Canaan Vacation Rentals from CA $229: Short-Term Rentals for 2026

Q: What's the top vacation rental in Canaan?

Cozy Riverside Berkshires Retreat : This vacation home rental outside of Canaan 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.

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Our top choices for 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

Great Barrington

bob i.

CA $229 total

includes taxes & fees

Sep 7 - Sep 8

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

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

winsted

CA $329 total

includes taxes & fees

Sep 1 - Sep 2

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

3. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

CA $719 total

includes taxes & fees

Sep 22 - Sep 23

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

4. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

CA $277 total

includes taxes & fees

Aug 31 - Sep 1

A loft bedroom with a television, wooden shelves, a ladder, and a skylight.

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

Winchester

CA $309 total

includes taxes & fees

Sep 1 - Sep 2

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

6. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

CA $496 total

includes taxes & fees

Aug 31 - Sep 1

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

7. Home in Great Barrington

Great Barrington

HEATHER G.

CA $562 total

includes taxes & fees

Sep 3 - Sep 4

8. Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington

Louisa A.

CA $568 total

includes taxes & fees

Aug 31 - Sep 1

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Top Canaan Hotel Reviews

Little Cat Lodge

10/10 Excellent

"Beautifully decorated and comfortable with great continental breastfast and stunning mountain views."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

The Little Lion

8/10 Good

"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."

The Abner Hotel

10/10 Excellent

"I think this hotel would be wonderful in any season...beautiful area to walk on the wide, stately streets with beautiful 1800's home in the summer, spring or fall; lots of beautiful autumn leaves in the fall, perfect New England town with center green in winter, summer, spring and fall, to beautiful spring with flowers all over the town too. At Abner Hotel you can enjoy any season with the great rooftop bar, the cozy fireplace in the lounge outside the restaurant in the winter.... A special attraction for attorneys or anyone interested in the law is the unique nature of this property which was a renovated and preserved old courthouse.... Don't forget the fascinating attraction of country's very first Law School, walking distance from the hotel! Lourdes of Litchfield Grotto, lovely with outdoor masses, stations of the cross, gift shop and Cafe, open to all, just down the road."

Find out more about Canaan

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Canaan. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Canaan?

Yes, there are vacation rentals close to the most popular local attractions in Canaan, or you can select a more secluded option if you're looking for a relaxing stay. Canaan is known for its restaurants and coffeehouses.

What's the top vacation rental in Canaan?

Cozy Riverside Berkshires Retreat: This vacation home rental outside of Canaan 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 Canaan?

Expedia has 5 vacation rentals for your stay in Canaan.

What’s there to see and do in Canaan?

Housatonic River and Edith Scoville Memorial Sanctuary are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Campbell Falls State Park and Lawrence Field.

What’s a vacation rental in Canaan like?

Vacation rentals are private properties you can stay in for a long or short time in Canaan. Vacation rentals offer amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for families.

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Check prices for these dates

Our top choices for Canaan vacation 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.

3. Cheerful 3-bedroom cottage with woodstove

4. The Brooks Motel: Exceptional Suite

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

6. Cozy Attic 10 min to Llitchfield

7. Home in Great Barrington

8. Cozy Modern Farmhouse Private Apt - 3 Beds

9. Cozy Riverside Berkshires Retreat

10. Art House 3 Beds Close to Warner Theater

11. Pristine Cozy Walkable Downtown 2BR Getaway

12. Mid Century Modern Studio w/ Full Kitchen - Newly Built

13. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

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

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

16. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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

18. stylish Berkshires Retreat

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

20. The Brooks Motel: Exceptional Suite

Find vacation rentals that suit your style

Top Canaan Hotel Reviews

Little Cat Lodge

Quality Inn Great Barrington

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Red Lion Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Litchfield Inn

The Little Lion

The Abner Hotel

Find out more about Canaan

Frequently asked questions

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