Canaan Vacation Rentals

Name: Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Price range: $552 total

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Vacation Rentals in Canaan

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont MA

Located in Egremont, this vacation home is in a rural location, within a 10-minute drive of W.E.B. Du Bois Boyhood Homesite and Mount Everett State Reservation.

Kitchen

Washer

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington MA

With a stay at this vacation home, you'll be centrally located in Great Barrington, within a 10-minute drive of Monument Mountain and Housatonic River.

Hot Tub

Kitchen

Home in Great Barrington

Great Barrington MA

$247 nightly

$275 total

Mar 15 - Mar 16

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Great Barrington, just a 3-minute walk from Housatonic River and 10 minutes by foot from Mahaiwe Performing Arts Center.

Kitchen

Washer

Family Ski Getaway in the Berkshires

Great Barrington MA

$284 nightly

$317 total

Mar 10 - Mar 11

Total with taxes and fees

Located in Great Barrington, this vacation home is on a river, a short 4-minute walk from Monument Mountain Reservation and within 1 minutes by car from Housatonic River.

Kitchen

Washer

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA

With a stay at this vacation home in Lanesborough, you'll be within a 10-minute drive of Crane Museum of Papermaking and Barrington Stage Company.

Hot Tub

Kitchen

Amore Estate - beautiful room with many places to explore and relax in.

Lenox MA

With a stay at this vacation home in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Wyndhurst Golf & Club.

Pool

Kitchen

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington MA

Located in Great Barrington, this vacation home is within a 5-minute drive of Ski Butternut and Lake Buel.

Kitchen

Washer

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

Coxsackie NY

When you stay at this vacation home in Athens, you'll be on the beach, just steps from Hudson River and Hudson River Islands State Park.

Pool

Hot Tub

Lake house with a game room

Athens NY

Located in Coxsackie, this vacation home is on a lake, a 1-minute drive from Sleepy Hollow Lake and 8 minutes from Hudson River Islands State Park.

Pool

Kitchen

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Great Barrington MA

Located in Great Barrington, this vacation home is in a rural location, within a 5-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Pool

Kitchen

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield MA

Located in Pittsfield, this vacation home is on a lake, within a 5-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.

Hot Tub

Kitchen

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

Stockbridge MA

$494 nightly

$552 total

Mar 11 - Mar 12

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Stockbridge, within a 15-minute drive of Tanglewood Music Center and Housatonic River.

Kitchen

Washer

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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.