, Game Rm, Near Hudson, Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Berkshire Ski House on Lake Garfield w/HT By Great Barrington , Beautiful Berkshire Farm House on 160+ Acres, Private Estate, Heated Yearround Outdoor Pool, Quintessential 6-BR Berkshires Lodge, 3 Bedroom Lakefront Home with Hot Tub & Fireplace, Amore Estate - beautiful room with many places to explore and relax in.

Top trending hotels in Canaan

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 2 Jan to 3 Jan
AU$173
includes taxes & fees
2 Jan - 3 Jan 2025
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$247 per night from 6 Jan to 7 Jan
AU$247
includes taxes & fees
6 Jan - 7 Jan 2025
When you a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 5-minute walk of Housatonic River and Mission House.
The Red Lion Inn
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$159 per night from 5 Jan to 6 Jan
AU$159
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Lenox, Life House Berkshires is within a 15-minute walk of Kennedy Park and Pleasant Valley Wilderness Sanctuary.
Life House Berkshires
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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$151 per night from 5 Jan to 6 Jan
AU$151
includes taxes & fees
5 Jan - 6 Jan 2025
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.