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North Canaan Vacation Rentals

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Check prices for these dates

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

Our top choices for North Canaan vacation 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, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is CA $249
CA $605 total
includes taxes & fees
Nov 2 - Nov 3
Cheerful 3-bedroom cottage with woodstove
A living room with a fireplace, bookshelves, a television, and a comfortable seating area.

2. 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 CA $281
CA $636 total
includes taxes & fees
Oct 25 - Oct 26
Sharon Retreat w/ Private Yard
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

3. 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 CA $304
CA $478 total
includes taxes & fees
Nov 3 - Nov 4
Home in Great Barrington
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

4. 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, (9 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 CA $139
CA $210 total
includes taxes & fees
Oct 28 - Oct 29
Cozy 1-bedroom studio in serene Great Barrington with AC
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

5. 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 CA $538
CA $912 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is CA $562
CA $976 total
includes taxes & fees
Nov 16 - Nov 17
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A residential garden with a stone border, various plants, and a house in the background.

7. 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, (6 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 CA $280
CA $463 total
includes taxes & fees
Nov 16 - Nov 17
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
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 CA $145
CA $279 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful and cozy 1 bed 1 bath in quaint Winchester
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.

9. 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, (9 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 CA $795
CA $1,855 total
includes taxes & fees
Oct 28 - Oct 29
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

10. 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 CA $211
CA $267 total
includes taxes & fees
Oct 28 - Oct 29
The Brooks Motel: Exceptional Suite
A staircase with a wooden handrail and a white wall with a light switch.

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 CA $247
CA $396 total
includes taxes & fees
Oct 28 - Oct 29
Leaf-Peeper Paradise in the Berkshires
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

12. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is CA $345
CA $815 total
includes taxes & fees
Oct 23 - Oct 24
Cozy Cottage-Sunset On The Lake
A dining area with a wooden table, black chairs, and a vase with green plants.

13. 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)
"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 CA $281
CA $494 total
includes taxes & fees
Oct 28 - Oct 29
Sweet Cozy Victorian in Housatonic. Close to everything.
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

14. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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 CA $377
CA $795 total
includes taxes & fees
Nov 16 - Nov 17
Treetop Hideaway in Tyringham
A compact RV interior with a kitchenette, a sofa with patterned upholstery, and a window with a view.

15. 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 CA $202
CA $257 total
includes taxes & fees
Oct 29 - Oct 30
Cozy Camper tucked into the woods
A modern kitchen with white cabinets, a large island, and a skylight.

16. 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)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is CA $1,250
CA $2,069 total
includes taxes & fees
Oct 28 - Oct 29
A Country Lodge Straight Out of the Pages of a Great Novel
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 CA $337
CA $838 total
includes taxes & fees
Oct 25 - Oct 26
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A two-story house with a front porch, a small balcony, and a white picket fence.

18. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is CA $198
CA $602 total
includes taxes & fees
Oct 28 - Oct 29
Cozy Modern Farmhouse Private Apt - 3 Beds
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

19. 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 CA $212
CA $633 total
includes taxes & fees
Oct 25 - Oct 26
Art House 3 Beds Close to Warner Theater
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

20. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (8 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is CA $222
CA $280 total
includes taxes & fees
Oct 28 - Oct 29
The Brooks Motel: Exceptional Suite
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

Blackberry River Inn

Blackberry River Inn

10/10 Excellent
"Beautiful place! Comfortable atmosphere and relaxing quiet time."
Ruth 1-night trip
Posted 2 hours ago
Blackberry River Inn

Find out more about North Canaan

Everything you need to know about North Canaan vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the North Canaan vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect North Canaan vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

North Canaan vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in North Canaan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A North Canaan vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of North Canaan vacation rentals we have selected for you start as low as CA $210 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on North Canaan rentals

At Expedia, we put the best North Canaan vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top North Canaan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream North Canaan vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around North Canaan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: You might want to consider this vacation home rental near North Canaan, which offers a fireplace, a garden, and a barbecue grill 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 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, Edith Scoville Memorial Sanctuary and Connecticut Railroad Historical Museum 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.