Holiday Homes in Canaan

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Canaan holiday homes

Smart TV, books

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is NZ$664
includes taxes & fees
30 Mar - 31 Mar
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is NZ$504
includes taxes & fees
30 Mar - 31 Mar
Home in Great Barrington
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"My family and I had a wonderful stay at Nicole’s A-Frame. The cabin was cozy and inviting, and our kids especially loved the loft. The welcome snacks were such a thoughtful touch! We'd love to return! "
United States
Loralee C.
The price is NZ$629
includes taxes & fees
1 Apr - 2 Apr
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is NZ$674
includes taxes & fees
31 Mar - 1 Apr
Litchfield Retreat, Wineries, Foliage & Skiing
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$533
includes taxes & fees
1 Apr - 2 Apr
Cozy Riverside Berkshires Retreat
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
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.
The price is NZ$1,183
includes taxes & fees
29 Mar - 30 Mar
CT Gate House Goshen CT, Gate House Goshen CT
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$846
includes taxes & fees
29 Mar - 30 Mar
Cheerful 3-bedroom cottage with woodstove
Property grounds

3-Bedroom Cabin Getaway With Rustic Charm

3-Bedroom Cabin Getaway With Rustic Charm
Cornwall
8.4 out of 10, Very good, (6 reviews)
"Absolutely beautiful cottage exactly as pictured inside and out. "
United States
Michaela C.
The price is NZ$1,047
includes taxes & fees
2 Apr - 3 Apr
3-Bedroom Cabin Getaway With Rustic Charm
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is NZ$938
includes taxes & fees
1 Apr - 2 Apr
Treetop Hideaway in Tyringham
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (35 reviews)
"A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!"
United States
Susan
The price is NZ$1,213
includes taxes & fees
2 Apr - 3 Apr
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Interior

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is NZ$654
includes taxes & fees
29 Mar - 30 Mar
rural, serene + sophisticated space
TV, fireplace, printers

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, (4 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
The price is NZ$2,179
includes taxes & fees
27 Mar - 28 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is NZ$1,153
includes taxes & fees
2 Apr - 3 Apr
Spacious 5-bedroom house in charming Lee with WiFi
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
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.
The price is NZ$993
includes taxes & fees
6 Apr - 7 Apr
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is NZ$1,474
includes taxes & fees
31 Mar - 1 Apr
Whispering Estate Guest House - A Romantic Countryside Getaway
Fridge, microwave, oven, stovetop

A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is NZ$2,457
includes taxes & fees
31 Mar - 1 Apr
A Country Lodge Straight Out of the Pages of a Great Novel
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

the Alander

the Alander

6/10 Okay
"Great coffee "
John 2-night trip
Posted 23 hours ago
the Alander

Find out more about Canaan

Canaan Holiday Homes information

Number of reviews
189
Accommodation
366 Holiday Homes
Lowest Price
NZ$504
Highest Price
NZ$2,457