East Canaan Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in East Canaan

Peace and quiet on the lake

9.6 out of 10, Exceptional, (208)
"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! "
Peace and quiet on the lake

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (210)
"The cabin is quiet, tidy, and comfortable. It is within driving distance of several hiking trails and was a great place to spend a long weekend. The host was friendly and communicative, and made sure that we had everything we needed for a nice stay. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (5)
"I booked the weekend for my girlfriends birthday with a couple of her friends. The game room was a massive hit as was the propane fireplace outside. We also enjoyed watching the snow fall on the frozen lake. William was very responsive to messages and calls. We enjoyed our stay immensely and are hoping to come back in the summer"
Berkshires Lakefront Retreat

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (37)
"The house was great. Plenty of bedrooms to fit our party of 16 (mix of kids and adults). Very comfortable hang out spaces and places to play games. The barn with the basketball court was awesome also! We got a lot of use out of that. The house was clean and everything worked well except that the dishwasher was broken. That was unfortunate, but these things happen, and we made due. The owner said that it would be fixed in a week or so, so hopefully not an issue for anyone else. Owner was...
Beautiful Berkshire Farm House on 160+ Acres

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (16)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
The price is AU$4,269
includes taxes & fees
19 Feb - 20 Feb
Private Estate, Heated Yearround Outdoor Pool

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.4 out of 10, Exceptional, (21)
"This house is on the small side but recently remodeled. Had everything we needed for a weekend stay when skiiing Catamount. A short ride to the mountain and to some great restaurants near Great Barrington made it very convenient. The location is a short walk to the lake which would be great for the summer. "
The price is AU$602
includes taxes & fees
16 Feb - 17 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Home in Great Barrington

10.0 out of 10, Exceptional, (18)
"Our family had a wonderful experience and stay. "
The price is AU$506
includes taxes & fees
24 Feb - 25 Feb
Home in Great Barrington

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge

5 Minutes from Catamount Ski Area

9.0 out of 10, Wonderful, (21)
"Cozy spot after skiing. "
5 Minutes from Catamount Ski Area

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (96)
"We had an amazing time. We had several out of town guests who stayed at the home and then a birthday party with local guests in the ballroom. The ballroom is absolutely stunning. The chef enjoyed the kitchen. There was plenty of parking and a beautiful setting. I would stay again. "
A Grand property in Historic Stockbridge

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (85)
"Place is great. Has a old farmhouse feel with an update. Lots of spots within the house for people to hang out. We did a family birthday get together and had a great time. "
Antique Farmhouse Totally Restored

Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.

10.0 out of 10, Exceptional, (20)
"We were a group of 4 long time girlfriends on a Girls' Weekend. This house was perfect for us. The house is set fairly far back from the road which gives you an abundance of privacy. There are 3 bedrooms (king, king, and 2 full beds). If you don't mind sharing a room with one of your besties, then this completely updated home is for you! We selected the home for the hot tub and firepit. We used the hot tub both nights of our weekend stay! We loved the lights in the trees...was so relaxing...
Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (16)
"We enjoyed our stay in this lovely, remote location. The home was welcoming and inviting. The property is large with nice views. It is a bit of a drive to reach stores and restaurants but that is what we like! The upstairs loft is one wide-open space with several beds so you need to be okay with sharing the space. "
Peaceful, Post and Beam Loft, Sleeps 9

Large Barn styled vacation home that fits groups with space to spare.

9.8 out of 10, Exceptional, (57)
"Everything was ideal for our Thanksgiving get together. Setting and views were perfect, made even more so with a timely blanket of fresh snow. An amazing amount of cooking provisions allowed us to cook as if we were in our own kitchen. Lots of options for keeping a large group entertained, and sleeping accomodations that pleased everyone. Host was very helpful with check-in communications and gracious with check in and out times without other bookings adjacent to ours. All in all a very special...
Large Barn styled vacation home that fits groups with space to spare.

Minutes from downtown Great Barrington, Convenient location

10.0 out of 10, Exceptional, (46)
"Our family stayed here for a long weekend to do some skiing. The house was perfectly located a short drive from Catamount. The house was super clean and had everything we needed. Marianne was a lovely host providing us with info before our check in and being available if we needed anything (we were all set but the offer was so nice). My son loved that there were some board games to choose from too! Would definitely recommend this property "
Minutes from downtown Great Barrington, Convenient location

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

10.0 out of 10, Exceptional, (3)
"We had a lovely stay! The space was perfect for our group of 4 moms looking for a peaceful getaway. The host was very responsive. Only note for those visiting, rideshares (Uber and otherwise) are few and far between. Schedule ahead! We'd definitely stay again :)"
Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Peaceful Retreat Compound 10 Minutes to Great Barrington!

10.0 out of 10, Exceptional, (22)
"This home is located in a beautiful area with plenty of nature surrounding. The amenities included are incredible. A large group of us visited and had so much fun on the pickle ball courts, hanging around the bonfire, and relaxing with the sauna and hot tub. This place can’t be beat!!"
Peaceful Retreat Compound 10 Minutes to Great Barrington!

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is AU$1,389
includes taxes & fees
18 Feb - 19 Feb
Guesthouse Cabin vacation rentals in Berkshire County
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.
Don't see what you're looking for?
See all available properties in East Canaan
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in East Canaan you may be interested in

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (375)
"The host Heidi was friendly and fun to talk with at breakfast (I was travelling alone). She knows a lot about the area and history which was nice to hear. The house was quiet and clean and I'd stay here again."
The price is AU$191
includes taxes & fees
15 Feb - 16 Feb
Locust Tree Bed and Breakfast LLC

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

3.5 star property
9.0 out of 10, Wonderful, (595)
"Room was clean and facility was nice"
The price is AU$233
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"The Red Lion Inn is in iconic in in the heart of the berkshires. Very relaxing the staff is so friendly and accommodating very clean and a great area for getting food. Love this place"
The price is AU$329
includes taxes & fees
6 Mar - 7 Mar
The Red Lion Inn
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.

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?

Peace and quiet on the lake: This holiday home rental outside of East Canaan is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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.