East Canaan Holiday Rentals

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Our top choices for East Canaan holiday rentals

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (38)
"The apartment has everything you might need for a comfortable stay. Perfect location. The host is very responsive and always ready to help. The place is very clean and beautiful. I highly recommend it and will be happy to come back next year. "
United States
Elena
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington
Great Barrington
9.4 out of 10, Exceptional, (6)
The price is AU$453
includes taxes & fees
15 Dec - 16 Dec
Pet Friendly Riverfront Home in Great Barrington

Peace and quiet on the lake

Peace and quiet on the lake
Sherwood Forest
9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Northwest Harwinton
8.8 out of 10, Excellent, (28)
"Great little place, beutiful view to enjoy your coffee."
United States
Shaun H.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AU$597
includes taxes & fees
15 Dec - 16 Dec
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Great Barrington
10.0 out of 10, Exceptional, (54)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$575
includes taxes & fees
15 Dec - 16 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Egremont
9.8 out of 10, Exceptional, (25)
"Farmhouse was as pictured and very clean. Grounds and location were gorgeous "
United States
kathy l.
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

The Goshen Glass Chalet

The Goshen Glass Chalet
Goshen
9.6 out of 10, Exceptional, (42)
"The place was very nice met all of our expectations. "
United States
Marie G.
The Goshen Glass Chalet

Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Cornwall
9.6 out of 10, Exceptional, (53)
"Great house and great stay!"
United States
Timothy P.
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Remodeled Lakefront retreat!!! Don't forget to book for ski season!

Remodeled Lakefront retreat!!! Don't forget to book for ski season!
Copake
9.8 out of 10, Exceptional, (14)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
United States
Melissa D.
Remodeled Lakefront retreat!!! Don't forget to book for ski season!

A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge
Stockbridge
10.0 out of 10, Exceptional, (104)
"Great house with gracious and responsive hosts. Everything in working order and the houseclean and grand."
United States
David H.
A Grand property in Historic Stockbridge

Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored
Sheffield
9.8 out of 10, Exceptional, (94)
"The property was beautiful. Very spacious, inside and out. "
United States
Michelle C.
Antique Farmhouse Totally Restored

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington
10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage
Sheffield
10.0 out of 10, Exceptional, (15)
"It was wonderful!! The hosts were fantastic and the place was lovely. Highly recommend. "
United States
noel s.
The Blue Elm - A Historic Berkshire Cottage

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Sherwood Forest
9.6 out of 10, Exceptional, (232)
"We appreciated how clean and well stocked the cottage was. The owner was very easy to work with. Accurate description of a quiet, secluded get-away in the woods "
United States
Roberta F.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is AU$789
includes taxes & fees
14 Dec - 15 Dec
Great Barrington Get Away

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Lee
9.4 out of 10, Exceptional, (71)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge
Becket
9.8 out of 10, Exceptional, (17)
"Great weekend away. Thank you!"
United States
Karen P.
Quintessential 6-BR Berkshires Lodge

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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (2)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AU$2,023
includes taxes & fees
12 Dec - 13 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 East Canaan Hotel Reviews

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, 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 favourite 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 depend 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 AU$453 per night. Entering your travel dates in the search wizard might find you 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?

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of East Canaan is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. 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 Harney and Sons Tea Tasting Room, 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 Haystack Mountain 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.