COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Search Vacation Homes in Canaan

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Browse Select Canaan Vacation Homes

Modern Lakehouse Retreat , Great for Groups!
3.5 out of 5
Island Drive 7, Copake, NY
Get Rates
Situated in Town of Copake, this vacation home is 0.7 mi (1.1 km) from Callan Family Care and 2.8 mi (4.5 km) from Taconic State Park. Bash Bish Falls State ...
Modern Lakehouse Retreat , Great for Groups!
Beautiful Lakehouse With Pool Table
3 out of 5
3 Island Drive, Copake, NY
Get Rates
Situated in Town of Copake, this vacation home is 0.6 mi (1 km) from Callan Family Care and 2.8 mi (4.5 km) from Taconic State Park. Bash Bish Falls State Park ...
Beautiful Lakehouse With Pool Table
Relaxing 2BR Lakehouse
3.5 out of 5
Island Drive 11, Copake, NY
Get Rates
Situated in Town of Copake, this vacation home is 0.7 mi (1.1 km) from Callan Family Care and 2.8 mi (4.6 km) from Taconic State Park. Bash Bish Falls State ...
Relaxing 2BR Lakehouse
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Plum Guide - The Nook
3 out of 5
99 Island Drive, Copake, NY
Get Rates
Situated in Town of Copake, this vacation home is 0.7 mi (1.1 km) from Callan Family Care and 2.8 mi (4.5 km) from Taconic State Park. Bash Bish Falls State ...
Plum Guide - The Nook
Plum Guide - Mahogany
3.5 out of 5
56 Broadway, Amenia, NY
Get Rates
Situated in a rural location, this vacation home is within 9 mi (15 km) of TriArts Sharon Playhouse, Trevor Zoo, and Sharon Audubon Center. Millbrook Vineyards ...
Plum Guide - Mahogany
Plum Guide - Country Roads
3.5 out of 5
57 Birch Hill Road, Hillsdale, NY
Get Rates
Situated in Hillsdale, this vacation home is within 9 mi (15 km) of Callan Family Care, Catamount Ski Area, and Catamount Aerial Adventure Park. Taconic State ...
Plum Guide - Country Roads
Don't see what you're looking for?
See all available properties in Canaan
View all properties
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 property types in Canaan

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3 out of 5
131 East Canaan Road, PO Box 664, Canaan, CT
The price is NT$2,975 per night from Apr 20 to Apr 21
4.4/5Wonderful! (183 reviews)
"This was our second stay at the Locust Tree. Beautiful grounds, well-maintained inside and out and reasonably priced. Heidi takes good care of her guests, knows the area well and is very personable."

Reviewed on 2020/10/12

Locust Tree Bed and Breakfast LLC
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
The price is NT$2,397 per night from May 3 to May 4
4.4/5Excellent! (114 reviews)
"The staff was nice and helpful and the pool was warm I love it"

Reviewed on 2021/4/4

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Holiday Inn Club Vacations Oak n' Spruce Resort, an IHG Hotel

Holiday Inn Club Vacations Oak n' Spruce Resort, an IHG Hotel

3.5 out of 5
190 Meadow Street, South Lee, MA
The price is NT$3,472 per night from May 3 to May 4
4.4/5Excellent! (145 reviews)
"This is a great place to be able to relax and unwind, especially after this past year. The property is super clean, the beds are comfortable. The views are great and close to shopping and museums."

Reviewed on 2021/3/15

Holiday Inn Club Vacations Oak n' Spruce Resort, an IHG Hotel
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.