East Canaan Holiday Rentals

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Holiday Rentals in East Canaan

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (209)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

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

9.4 out of 10, Exceptional, (59)
"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

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (9)
"Enjoyed the foliage and some nice hikes. House was comfortable and clean. Owner was responsive and helpful. We arrived at night and had trouble locating the property when our gps failed. Owner was helpful guiding us to the house. I suggest arriving in the light of day. "
Berkshires Cabin 2 Mi to Appalachian Trail!

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

9.8 out of 10, Exceptional, (37)
"Beautiful property located in the woods with plenty of privacy. 3 floors with a lot of elbow room and a tennis court also! Very good communication with the owners with easy check in/check out instructions. "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

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....

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

Newly renovated cottage on the lake!

10.0 out of 10, Exceptional, (22)
"We love live live this property. It is perfect for what we need. Our daughter lives just a shirt distance away in Torrington. This is our second time staying in this house. We love it"
Newly renovated cottage on the lake!

Private Estate, Heated YEARROUND Outdoor Pool

10.0 out of 10, Exceptional, (13)
"The country setting provided a quiet retreat. The home is well equipped: plenty of beds, multiple gathering places, pool with towels (although it was pretty cold until the pool guy came and provided help). The outdoor grill provides additional cooking space. The home is within easy driving to many places of interest. We had a nice week at this home."
Private Estate, Heated YEARROUND Outdoor Pool

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

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

9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is AU$577
includes taxes & fees
26 Nov - 27 Nov
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Great Barrington Walkable to Lake and Town!

9.6 out of 10, Exceptional, (5)
"Needed a rental in a hurry, lucked into Lucas’ house. Quiet, comfortable and cozy. Great visit. Thank you for hosting me and Birdie. "
Great Barrington Walkable to Lake and Town!

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (25)
"We had a great time staying at Lars place. The hot tub was very relaxing and the location was just what we were looking for to get away for a few days."
The Meadows House @ Otis Ridge w/ 7-person hot tub

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"It was a pleasure to find this gem of a cabin available for a night so we could attend a concert at Tanglewood, despite living out of state. The location was lovely, convenient and quiet; the cabin was impeccably appointed (thanks for the fresh flowers in every room and bottle of Riesling!) and very clean with every possible amenity; and the hosts were communicative, friendly and helpful. Overall, this was an idyllic mix of quaint/cute/unique and function/comfort/ease. I will absolutely seek out...
Perfect Vacation Get Away - Historical New Marlborough

Stockbridge Home, Come Experience The Berkshires!

10.0 out of 10, Exceptional, (24)
"We enjoyed everything about this lovely house in the Berkshires--the latest appliances, thoughtful details (throws on all the beds and sofas), a great backyard. Would highly recommend! "
Stockbridge Home, Come Experience The Berkshires!

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (14)
"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."
Peaceful, Post and Beam Loft, Sleeps 9
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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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, (367)
"It was okay"
The price is AU$186
includes taxes & fees
26 Nov - 27 Nov
Locust Tree Bed and Breakfast LLC

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1020)
"We liked the last century charm and excellent staff. We will definitely return"
The price is AU$317
includes taxes & fees
2 Dec - 3 Dec
The Red Lion Inn

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 star property
9.0 out of 10, Wonderful, (568)
"The unit was perfect in size, very good quality of towels. For the cribs, they provided new sheets and blanket that was important for us. "
The price is AU$243
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Private Estate, Heated YEARROUND Outdoor Pool: This holiday home rental outside of East Canaan offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 7 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 Infinity Music Hall and Bistro.

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.