East Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for East Canaan vacation rentals

Exterior

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
$295 nightly
The price is $337
Jan 25 - Jan 26
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Exterior

Apartment in Torrington

Cozy Modern Farmhouse Private Apt - 3 Beds
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
$341 nightly
The price is $392
Jan 25 - Jan 26
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Exterior detail

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$627 nightly
The price is $643
Jan 25 - Jan 26
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Dining

Apartment in Torrington

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
$339 nightly
The price is $390
Jan 25 - Jan 26
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
2 bedrooms, desk, free WiFi, bed sheets

Apartment in Torrington

Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (16 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
$211 nightly
The price is $239
Feb 2 - Feb 3
Total with taxes and fees
Charming apartment 7 minute walk to downtown
Smart TV, books

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$339 nightly
The price is $379
Jan 25 - Jan 26
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Interior

Vacation Home in Goshen

Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
$778 nightly
The price is $882
Jan 25 - Jan 26
Total with taxes and fees
Whispering Estate Guest House - A Romantic Countryside Getaway
Interior

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
$613 nightly
The price is $685
Jan 26 - Jan 27
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Fridge, microwave, oven, stovetop

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
$224 nightly
The price is $250
Jan 26 - Jan 27
Total with taxes and fees
Home in Great Barrington
Exterior

Vacation Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
$444 nightly
The price is $504
Jan 25 - Jan 26
Total with taxes and fees
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Interior

Vacation Home in Housatonic

Sweet Cozy Victorian in Housatonic. Close to everything.
10.0 out of 10, Exceptional, (3 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
$240 nightly
The price is $268
Feb 1 - Feb 2
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$179 nightly
The price is $200
Jan 25 - Jan 26
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Exterior

Vacation Home in Stockbridge

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
$582 nightly
The price is $650
Jan 26 - Jan 27
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
TV, fireplace, printers

Vacation Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (3 reviews)
"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
$1,193 nightly
The price is $1,332
Jan 25 - Jan 26
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

Vacation Home in Great Barrington

Family Ski Getaway in the Berkshires
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
$253 nightly
The price is $283
Jan 26 - Jan 27
Total with taxes and fees
Family Ski Getaway in the Berkshires
Smart TV, DVD player, books, stereo

Vacation Home in Great Barrington

Great Barrington Get Away
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
$494 nightly
The price is $552
Jan 25 - Jan 26
Total with taxes and fees
Great Barrington Get Away
3 bedrooms, iron/ironing board, WiFi, bed sheets

Vacation Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
$593 nightly
The price is $662
Feb 8 - Feb 9
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Smart TV, fireplace

Apartment in Great Barrington

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
1 bedroom, desk, iron/ironing board, WiFi

Apartment in Torrington

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
$341 nightly
The price is $392
Jan 25 - Jan 26
Total with taxes and fees
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
$179 nightly
The price is $200
Jan 25 - Jan 26
Total with taxes and fees
The Brooks Motel: Exceptional Suite
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great property, very accommodating. "
Shanice 1-night trip
Posted 4 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about East Canaan

Everything you need to know about East Canaan vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the East Canaan vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

East Canaan vacation 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 low season months. For more hustle and bustle, you may prefer to visit East Canaan in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $250 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on East Canaan rentals

At Expedia, we put the best East Canaan vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in East Canaan?

Yes, you can find vacation rentals near well known sights in East Canaan, or you can select a more remote option if you're looking for relaxation. East Canaan is known for its wineries.

What are some of the best vacation rentals that East Canaan has to offer?

Family Ski Getaway in the Berkshires: You might want to consider this vacation home rental near East Canaan, which 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 as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in East Canaan?

Expedia has 3 vacation 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 larger area, you’ll find Land of Nod Vineyard and Winery and Haystack Mountain State Park.

What’s a vacation rental in East Canaan like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in East Canaan. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a family trip.