Holiday Homes in Canaan

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Canaan holiday homes

Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is €123
includes taxes & fees
5 Feb - 6 Feb
All the comforts of home
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is €318
includes taxes & fees
25 Feb - 26 Feb
Near Tanglewood: Historic Summer Retreat
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3 reviews)
"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 €229
includes taxes & fees
3 Feb - 4 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is €236
includes taxes & fees
23 Feb - 24 Feb
Home in Great Barrington
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is €317
includes taxes & fees
4 Feb - 5 Feb
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
The price is €221
includes taxes & fees
5 Feb - 6 Feb
Hudson Hot Tub & Pet Escape
Fridge, microwave, stovetop, dishwasher

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
8.0 out of 10, Very good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is €461
includes taxes & fees
5 Feb - 6 Feb
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Terrace/patio

Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is €378
includes taxes & fees
3 Feb - 4 Feb
Treat yourself at the stunning June Farms Wellness Huts!
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is €380
includes taxes & fees
8 Feb - 9 Feb
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (9 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is €252
includes taxes & fees
3 Feb - 4 Feb
Family Ski Getaway in the Berkshires
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is €434
includes taxes & fees
5 Feb - 6 Feb
Artists’ Hideaway in Old Chatham
Property grounds

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
The price is €265
includes taxes & fees
3 Feb - 4 Feb
Renovated house. Built in 1890s. No neighbors in sight.
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is €272
includes taxes & fees
16 Feb - 17 Feb
3-bedroom house in beautiful Berkshires, close to amenities!
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, (3 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 €1,118
includes taxes & fees
5 Feb - 6 Feb
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is €540
includes taxes & fees
4 Feb - 5 Feb
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Smart TV, DVD player, books, stereo

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is €438
includes taxes & fees
1 Mar - 2 Mar
Great Barrington Get Away
TV

1 mile to Warren St.- Charming House in Hudson, NY

1 mile to Warren St.- Charming House in Hudson, NY
Hudson
The price is €484
includes taxes & fees
3 Feb - 4 Feb
1 mile to Warren St.- Charming House in Hudson, NY
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 €745
includes taxes & fees
9 Feb - 10 Feb
Spacious 5-bedroom house in charming Lee with WiFi
Property grounds

The Lakeshore House

The Lakeshore House
Niverville
10.0 out of 10, Exceptional, (1 review)
"Excellent stay!"
United States
KEITARO A.
The price is €674
includes taxes & fees
5 Feb - 6 Feb
The Lakeshore House
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 €492
includes taxes & fees
9 Feb - 10 Feb
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Room was clean and nicely equipped with kitchen. Will return if the future. "
William 2-night trip
Posted 22 hours ago
Berkshire Mountain Lodge

Find out more about Canaan

Canaan Holiday Homes information

Number of reviews
176
Accommodation
440 Holiday Homes
Lowest Price
€123
Highest Price
€1,187