Canaan Vacation Rentals
Destination
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 mi
50 rentals in Canaan.
Private Cottage, Come Enjoy Nature!
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Hudson River Valley/Berkshires Rural Retreat
Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Best of the Berkshires & Hudson Valley
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Restored historic farmhouse on 25 private acres
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Berkshire Rural Retreat
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Private home on a Beautiful lake. Large deck for entertaining
Rental Home
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Private Tennis court, hot tub & pool Berkshires 13 acre Estate 4 bedrooms
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Best of the Berkshires & Hudson Valley
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Berkshires Lake House With Private Dock and Chefs Kitche
Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Peaceful Berkshires Year-Round Home - Fabulous mountain and lake views, sunsets
Rental Home
7 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
The following properties within 20 miles of Canaan match all your filters:
Charming Guest Suite
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Affiliated with FlipKey
Cozy Berkshire Hills Home in Close Proximity to Skiing
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Richmond Pond Beauty
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Birds’ Nest Bungalow
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Private apartment in beautiful country barn
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Brand new listing! Dublinshire Farm #3: The crown jewel of a Shaker Barn.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Modern 4 bedroom lakefront house in The Berkshires.
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Newly Renovated Cabin in the Country
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Get away and get back to nature!
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Foggy Bottom Studio
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Escape for the weekend!
Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
New listing, beautiful apartment in historic shaker barn
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Renovated Berkshire Cottage
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Escape from it all. Woods, birds, campfire and fresh air.
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Berkshires Getaway w/ Deck & Mountain Views!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Cottage near TangleWood & ALL Berkshires fun
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
A 200 year old center hall colonial between the Berkshires and the Hudson River
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Caretaker's Cottage: 20 minutes from Tanglewood
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Fog Hill Cabin is a peaceful retreat set in a forest landscape. Stargazing Bliss
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
SAFE AND COZY BERKSHIRES GETAWAY
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Showing results 1-30 of 50
Frequently Asked Questions about Canaan
- Yes, here are some popular vacation rentals in Canaan that have a pool:
- Private Cottage, Come Enjoy Nature!
- Hudson River Valley/Berkshires Rural Retreat
- Best of the Berkshires & Hudson Valley
- Yes, here are some popular vacation rentals in Canaan that have internet access:
- Private Cottage, Come Enjoy Nature!
- Hudson River Valley/Berkshires Rural Retreat
- Best of the Berkshires & Hudson Valley
- Some of the most popular kid friendly rentals in Canaan are:
- Private Cottage, Come Enjoy Nature!
- Hudson River Valley/Berkshires Rural Retreat
- Best of the Berkshires & Hudson Valley
Canaan TourismCanaan HotelsCanaan Bed and BreakfastCanaan Vacation RentalsFlights to CanaanCanaan RestaurantsThings to Do in CanaanCanaan Travel ForumCanaan PhotosCanaan MapCanaan Travel Guide
Things to DoRestaurantsFlightsVacation RentalsTravel StoriesCruisesRental Cars