Book Holiday Homes in Canaan

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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
Holiday Homes
Lowest Price
NZ$168
Highest Price
NZ$311
Popular accommodation
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, The Red Lion Inn, Quality Inn, Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

Top trending hotels in Canaan

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundable
The price is NZ$261 per night from 3 Feb to 4 Feb
NZ$261
includes taxes & fees
3 Feb - 4 Feb
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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 NZ$311 per night from 18 Feb to 19 Feb
NZ$311
includes taxes & fees
18 Feb - 19 Feb
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
The Red Lion Inn
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 NZ$168 per night from 9 Feb to 10 Feb
NZ$168
includes taxes & fees
9 Feb - 10 Feb
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 ...
Quality Inn
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Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Fully refundable
The price is NZ$248 per night from 6 Feb to 7 Feb
NZ$248
includes taxes & fees
6 Feb - 7 Feb
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
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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.