East Canaan Holiday Rentals

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Check prices for these dates

In two weeks
26 Sept - 28 Sept
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec
In four months
2 Jan - 4 Jan

Holiday Rentals in East Canaan

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (222)
"Very cosy and quiet place. We enjoyed conueing on the lake, we had it to ourselves. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Guesthouse Cabin vacation rentals in Berkshire County
Dining

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. "
The price is HK$2,874
HK$5,411 total
includes taxes & fees
16 Sept - 17 Sept
Guesthouse Cabin vacation rentals in Berkshire County
Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (82)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

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

9.6 out of 10, Exceptional, (30)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Interior

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (80)
"Great place! Loved waking up to a water view. Very peaceful."
Lakefront Fall Foliage in New England Just 2 Hours From NYC
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
The price is HK$1,558
HK$3,210 total
includes taxes & fees
22 Sept - 23 Sept
The Blue Elm - A Historic Berkshire Cottage
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior detail

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (2)
"Great experience overall! Property is beautiful and the guest home is situated nicely with access to the backyard and pond. Everything was very clean and well kept with everything in the home that we needed. The hosts were very kind and welcomed us making the stay enjoyable. Would recommend. "
The price is HK$3,505
HK$5,974 total
includes taxes & fees
16 Sept - 17 Sept
Whispering Estate Guest House - A Romantic Countryside Getaway
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Dining

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

8.8 out of 10, Excellent, (23)
"Very nice had everything you needed !"
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Smart TV, fireplace, DVD player

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

10.0 out of 10, Exceptional, (27)
"Great house. More then Enough room for two families. Clean and as described. Super close to butternut ski mountain. "
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (19)
"My husband and I came here for our 10th anniversary with our 9-year-old. The house itself is so charming and historic and cozy, with tons of space. We loved that there are two different stairways to the second floor, which has two parts not connected to each other. Kitchen and small table and seating area are delightful to spend time in. We had a gorgeous fire in the family room in the evening. Best of all are the grounds, huge and gorgeous, green and serene, with a lovely pond. Communication...
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (10)
"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!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"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!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
The Goshen Glass Chalet
Outdoor dining

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (40)
"we couldn't ask for a better place. It had all the conveniences we like. The host did a great job here."
The Goshen Glass Chalet
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

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

9.4 out of 10, Exceptional, (66)
"Location cannot be outdone. This rental was spacious, well stocked, extremely clean, and a very responsive kind owner. Highly recommended:)"
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Private Island - Largest Fresh Water Reservoir in Mass
Interior

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (220)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is HK$1,262
HK$3,088 total
includes taxes & fees
24 Sept - 25 Sept
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
The Studio mini home away from home in the Berkshires
Outdoor dining

The Studio mini home away from home in the Berkshires

9.6 out of 10, Exceptional, (29)
"Great place to stay in Berkshires."
The Studio mini home away from home in the Berkshires
Luxury Barn Retreat . Year-Round Scenic “Park Like”Paradise.
Fridge, microwave, oven, stovetop

Luxury Barn Retreat . Year-Round Scenic “Park Like”Paradise.

10.0 out of 10, Exceptional, (137)
"Quiet and secluded, but close to everything you may need and plenty of wildlife to observe."
Luxury Barn Retreat . Year-Round Scenic “Park Like”Paradise.
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

the Alander

the Alander

10/10 Excellent
"I was in the area for a wedding so only stayed for a brief overnight. Great communication by the owners. Room was large, charming, and clean. I would definitely stay here again if I was in the area. One thing is to download directions to the hotel and how to get into your room prior to your arrival as cell service in the area is spotty. Once there, it is not a problem as they have excellent WiFi "
Joel 1-night trip
Posted 1 day ago
the Alander

Find out more about East Canaan

Find out more about East Canaan

Search for holiday rentals in East Canaan on Expedia! You can easily find your home rentals, villas, holiday apartments in East Canaan using one of the methods below:

  • View our selection of featured holiday rentals in East Canaan
  • Use the map to find apartments and other holiday homes in the East Canaan neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in East Canaan while they last

Look no further and take a look at our great range of rental properties in East Canaan!

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?

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!: This holiday home rental outside of East Canaan is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books 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 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.