Holiday Rentals North Canaan from £125: Find Short-Term Rentals & Holiday Accommodations

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

The Meadows House @ Otis Ridge w/ 7-person hot tub : This holiday home rental outside of North Canaan is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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In two weeks

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Our top choices for North Canaan holiday rentals

Coffee/tea maker, fridge, microwave, oven

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

Great Barrington

Shelly B.

includes taxes & fees

12 Sept - 13 Sept

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

winsted

Steve

3. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

22 Sept - 23 Sept

4. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

includes taxes & fees

9 Sept - 10 Sept

Desk, iron/ironing board, WiFi, bed sheets

5. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

includes taxes & fees

7 Sept - 8 Sept

6. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

8 Sept - 9 Sept

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

Winchester

includes taxes & fees

8 Sept - 9 Sept

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

Hillsdale

Kenny

includes taxes & fees

7 Sept - 8 Sept

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Top North Canaan Hotel Reviews

The Red Lion Inn

10/10 Excellent

"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

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 £125 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?

The Meadows House @ Otis Ridge w/ 7-person hot tub: This holiday home rental outside of North Canaan is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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, Campbell Falls State Park and Edith Scoville Memorial Sanctuary 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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Our top choices for North Canaan holiday rentals

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

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