A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.

Holiday Homes in Canaan

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Canaan holiday homes

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

1. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AU$301
includes taxes & fees
27 Oct - 28 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

2. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is AU$317
includes taxes & fees
5 Nov - 6 Nov
1800s Carriage house in Berkshires / Hudson Valley
A white two-story house with a porch, surrounded by trees and a hill.

3. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AU$614
includes taxes & fees
27 Oct - 28 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A cozy living room with a sofa, a fireplace, and large windows.

4. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is AU$977
includes taxes & fees
27 Oct - 28 Oct
Luxury Barn Near Hudson With New Private Sauna
A camping setup with a metal chair and a table by a river in a forest.

5. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is AU$480
includes taxes & fees
27 Oct - 28 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.2 out of 10, Wonderful, (10 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is AU$839
includes taxes & fees
27 Oct - 28 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

7. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is AU$959
includes taxes & fees
2 Nov - 3 Nov
Ellie’s Overlook, best view in the Berkshires!
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

8. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is AU$801
includes taxes & fees
27 Oct - 28 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

9. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is AU$908
includes taxes & fees
1 Nov - 2 Nov
Secluded Family Home in Serene Stockbridge Woods
Pool

10. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is AU$758
includes taxes & fees
27 Oct - 28 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A dining area with a wooden table, chairs, and a ceiling fan.

11. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is AU$395
includes taxes & fees
27 Oct - 28 Oct
Leaf-Peeper Paradise in the Berkshires
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

12. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is AU$488
includes taxes & fees
27 Oct - 28 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A wooden deck with a staircase leading to a covered porch area.

13. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is AU$204
includes taxes & fees
1 Nov - 2 Nov
All the comforts of home
A cozy living room with a fireplace, red and striped furniture, and large windows offering a view of greenery.

14. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Richmond
The price is AU$1,785
includes taxes & fees
27 Oct - 28 Oct
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
A modern living room with a sofa, armchair, coffee table, and TV.

15. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
The price is AU$835
includes taxes & fees
1 Nov - 2 Nov
Spacious Central Berkshires Home for Groups
A living room with a sofa, armchairs, a coffee table, and a television.

16. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is AU$884
includes taxes & fees
27 Oct - 28 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A wooden deck with a table and chairs, surrounded by a white railing.

17. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is AU$689
includes taxes & fees
27 Oct - 28 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

18. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AU$1,621
includes taxes & fees
27 Oct - 28 Oct
Hancock Village Inn Near Jiminy Peak
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

19. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AU$497
includes taxes & fees
27 Oct - 28 Oct
Home in Great Barrington
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Canaan Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Excellent accommodations! Our room was very clean and comfortable. We appreciated the well lit parking lot, quality breakfast foods, and friendly staff. Thank you!"
Nancy 2-night trip
Posted less than an hour ago
Comfort Inn & Suites East Greenbush - Albany

Find out more about Canaan

Canaan Holiday Homes information

Number of reviews
206
Accommodation
433 Holiday Homes
Lowest Price
AU$204
Highest Price
AU$1,785