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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Canaan vacation rentals

Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.6 out of 10, Exceptional, (4)
"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.
The price is ￥13,895
￥53,323 total
includes taxes & fees
Dec 30 - Dec 31
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is ￥23,605
￥40,143 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Home in Great Barrington
Property grounds
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Apartment in winsted

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.2 out of 10, Wonderful, (46)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is ￥13,910
￥26,301 total
includes taxes & fees
Dec 28 - Dec 29
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ￥13,817
￥96,917 total
includes taxes & fees
Jan 4 - Jan 5, 2026
CT Gate House Goshen CT, Gate House Goshen CT
Exterior
Cozy Modern Farmhouse Private Apt - 3 Beds

Apartment in Torrington

Cozy Modern Farmhouse Private Apt - 3 Beds
10.0 out of 10, Exceptional, (4)
"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.
The price is ￥17,798
￥59,443 total
includes taxes & fees
Dec 30 - Dec 31
Cozy Modern Farmhouse Private Apt - 3 Beds
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,762
￥58,384 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Charming apartment 7 minute walk to downtown

Apartment in Torrington

Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (16)
"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.
The price is ￥24,823
￥43,690 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Charming apartment 7 minute walk to downtown
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
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 ￥25,010
￥61,244 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"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.
The price is ￥61,355
￥105,329 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Guesthouse Cabin vacation rentals in Berkshire County
Fridge, microwave, oven, stovetop
Mid Century Modern Studio w/ Full Kitchen - Newly Built

Apartment in Kent

Mid Century Modern Studio w/ Full Kitchen - Newly Built
9.8 out of 10, Exceptional, (10)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥30,443
￥38,913 total
includes taxes & fees
Dec 29 - Dec 30
Mid Century Modern Studio w/ Full Kitchen - Newly Built
TV, offices
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥24,823
￥31,299 total
includes taxes & fees
Dec 28 - Dec 29
The Brooks Motel: Exceptional Suite
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥37,000
￥78,298 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cheerful 3-bedroom cottage with woodstove
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Vacation Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
2.0 star property
The price is ￥41,372
￥82,822 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Game room
Family Ski Getaway in the Berkshires

Vacation Home in Great Barrington

Family Ski Getaway in the Berkshires
9.4 out of 10, Exceptional, (6)
The price is ￥31,614
￥46,474 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Family Ski Getaway in the Berkshires
Exterior detail
Whispering Estate Guest House - A Romantic Countryside Getaway

Vacation Home in Goshen

Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (5)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is ￥124,896
￥187,890 total
includes taxes & fees
Dec 25 - Dec 26
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Vacation Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (3)
"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 ￥88,801
￥208,008 total
includes taxes & fees
Dec 25 - Dec 26
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Fridge, microwave, oven, stovetop
Catamount, Zip Line, Private Setting, Book Now!

Vacation Home in Egremont

Catamount, Zip Line, Private Setting, Book Now!
10.0 out of 10, Exceptional, (7)
"This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."
United States
Jason W.
The price is ￥101,985
￥217,228 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Catamount, Zip Line, Private Setting, Book Now!
Outdoor dining
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Vacation Home in Hillsdale

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
10.0 out of 10, Exceptional, (1)
"Beautiful house! It was a big house and we loved all the rooms and how they were decorated! When we first arrived the heat wasn’t working and the host had someone there with the half hour fixing the problem. Beautiful quite area as well "
United States
Gabrielle T.
The price is ￥60,887
￥175,204 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Fridge, microwave, oven, stovetop
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Vacation Home in Monterey

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
10.0 out of 10, Exceptional, (1)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
The price is ￥132,390
￥276,796 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Vacation Home in Lee

Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very Good, (2)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is ￥81,807
￥142,823 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Spacious 5-bedroom house in charming Lee with WiFi
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Canaan Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
Cooper 1-night trip
Posted 4 days ago
Quality Inn

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?

Peace and quiet on the lake: This vacation home rental outside of Canaan is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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 Eddy Field 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 Edith Scoville Memorial Sanctuary.

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.