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North Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for North Canaan vacation rentals

Property grounds

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥39,377
￥82,805 total
includes taxes & fees
Sep 7 - Sep 8
Cheerful 3-bedroom cottage with woodstove
Coffee/tea maker, fridge, microwave, oven

2. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥43,016
￥65,133 total
includes taxes & fees
Sep 16 - Sep 17
Home in Great Barrington
Interior

3. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is ￥30,470
￥47,917 total
includes taxes & fees
Sep 16 - Sep 17
Cozy Riverside Berkshires Retreat
TV, fireplace, printers

4. 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, (7 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 ￥90,248
￥211,568 total
includes taxes & fees
Aug 19 - Aug 20
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 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 ￥51,413
￥89,481 total
includes taxes & fees
Sep 1 - Sep 2
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Coffee/tea maker, fridge, microwave, oven

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is ￥16,490
￥24,647 total
includes taxes & fees
Sep 15 - Sep 16
Cozy 1-bedroom studio in serene Great Barrington with AC
Terrace/patio

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, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is ￥20,087
￥38,404 total
includes taxes & fees
Aug 31 - Sep 1
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Smart TV, books

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

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is ￥90,869
￥141,769 total
includes taxes & fees
Aug 19 - Aug 20
Fantastic 2-bedroom house with AC in quaint Hillsdale.
Coffee/tea maker, fridge, microwave, oven

9. Renovated Downtown Great Barrington House

Renovated Downtown Great Barrington House
Great Barrington
8.0 out of 10, Very Good, (2 reviews)
"This is a very nice place to stay. My wife and I both remarked on how comfortable we felt there. A proper home away from home. It was well stocked on all fronts, including the kitchen. And I think what put the finishing touch on was the attention to detail... The towels were large, the bathroom rolls were Charmin Ultrasoft, and there were tissue boxes everywhere you're likely to need them. The hosts seem to work with a service, so you can reach someone with questions immediately, and the hosts...
United States
Anonymous traveler
The price is ￥172,907
￥277,589 total
includes taxes & fees
Aug 23 - Aug 24
Renovated Downtown Great Barrington House
Beach nearby, sun loungers, beach towels

10. 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, (3 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 ￥31,960
￥50,650 total
includes taxes & fees
Sep 16 - Sep 17
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Coffee/tea maker, fridge, microwave, oven

11. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is ￥141,884
￥234,810 total
includes taxes & fees
Aug 19 - Aug 20
A Country Lodge Straight Out of the Pages of a Great Novel
Dining

12. 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 ￥37,304
￥83,056 total
includes taxes & fees
Aug 19 - Aug 20
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
TV

13. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is ￥45,275
￥92,511 total
includes taxes & fees
Sep 16 - Sep 17
Treetop Hideaway in Tyringham
Desk, iron/ironing board, WiFi, bed sheets

14. 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 ￥23,898
￥30,335 total
includes taxes & fees
Aug 19 - Aug 20
The Brooks Motel: Exceptional Suite
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is ￥27,899
￥50,752 total
includes taxes & fees
Sep 1 - Sep 2
Sweet Cozy Victorian in Housatonic. Close to everything.
Outdoor dining

16. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is ￥64,167
￥101,301 total
includes taxes & fees
Aug 30 - Aug 31
Stockbridge In-town Escape
4 bedrooms, travel crib, WiFi, bed sheets

17. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is ￥81,065
￥139,164 total
includes taxes & fees
Sep 2 - Sep 3
Stylish Mid-century Modern Berkshires Cape
2 bedrooms, WiFi (free), bed sheets

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is ￥19,800
￥35,922 total
includes taxes & fees
Aug 30 - Aug 31
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

19. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is ￥47,667
￥59,993 total
includes taxes & fees
Sep 6 - Sep 7
rural, serene + sophisticated space
Smart TV, fireplace

20. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 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 ￥26,304
￥45,434 total
includes taxes & fees
Sep 2 - Sep 3
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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Top North Canaan Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"It is a little pricey for what you get but we loved the property and the area and will be back!"
Patricia 2-night trip
Posted 1 hour ago
The Red Lion Inn

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:

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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 vacation rentals in North Canaan?

Yes, we have vacation rentals near popular sights in North Canaan, or you can choose a more secluded option if you'd like a relaxing place to stay.

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

Cozy Riverside Berkshires Retreat: You might want to consider this vacation home rental near North Canaan, which is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in North Canaan?

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

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, Campbell Falls State Park and Land of Nod Vineyard and Winery are other places worth a visit.

What are vacation rentals like in North Canaan?

Vacation rentals are privately owned accommodations you can stay in for a few days or a quick weekend in North Canaan. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family gatherings.