Canaan Vacation Rentals

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Nov 13 - Nov 14
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Nov 14 - Nov 15
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Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Canaan

Fridge, microwave, oven, stovetop
Charming apartment 7 minute walk to downtown

Charming apartment 7 minute walk to downtown

Torrington
10.0 out of 10, Exceptional, (15)
"We had an amazing stay. The property was very clean and welcoming. Personal touches made us feel at home. A great location close to walking path and downtown. Would highly recommend! "
United States
jennifer b.
$218 nightly
The price is $247
Nov 16 - Nov 17
Total with taxes and fees
Charming apartment 7 minute walk to downtown
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Torrington
9.6 out of 10, Exceptional, (4)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
$230 nightly
The price is $274
Nov 16 - Nov 17
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
Goshen
9.8 out of 10, Exceptional, (7)
"Wonderful stay. It really is a gate house. The property is beautiful and the house is spacious. If I was eloquent,I could go on and on... "
United States
Wilford
$703 nightly
The price is $730
Nov 14 - Nov 15
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Exterior
Cozy Modern Farmhouse Private 2 Bdrm Apartment

Cozy Modern Farmhouse Private 2 Bdrm Apartment

Torrington
10.0 out of 10, Exceptional, (4)
"We were happy to have a clean and comfortable place to stay while in Torrington visiting family. The hotels in town are nasty so this was a great alternative. There is a park across the street and an Office warehouse on the street behind, so it’s quiet at night which was a plus. Inside is definitely as advertised, cozy but not cramped, the furniture and decor is well appointed. We will definitely stay again."
United States
Kelly Grace G.
$264 nightly
The price is $315
Dec 1 - Dec 2
Total with taxes and fees
Cozy Modern Farmhouse Private 2 Bdrm Apartment
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"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.
$217 nightly
The price is $242
Nov 17 - Nov 18
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Fridge, microwave, oven, stovetop
Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Kent
9.8 out of 10, Exceptional, (7)
"The mid-century studio is even cuter than in the photos! Perfect location with walk to town and the wonderful restaurants there. Perfect for a couple. (I highly recommend the almond croissant at Wilsons.) The place is spotlessly clean and easy/quick communications with our host. The snack basket was perfect and the extra water bottles in the fridge saved us on a hike. We will definitely be back, maybe to paddle the nearby Housatonic. :) "
United States
Cathleen B.
$254 nightly
The price is $288
Nov 14 - Nov 15
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"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.
$351 nightly
The price is $392
Nov 16 - Nov 17
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"Nicole was phenomenal, the most speedy and responsive host I've had on any platform. The A-Frame was a perfect, cozy, and quaint little spot for our weekend getaway. It was clean and honestly portrayed in the photos. No complaints whatsoever. Thank you, Nicole!"
United States
James F.
$338 nightly
The price is $377
Nov 17 - Nov 18
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
$253 nightly
The price is $283
Nov 14 - Nov 15
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

Hillsdale
9.2 out of 10, Wonderful, (5)
"The motel was well equipped, clean, and comfortable. It was especially suited for my travel with my dog."
United States
Susan S.
$179 nightly
The price is $200
Nov 14 - Nov 15
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."
United States
Farida K.
$244 nightly
The price is $272
Dec 1 - Dec 2
Total with taxes and fees
Home in Great Barrington
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield
10.0 out of 10, Exceptional, (9)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
United States
Robert B.
$640 nightly
The price is $715
Nov 16 - Nov 17
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (40)
"we had a wonderful time staying at the house, very comfortable and well equipped and responsive host."
United States
lisa s.
$404 nightly
The price is $451
Nov 16 - Nov 17
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Interior
rural, serene + sophisticated space

rural, serene + sophisticated space

Red Hook
10.0 out of 10, Exceptional, (7)
"A beautifully curated barn overlooking a picturesque landscape. Gregg, the owner, really cares and wants to make sure you have everything you need. We stayed over a weekend when we were attending a wedding in the area. It was so nice to have a place to relax amidst all the festivities. The birdsong and bullfrog chorus led us to some of the soundest sleep we’ve enjoyed in a long time. "
United States
Kathryn
$301 nightly
The price is $337
Nov 18 - Nov 19
Total with taxes and fees
rural, serene + sophisticated space
Exterior
Bungalow in the Berkshires

Bungalow in the Berkshires

Lee
10.0 out of 10, Exceptional, (4)
"Great location, very clean and well appointed with everyth"
United States
Nick R.
$345 nightly
The price is $385
Nov 30 - Dec 1
Total with taxes and fees
Bungalow in the Berkshires
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
$466 nightly
The price is $521
Nov 16 - Nov 17
Total with taxes and fees
Great Barrington Get Away
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington
10.0 out of 10, Exceptional, (1)
"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
Nov 14 - Nov 15
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
$661 nightly
The price is $738
Nov 20 - Nov 21
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington
$513 nightly
The price is $573
Nov 19 - Nov 20
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Exterior
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Torrington
$237 nightly
The price is $288
Dec 1 - Dec 2
Total with taxes and fees
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
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 Canaan Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Early check in."
Colleen 1-night trip
Posted 4 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Canaan

Everything you need to know about 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 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 Canaan vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Canaan vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in 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 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 $283 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 Canaan rentals

At Expedia, we put the best 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 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 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 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

Are there vacation rentals in Canaan?

Yes, there are vacation rentals close to the most popular local attractions in Canaan, or you can select a more secluded option if you're looking for a relaxing stay. Canaan is known for its restaurants and coffeehouses.

What's the top vacation rental in Canaan?

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!: This vacation home rental outside of Canaan offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a fridge, a stovetop, and a coffee maker, so you can cook with friends or family. You can relax into your vacation with a garden and foosball.

How many vacation rentals are there in Canaan?

Expedia has 5 vacation rentals for your stay in Canaan.

What’s there to see and do in Canaan?

Housatonic River and Edith Scoville Memorial Sanctuary are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Campbell Falls State Park and North Canaan Town Hall.

What’s a vacation rental in Canaan like?

Vacation rentals are private properties you can stay in for a long or short time in Canaan. Vacation rentals offer amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for families.