East Canaan Holiday Rentals from €146: Search Short-Term Rentals

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

Cozy Riverside Berkshires Retreat : This holiday home rental outside of East 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 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.

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Our top choices for East Canaan holiday rentals

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

winsted

Steve

includes taxes & fees

3 Sept - 4 Sept

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

Great Barrington

bob i.

includes taxes & fees

7 Sept - 8 Sept

3. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

22 Sept - 23 Sept

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

Winchester

includes taxes & fees

13 Sept - 14 Sept

5. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

3 Sept - 4 Sept

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

Great Barrington

Kristin O.

includes taxes & fees

14 Sept - 15 Sept

7. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

includes taxes & fees

8 Sept - 9 Sept

8. Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington

Louisa A.

includes taxes & fees

1 Sept - 2 Sept

9. Pristine Cozy Walkable Downtown 2BR Getaway

Torrington

James M.

includes taxes & fees

16 Sept - 17 Sept

10. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

includes taxes & fees

29 Sept - 30 Sept

11. Art House 3 Beds Close to Warner Theater

Torrington

Brittany M.

includes taxes & fees

1 Sept - 2 Sept

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

Great Barrington

Mary R.

includes taxes & fees

8 Sept - 9 Sept

13. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Torrington

Jaimie S.

includes taxes & fees

3 Sept - 4 Sept

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

Housatonic

Peter S.

includes taxes & fees

1 Sept - 2 Sept

15. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Otis

includes taxes & fees

7 Sept - 8 Sept

16. 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

21 Sept - 22 Sept

17. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

includes taxes & fees

1 Sept - 2 Sept

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

Sherwood Forest

Frank M.

includes taxes & fees

7 Sept - 8 Sept

19. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Hillsdale

includes taxes & fees

1 Sept - 2 Sept

20. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Rebecca K.

includes taxes & fees

1 Sept - 2 Sept

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Top East Canaan Hotel Reviews

Quality Inn Lee - Lenox South

10/10 Excellent

"The hotel was very clean and well maintained. The lobby and stairs were very clean and looked as though everything was painted recently. The room was very clean and modern and bed was comfortable. The bathroom was also clean. We only stayed the one night for a concert at Tanglewood so we didn’t use any of the amenities or have the free breakfast. But if they were anything like the rest of the hotel, I’m sure they were above average. Would definitely stay again when in the area."

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!"

Find out more about East Canaan

Everything you need to know about East 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 East 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 East Canaan holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

East Canaan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in East 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 East 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 East Canaan holiday rentals we have selected for you start as low as €146 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on East Canaan rentals

At Expedia, we put the best East 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 East 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 East 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 East 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 East Canaan?

Yes, there are holiday rentals close to the most popular sights in East Canaan, or you can select a more secluded option if you're looking for a relaxing stay. East Canaan is known for its wineries.

What are some of the best holiday rentals that East Canaan has to offer?

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

Expedia has 3 holiday rentals for your stay in East Canaan.

What’s there to see and do in East Canaan?

While exploring the area, visit family-friendly sights like KidsPlay Museum, or get outside and enjoy nature at Beckley Furnace Industrial Park. In the wider area, you’ll find Land of Nod Vineyard and Winery and Campbell Falls State Park.

What’s a holiday rental in East Canaan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in East Canaan. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips.

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Check prices for these dates

Our top choices for East Canaan holiday rentals

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

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

3. Cheerful 3-bedroom cottage with woodstove