We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday villas in Canaan, NY

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 83 Rentals in the Canaan Area
loading...
Sort by

The following rentals are within 25 kilometers of Canaan, New York.

From
€195
Per Night
View Details
1 / 9
Payment Protection
Valatie
3 Bedrooms, 3 Bathrooms, Sleeps 5
Details Reviews (3) Make Enquiry
From
€148
Per Night
View Details
1 / 12
Payment Protection
Alford, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Enquiry
From
€240
Per Night
View Details
1 / 12
Payment Protection
Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 1
Bookings
Details Reviews (1) Make Enquiry
Also consider
Wyndham Bentley Brook at Jiminy Peak
2 Bedrooms, sleeps 6
€220 - €280 / night
Beautiful Home Richmond Shores
2 Bedrooms, sleeps 6
€80 - €107 / night
Fall/ Winter- Spectacular Setting-Family- Ski Sled Hike Fish Relax
3 Bedrooms, sleeps 8
€401 - €481 / night
the BIG room at chestnut lodge
1 Bedroom, sleeps 6
€160 / night
From
€200
Per Night
View Details
1 / 10
Payment Protection
Great Barrington, MA
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 20 May 2013
This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
See all reviews
From
€120
Per Night
View Details
1 / 14
Payment Protection
Ghent
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 6 August 2013
This was the perfect location for a base camp from which to explore the Hudson River Valley area. We took in a Tanglewood concert (40-minute drive) and explored the backroads full...
See all reviews
From
€361
Per Night
View Details
1 / 17
Payment Protection
Lee, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 12 June 2014
I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
See all reviews
From
€88
Per Night
View Details
1 / 11
Payment Protection
Richmond, MA
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Enquiry
From
€400
Per Night
View Details
1 / 32
Payment Protection
Stockbridge, MA
4 Bedrooms, 4 Bathrooms, Sleeps 12
Bookings
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 18 July 2014
Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and...
See all reviews
Get the List
From
€120
Per Night
View Details
1 / 4
Payment Protection
Lee, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 17 June 2014
And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
See all reviews
From
€240
Per Night
View Details
1 / 25
Payment Protection
Lee, MA
3 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (2) Make Enquiry
From
€128
Per Night
View Details
1 / 35
Payment Protection
North Egremont, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 12 September 2014
I had a wonderful stay! The property is gorgeous and serene. The suite is clean, very nicely decorated and private. Absolutely lovely!
5 of 5 stars Reviewed 4 September 2014
Lovely haven in the bucolic Berkshire countryside . Our suite had everything we could want- privacy, beautiful restful decor, comfort , all in a gorgeous setting. Short drive to...
See all reviews
From
€180
Per Night
View Details
1 / 14
Payment Protection
Hancock, MA
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (3) Make Enquiry
From
€143
Per Night
View Details
1 / 16
Payment Protection
Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 25 October 2014
Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
See all reviews
From
€160
Per Night
View Details
1 / 8
Payment Protection
Lee, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 17 June 2014
We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
See all reviews
From
€183
Per Night
View Details
1 / 4
Payment Protection
Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 11 August 2013
Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
See all reviews
From
€100
Per Night
View Details
1 / 6
Payment Protection
West Stockbridge, MA
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 18 December 2013
We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
See all reviews
From
€116
Per Night
View Details
1 / 16
Payment Protection
Hancock, MA
1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 16 October 2014
This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels...
See all reviews
From
€300
Per Night
View Details
1 / 33
Payment Protection
Lee, MA
5 Bedrooms, 3 Bathrooms, Sleeps 11
Bookings
Details Reviews (8) Make Enquiry
4 of 5 stars Reviewed 27 September 2014
We went there for a golf buddy trip and it was the perfect place for us in the Berkshires. Place was very clean, and had all the comforts of home. Robin is super friendly and...
5 of 5 stars Reviewed 3 September 2014
This is a wonderful home! Robin has taken care with the furnishing and finishings, which are a nice blend of antique and modern. Her love of the home and region is apparent...
See all reviews
From
€200
Per Night
View Details
1 / 12
Payment Protection
West Stockbridge, MA
5 Bedrooms, 2 Bathrooms, Sleeps 12
Bookings
Details Reviews (8) Make Enquiry
5 of 5 stars Reviewed 28 October 2014
Our group of 9 friends stayed here for two nights in late October. Everyone was pleased with the accomodations. The house is close to Stockbridge, Lee, and Lenox. It is nestled in...
5 of 5 stars Reviewed 31 August 2014
We were a group nine. We found the house to have a rustic charm complete with hardwood floors and exposed beams in the walls and ceilings. We tended to congregate in the living...
See all reviews
From
€200
Per Night
View Details
1 / 14
Payment Protection
West Stockbridge, MA
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 2 November 2014
Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
5 of 5 stars Reviewed 25 August 2014
We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
See all reviews
From
€120
Per Night
View Details
1 / 21
Payment Protection
Lenox, MA
4 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (18) Make Enquiry
5 of 5 stars Reviewed 22 October 2014
We spent the weekend at the Gartner House in Lenox to visit my son at Shakespeare and Company. From my first contact with Deb, she was friendly and helpful. It is evident...
4 of 5 stars Reviewed 20 October 2014
I visited Lenox on a girls leaf peeping trip in mid-October. We found this house to be cozy & warm. It is very quaint & centrally located. It was nice to have most of the comforts...
See all reviews
From
€240
Per Night
View Details
1 / 12
Payment Protection
Austerlitz
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
Details Reviews (3) Make Enquiry
From
€160
Per Night
View Details
1 / 16
Payment Protection
Stockbridge, MA
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (4) Make Enquiry
4 of 5 stars Reviewed 24 October 2013
Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
5 of 5 stars Reviewed 30 September 2013
We rented this cabin originally for 5: 2 adults and 3 children (6,11,13). At the last minute our older daughter (18) decided to join us. The cabin is very spacious and...
See all reviews
From
€156
Per Night
View Details
1 / 10
Payment Protection
Great Barrington, MA
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (9) Make Enquiry
5 of 5 stars Reviewed 17 August 2014
We stayed at the cottage for three days, and it was just as lovely as advertised. The space is perfect for a couple, with a comfortable queen bed and well-equipped kitchen...
5 of 5 stars Reviewed 22 July 2014
My wife and I were extremely lucky to find Efrem and Frederica's cottage in The Berkshires. We really enjoyed the beautiful and relaxing view that their backyard had to offer! The...
See all reviews
From
€120
Per Night
View Details
1 / 16
Payment Protection
Stephentown
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 29 October 2014
Beautiful home, comfortable BUT there were no sheets on the bed. And when I contacted the owner nothing was done about it. Kitchen was outfitted with everything. There was a...
4 of 5 stars Reviewed 28 July 2014
We had a great time and would recommend this house to anyone looking for a quiet escape. The house was in great condition, with full kitchen, lots of room, carpeting, amazing...
See all reviews
From
€260
Per Night
View Details
1 / 27
Payment Protection
Great Barrington, MA
5 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
Details Reviews (1) Make Enquiry
3 of 5 stars Reviewed 11 September 2014
This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
See all reviews
From
€160
Per Night
View Details
1 / 11
Payment Protection
Stockbridge, MA
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
3 of 5 stars Reviewed 31 July 2014
Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus...
See all reviews
From
€140
Per Night
View Details
1 / 4
Payment Protection
South Lee, MA
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
From
€80
Per Night
View Details
1 / 12
Payment Protection
South Lee, MA
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Make Enquiry
From
€601
Per Night
View Details
1 / 13
Payment Protection
Stephentown
4 Bedrooms, 4 Bathrooms, Sleeps 16
Details Make Enquiry
From
€601
Per Night
View Details
1 / 7
Payment Protection
Lee, MA
5 Bedrooms, 5 Bathrooms, Sleeps 12
Details Make Enquiry
From
€180
Per Night
View Details
1 / 11
Payment Protection
Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Make Enquiry
From
€220
Per Night
View Details
1 / 21
Payment Protection
Lee, MA
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
From
€3,606
Per Week
View Details
1 / 25
Payment Protection
Great Barrington, MA
6 Bedrooms, 6 Bathrooms, Sleeps 12
Details Make Enquiry
From
€120
Per Night
View Details
1 / 15
Payment Protection
Dalton, MA
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
From
€240
Per Night
View Details
1 / 13
Payment Protection
Chatham
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
From
€104
Per Night
View Details
1 / 20
Payment Protection
Pittsfield, MA
3 Bedrooms, 1 Bathroom, Sleeps 8
Booking
Details Make Enquiry
From
€194
Per Night
View Details
1 / 15
Payment Protection
Lenox, MA
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
From
€401
Per Night
View Details
1 / 11
Payment Protection
Stockbridge, MA
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
From
€160
Per Night
View Details
1 / 12
Payment Protection
Lee, MA
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Go to map view
Book Online(70)
Use filters to find the best results!

Suitability

  • Wheelchair access (11)
  • Elder access (35)
  • Suitable for children (54)
  • Pet friendly (24)
  • Smoking allowed (0)

Amenities

  • Internet (68)
  • Other outdoor space (66)
  • Grill (58)
  • Washer/Dryer (56)
  • Parking (55)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities