Search Vacation Homes in Canaan

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Our top choices for Canaan vacation homes

Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

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)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$614 nightly
The price is $629
Dec 28 - Dec 29
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$335 nightly
The price is $374
Jan 5 - Jan 6, 2026
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
$230 nightly
The price is $257
Jan 5 - Jan 6, 2026
Total with taxes and fees
Home in Great Barrington
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
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
Jan 5 - Jan 6, 2026
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$450 nightly
The price is $503
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Game room
Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Jan 4 - Jan 5, 2026
Total with taxes and fees
Family Ski Getaway in the Berkshires
Fridge, microwave, oven, stovetop
Modern Ranch Retreat in Hudson Valley

Modern Ranch Retreat in Hudson Valley

Modern Ranch Retreat in Hudson Valley
Millerton
10.0 out of 10, Exceptional, (4)
"Great communication and a fantastic property! The setting is quiet and short walk to downtown Millerton. The Harlem Valley Rail Trail Line is just down the road which offers excellent opportunities for adventures!"
United States
Scott E.
Modern Ranch Retreat in Hudson Valley
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
2.0 star property
Goshen
$450 nightly
The price is $510
Dec 23 - Dec 24
Total with taxes and fees
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Fridge, microwave, oven, stovetop
Great Barrington Get Away

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.
$496 nightly
The price is $554
Jan 4 - Jan 5, 2026
Total with taxes and fees
Great Barrington Get Away
Property grounds
Charming 3-bedroom Modern cottage with lakeside views

Charming 3-bedroom Modern cottage with lakeside views

Charming 3-bedroom Modern cottage with lakeside views
2.0 star property
Hartland
$1,310 nightly
The price is $1,483
Dec 25 - Dec 26
Total with taxes and fees
Charming 3-bedroom Modern cottage with lakeside views
Outdoor dining
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Hillsdale
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.
$1,156 nightly
The price is $1,295
Jan 19 - Jan 20, 2026
Total with taxes and fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
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
$1,189 nightly
The price is $1,328
Dec 25 - Dec 26
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior detail
Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
$1,070 nightly
The price is $1,213
Dec 23 - Dec 24
Total with taxes and fees
Whispering Estate Guest House - A Romantic Countryside Getaway
Fridge, microwave, oven, stovetop
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Monterey
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.
$1,587 nightly
The price is $1,773
Jan 18 - Jan 19, 2026
Total with taxes and fees
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1)
"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.
$526 nightly
The price is $588
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

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, (2)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
$819 nightly
The price is $915
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Interior
rural, serene + sophisticated space

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
$304 nightly
The price is $341
Jan 4 - Jan 5, 2026
Total with taxes and fees
rural, serene + sophisticated space
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

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 2 days ago
Quality Inn

Find out more about Canaan

Canaan Vacation Homes information

Number of reviews
119
Accommodation
365 Vacation Homes
Lowest Price
$257
Highest Price
$1,773

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