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North Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for North Canaan vacation rentals

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

1. 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 ￥17,784
￥26,045 total
includes taxes & fees
Oct 25 - Oct 26
Cozy 1-bedroom studio in serene Great Barrington with AC
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

2. 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 ￥28,031
￥67,515 total
includes taxes & fees
Nov 9 - Nov 10
Cheerful 3-bedroom cottage with woodstove
A wooden cabin interior with a bench, a rug, and a hanging plant.

3. 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 ￥18,182
￥33,320 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful and cozy 1 bed 1 bath in quaint Winchester
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, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ￥36,426
￥56,581 total
includes taxes & fees
Oct 26 - Oct 27
Home in Great Barrington
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 ￥57,371
￥96,450 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A sandy beach with a lake and forest in the background.

6. 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 ￥31,462
￥50,154 total
includes taxes & fees
Nov 16 - Nov 17
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

7. 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 ￥23,715
￥30,102 total
includes taxes & fees
Oct 18 - Oct 19
The Brooks Motel: Exceptional Suite
A staircase with a wooden handrail and a white wall with a light switch.

8. 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 ￥27,747
￥44,591 total
includes taxes & fees
Oct 26 - Oct 27
Leaf-Peeper Paradise in the Berkshires
A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

9. 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 ￥25,043
￥31,505 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Camper tucked into the woods
A two-story house with a front porch, a small balcony, and a white picket fence.

10. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is ￥14,774
￥55,779 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Attic 10 min to Llitchfield
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

11. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ￥11,698
￥50,323 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
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
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 ￥24,980
￥31,696 total
includes taxes & fees
Oct 18 - Oct 19
The Brooks Motel: Exceptional Suite
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

13. 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 ￥42,371
￥88,569 total
includes taxes & fees
Nov 16 - Nov 17
Treetop Hideaway in Tyringham
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is ￥63,240
￥111,079 total
includes taxes & fees
Oct 19 - Oct 20
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A two-story house with a front porch, a small balcony, and a white picket fence.

15. 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 ￥22,076
￥67,017 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Modern Farmhouse Private Apt - 3 Beds
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

16. 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 ￥31,620
￥55,452 total
includes taxes & fees
Oct 18 - Oct 19
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

17. 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 ￥22,624
￥67,259 total
includes taxes & fees
Nov 9 - Nov 10
Art House 3 Beds Close to Warner Theater
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

18. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥23,051
￥59,302 total
includes taxes & fees
Oct 28 - Oct 29
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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)
"It was great!"
United States
Amanda T.
The price is ￥30,830
￥50,513 total
includes taxes & fees
Nov 9 - Nov 10
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 Abner Hotel

The Abner Hotel

10/10 Excellent
"This converted courthouse is very charming, with 12-foot ceilings (I think), hard wood floors, a cool rooftop bar, a great location in the middle of Litchfield's shopping and restaurant district, ample parking in the rear, and a very friendly staff. The breakfast - by Stephanie - was fantastic, with her homemade muffins, overnight oats/chia, fresh fruit, frittatas, and other items. We had the most delicious sea bass for dinner at the Courtroom restaurant on site. Our room was among the smallest, but the king-sized bed was luxurious, the bathroom was very chic, with white and black tiling, and the ceilings were so high that it made it feel bigger. The only drawback was no TV, but we were fine using our laptops for streaming. I'm not sure if TVs are in other rooms. We would definitely stay again."
Robert 1-night trip
Posted 1 hour ago
The Abner Hotel

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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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.