East Canaan Holiday Rentals

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Holiday Rentals in East Canaan

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.6 out of 10, Exceptional, (16)
"We came for a concert at Tanglewood. Property was just as photos described, walking distance to downtown Lee restaurants, easy access to highway and other towns. Great spot for multiple family or friends to get together."
United States
Karyn P.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Pet Friendly Riverfront Home in Great Barrington
8.8 out of 10, Excellent, (3)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$448
includes taxes & fees
4 Nov - 5 Nov
Pet Friendly Riverfront Home in Great Barrington
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
8.6 out of 10, Excellent, (26)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
United States
Angela C.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (228)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
United States
Donald G.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Summer Lake Cottage, private beach, Berkshire Hills, small village
9.4 out of 10, Exceptional, (84)
"The house is very comfortable and perfect for visiting with family and friends.We enjoyed the roomy kitchen space. The porch is great for relaxing and gazing at the tranquil lake. We appreciated the use of the canoe and the dock."
United States
Jenny P.
Summer Lake Cottage, private beach, Berkshire Hills, small village
Peace and quiet on the lake
9.6 out of 10, Exceptional, (226)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
The Goshen Glass Chalet
9.6 out of 10, Exceptional, (41)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
United States
Tracy F.
The Goshen Glass Chalet
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is NZ$1,193
includes taxes & fees
30 Oct - 31 Oct
Guesthouse Cabin vacation rentals in Berkshire County
Stay Lakeside This Summer!
9.8 out of 10, Exceptional, (78)
"Beautiful lake views, comfy and cozy house! We had a wonderful time. Thank you for sharing your home with us. "
United States
Anne-Marie A.
Stay Lakeside This Summer!
Private Island - Largest Fresh Water Reservoir in Mass
8.6 out of 10, Excellent, (9)
"We had a great time. The owner Bill was a great host."
United States
Drew D.
Private Island - Largest Fresh Water Reservoir in Mass
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
9.4 out of 10, Exceptional, (69)
"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
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (11)
"Everything was great...and beautiful!"
United States
Nicole L.
The price is NZ$692
includes taxes & fees
29 Oct - 30 Oct
The Blue Elm - A Historic Berkshire Cottage
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
10.0 out of 10, Exceptional, (159)
"The location was beautiful. Directions for parking and access to enter were clear. The house felt more like someone’s personal residence than a vacation rental. There were clothes in the closets, food left in the kitchen and no iron and ironing board. The mattresses sagged so we all rolled to the middle when sleeping. With some furniture updates and better cleaning to address the musty smell, cobwebs and ants, this could be a gem."
United States
Annette
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (1)
"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 NZ$2,450
includes taxes & fees
29 Oct - 30 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
9.4 out of 10, Exceptional, (16)
"A short getaway with family. "
United States
Sunita E.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
10.0 out of 10, Exceptional, (55)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
United States
Emily R.
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Beautiful retreat in a lake community to the enjoy the summer season.
10.0 out of 10, Exceptional, (42)
"very relaxing"
United States
Tom G.
Beautiful retreat in a lake community to the enjoy the summer season.
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$656
includes taxes & fees
29 Oct - 30 Oct
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Stunning Renovated Victorian
10.0 out of 10, Exceptional, (54)
"Really loved the property! Was returning to Great Barrington for a reunion of sorts. The house was a perfect spot to relax and reconnect. The space is very well appointed. The fab kitchen and outdoor / porch areas were perfect for the occasion. Very peaceful and welcoming place. We were a group of ladies in our 40s, but well stocked with things for littles as well. Highly recommended!"
United States
Jessica W.
Stunning Renovated Victorian
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
10.0 out of 10, Exceptional, (11)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
United States
Tyler A.
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
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 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 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 Riverfront Escape in Great Barrington - "Whiskers on the Water": 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.

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 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.