East Canaan Holiday Rentals

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Holiday Rentals in East Canaan

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"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

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

8.8 out of 10, Excellent, (20)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (4)
"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "
The price is AU$207
includes taxes & fees
1 Sept - 2 Sept
Deluxe Queen Room with 2 Queen Beds

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

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

9.4 out of 10, Exceptional, (81)
"Amazing cabin, thank you for a beautiful stay! We came in for a wedding and this was a great location to where the wedding was held. "
Summer Lake Cottage, private beach, Berkshire Hills, small village

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

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....

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

9.4 out of 10, Exceptional, (63)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

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!

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

10.0 out of 10, Exceptional, (5)
"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

Lakefront Summer Spectacular in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (76)
"Great place! Loved waking up to a water view. Very peaceful."
Lakefront Summer Spectacular in New England Just 2 Hours From NYC

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

9.6 out of 10, Exceptional, (44)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA

10.0 out of 10, Exceptional, (1)
"The cabin is charming, rustic, and a perfect getaway for a birthday or romantic weekend trip.The pollinator garden is truly a delight, and I loved watching them in the morning. The garden has even motivated my partner and I to start one at home.I wish that the mosquitoes were not present as well, but they are to be expected during the summer in MA.Overall, the stay was amazing. Marci was super sweet and left some nice gifts for my birthday. I definitely want to have another stay here again!"
Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."
Exclusive Estate, Heated Yearround Outdoor Pool

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (75)
"It's a really lovely home on a beautiful property, with all the amenities we could have possibly needed, and also perfectly peaceful. The host was so welcoming and responsive, which made it that much nicer, too. My only regret is that we couldn't stay longer, and I would definitely want to stay there again. "
Stay Lakeside This Summer!

Renovated Lakefront House w/ Dock: Pets Welcome!

9.0 out of 10, Wonderful, (20)
"the lake house is terrific and having the boats and a fire pit was such a nice thing."
Renovated Lakefront House w/ Dock: Pets Welcome!

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

10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay here. Location was excellent. Very peaceful and quiet. The house was clean and had everything you needed. Would come again!"
The price is AU$607
includes taxes & fees
3 Sept - 4 Sept
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (13)
"We loved staying here! Great location!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (3)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (40)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
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

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 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.