Canaan Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Rentals in Canaan

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.
The price is ¥20,574
¥38,082 total
includes taxes & fees
Nov 12 - Nov 13
Charming apartment 7 minute walk to downtown

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.
The price is ¥13,654
¥41,968 total
includes taxes & fees
Dec 1 - Dec 2
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

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
The price is ¥18,104
¥99,984 total
includes taxes & fees
Nov 11 - Nov 12
CT Gate House Goshen CT, Gate House Goshen CT

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.
The price is ¥18,564
¥48,671 total
includes taxes & fees
Dec 1 - Dec 2
Cozy Modern Farmhouse Private 2 Bdrm Apartment

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.
The price is ¥20,712
¥37,188 total
includes taxes & fees
Dec 11 - Dec 12
Sweet Cozy Victorian in Housatonic. Close to everything.

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.
The price is ¥34,520
¥44,147 total
includes taxes & fees
Nov 13 - Nov 14
Mid Century Modern Studio w/ Full Kitchen - Newly Built

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.
The price is ¥24,578
¥60,185 total
includes taxes & fees
Nov 11 - Nov 12
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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

Sherwood Forest
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ¥22,369
¥57,889 total
includes taxes & fees
Nov 17 - Nov 18
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

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.
The price is ¥31,068
¥45,671 total
includes taxes & fees
Nov 11 - Nov 12
Pet Friendly Riverfront Home in Great Barrington

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.
The price is ¥24,394
¥30,758 total
includes taxes & fees
Nov 11 - Nov 12
The Brooks Motel: Exceptional Suite

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.
The price is ¥27,616
¥45,071 total
includes taxes & fees
Nov 17 - Nov 18
Home in Great Barrington

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.
The price is ¥59,834
¥105,736 total
includes taxes & fees
Nov 11 - Nov 12
Guesthouse Cabin vacation rentals in Berkshire County

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (40)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ¥30,224
¥69,234 total
includes taxes & fees
Nov 11 - Nov 12
Cheerful 3-bedroom cottage with woodstove

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
The price is ¥33,599
¥52,924 total
includes taxes & fees
Nov 11 - Nov 12
rural, serene + sophisticated space

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.
The price is ¥42,191
¥59,124 total
includes taxes & fees
Nov 30 - Dec 1
Bungalow in the Berkshires

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.
The price is ¥43,725
¥80,202 total
includes taxes & fees
Nov 11 - Nov 12
Great Barrington Get Away

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
The price is ¥86,851
¥203,777 total
includes taxes & fees
Nov 11 - Nov 12
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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.
The price is ¥58,683
¥114,046 total
includes taxes & fees
Nov 16 - Nov 17
Spacious 5-bedroom house in charming Lee with WiFi

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington
The price is ¥52,163
¥88,427 total
includes taxes & fees
Nov 11 - Nov 12
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Torrington
The price is ¥14,728
¥44,036 total
includes taxes & fees
Dec 7 - Dec 8
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Canaan Hotel Reviews

Find out more about Canaan

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

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

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

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.