North Canaan Holiday Rentals from €127: Search Short-Term Rentals

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Our top choices for North Canaan holiday rentals

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

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

Great Barrington

Deborah S.

includes taxes & fees

12 Oct - 13 Oct

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

2. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

2 Nov - 3 Nov

A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Winchester

Thomas C.

includes taxes & fees

1 Nov - 2 Nov

A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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

winsted

traci

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

26 Oct - 27 Oct

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

Great Barrington

Marc R.

includes taxes & fees

7 Oct - 8 Oct

A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

7. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

includes taxes & fees

4 Oct - 5 Oct

A compact RV kitchen with a stove, sink, and cabinets, a dining area with a bench, and a window with a view of greenery.

8. Cozy Camper tucked into the woods

Sandisfield

"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...

hannah w.

includes taxes & fees

7 Oct - 8 Oct

A two-story house with a front porch, a small balcony, and a white picket fence.

9. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

includes taxes & fees

2 Nov - 3 Nov

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

11. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

includes taxes & fees

13 Oct - 14 Oct

A wooden cabin with a porch, a grill, and a flower planter.

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

Hillsdale

Kenny

includes taxes & fees

15 Oct - 16 Oct

A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

13. Art House 3 Beds Close to Warner Theater

Torrington

Brittany M.

includes taxes & fees

4 Oct - 5 Oct

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

14. Treetop Hideaway in Tyringham

Monterey

"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!! "

Samantha G.

includes taxes & fees

28 Oct - 29 Oct

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

15. Cozy Cottage-Sunset On The Lake

Otis

Rose Angela M.

includes taxes & fees

23 Oct - 24 Oct

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

16. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Great Barrington

17. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

includes taxes & fees

15 Oct - 16 Oct

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Housatonic

Peter S.

includes taxes & fees

8 Oct - 9 Oct

19. Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington

Louisa A.

includes taxes & fees

4 Oct - 5 Oct

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Great Barrington

Mark M.

includes taxes & fees

19 Oct - 20 Oct

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Top North Canaan Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Steven was very helpful and so nice. He went above and beyond to help me find a lost item."

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

The Abner Hotel

10/10 Excellent

"We loved our stay- the room was so well presented/had everything we could need, and we felt so well looked after by all staff. We enjoyed the breakfast, and drinks on the rooftop bar were definitely a highlight! We had dinner one out of the two nights we were staying, which was also lovely. Highly recommend if you’re in the Litchfield area!"

Find out more about North Canaan

Everything you need to know about North Canaan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the North Canaan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

North Canaan holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of North Canaan holiday rentals we have selected for you start as low as €127 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 holiday 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 holiday.

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 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.

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Check prices for these dates

Our top choices for North Canaan holiday rentals

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

2. Cheerful 3-bedroom cottage with woodstove

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