North Canaan Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for North Canaan holiday rentals

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,391
HK$3,210 total
includes taxes & fees
18 Nov - 19 Nov
Cheerful 3-bedroom cottage with woodstove
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

2. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is HK$600
HK$906 total
includes taxes & fees
13 Nov - 14 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

3. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
The price is HK$1,692
HK$3,633 total
includes taxes & fees
9 Nov - 10 Nov
Sharon Retreat w/ Private Yard
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

4. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is HK$1,695
HK$2,532 total
includes taxes & fees
10 Nov - 11 Nov
Home in Great Barrington
A sandy beach with a lake and forest in the background.

5. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is HK$1,404
HK$2,270 total
includes taxes & fees
18 Nov - 19 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

6. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is HK$2,702
HK$4,516 total
includes taxes & fees
10 Nov - 11 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

7. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (55 reviews)
"It was a nice stay…worked well for the event we attended in town. The host was very nice to work with"
United States
Roberta S.
The price is HK$925
HK$1,714 total
includes taxes & fees
1 Dec - 2 Dec
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A wooden cabin interior with a bench, a rug, and a hanging plant.

8. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is HK$811
HK$1,478 total
includes taxes & fees
16 Nov - 17 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

9. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is HK$3,136
HK$5,004 total
includes taxes & fees
21 Nov - 22 Nov
Fantastic 2-bedroom house with AC in quaint Hillsdale.
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

10. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$3,136
HK$5,227 total
includes taxes & fees
17 Nov - 18 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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 HK$1,587
HK$2,360 total
includes taxes & fees
9 Nov - 10 Nov
Leaf-Peeper Paradise in the Berkshires
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

12. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,387
HK$1,633 total
includes taxes & fees
6 Dec - 7 Dec
The Brooks Motel: Exceptional Suite
A cozy living room with a sofa, armchair, wooden coffee table, and a dining area with a table and chairs.

13. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (80 reviews)
"We very much enjoyed our two week stay in July. The cabin suited our needs in every regard. Our lab was also able to fully relax, whether it was napping on the screen porch or sitting by the fire pit. For those looking to explore the region, the location could not be better situated. Hoping to return over Christmas."
United States
Richard M.
The price is HK$1,372
HK$2,695 total
includes taxes & fees
8 Nov - 9 Nov
Ideal location for summer and winter activities with plenty of outdoor space.
A wooden fence, a potted plant, a wooden bench, and a small garden area with a stone pathway.

14. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is HK$1,129
HK$1,366 total
includes taxes & fees
7 Nov - 8 Nov
Cozy Camper tucked into the woods
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

15. 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 HK$1,318
HK$2,313 total
includes taxes & fees
8 Nov - 9 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

16. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (10 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,459
HK$9,919 total
includes taxes & fees
15 Nov - 16 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

17. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is HK$1,878
HK$4,450 total
includes taxes & fees
8 Nov - 9 Nov
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

18. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is HK$1,185
HK$3,271 total
includes taxes & fees
8 Nov - 9 Nov
Art House 3 Beds Close to Warner Theater
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

19. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is HK$1,288
HK$2,111 total
includes taxes & fees
8 Nov - 9 Nov
Pristine Cozy Walkable Downtown 2BR Getaway
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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Find out more about North Canaan

Search for holiday rentals in North Canaan on Expedia! You can easily find your home rentals, villas, holiday apartments in North Canaan using one of the methods below:

  • View our selection of featured holiday rentals in North Canaan
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Look no further and take a look at our great range of rental properties in North Canaan!

Frequently Asked Questions

Can I find holiday rentals in North Canaan?

Yes, there are holiday rentals close to the most popular sights in North Canaan, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that North Canaan has to offer?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This holiday home rental outside of North Canaan offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in North Canaan?

Choose from 8 Expedia holiday rentals in North Canaan for a memorable holiday.

What can I see and do in North Canaan?

Housatonic River and Lawrence Field are a couple of lovely local spots to get outside and enjoy nature. While here, Edith Scoville Memorial Sanctuary and Connecticut Railroad Historical Museum are other places worth a visit.

What are holiday rentals like in North Canaan?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in North Canaan. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips or small group gatherings.