Vacation rentals in North Canaan

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Top-rated vacation rentals in North Canaan

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Sep 14 – 21

ﺩ.ﺇ393 per night
Guest favorite

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 100 reviews

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Nov 17 – 24

ﺩ.ﺇ1,012 per night
Guest favorite

Apartment in Canaan

4.98 out of 5 average rating, 102 reviews

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Apr 28 – May 5

ﺩ.ﺇ482 per night

Popular amenities for North Canaan vacation rentals

Stay near North Canaan's top sights

Stateline Pizza4 locals recommend
Stop and Shop Plaza24 locals recommend
Roma Pizzeria4 locals recommend
Beckley Iron Furnace State Park8 locals recommend
Collin's Diner3 locals recommend
Great Falls Brewing Company16 locals recommend

Other great vacation rentals in North Canaan

Guest favorite

Home in Colebrook

4.99 out of 5 average rating, 200 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Dec 16 – 23

ﺩ.ﺇ842 per night
Guest favorite

Apartment in Winchester

4.91 out of 5 average rating, 338 reviews

Gateway to the Berkshires

Mar 15 – 22

ﺩ.ﺇ360 per night
Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 340 reviews

Lakeside Private Guest Suite

Mar 5 – 12

ﺩ.ﺇ347 per night
Guest favorite

Home in Monterey

4.92 out of 5 average rating, 306 reviews

Charming cottage w/ gorgeous views.

Feb 26 – Mar 5

ﺩ.ﺇ616 per night
Guest favorite

Cottage in Goshen

4.98 out of 5 average rating, 102 reviews

Country Cottage in Goshen

Apr 2 – 9

ﺩ.ﺇ503 per night
Guest favorite

Guesthouse in Granby

4.99 out of 5 average rating, 699 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

Feb 28 – Mar 7

ﺩ.ﺇ594 per night
Guest favorite

Cabin in Canaan

4.95 out of 5 average rating, 63 reviews

Dog Friendly Log Cabin of Your Dreams!

Dec 6 – 13

ﺩ.ﺇ996 per night
Superhost

Apartment in Winsted

4.85 out of 5 average rating, 60 reviews

Haven at Highland lake

Jan 12 – 19

ﺩ.ﺇ215 per night
Guest favorite

Guesthouse in Sharon

5.0 out of 5 average rating, 59 reviews

Cottage with a Waterfall View

Aug 19 – 26

ﺩ.ﺇ400 per night
Guest favorite

Apartment in Amenia

5.0 out of 5 average rating, 18 reviews

Amenia Main St Cozy Studio

Sep 11 – 18

ﺩ.ﺇ282 per night
Guest favorite

Home in Salisbury

5.0 out of 5 average rating, 20 reviews

Greystone at Twin Lakes

Jun 17 – 24

ﺩ.ﺇ640 per night
Superhost

Home in Sheffield

4.82 out of 5 average rating, 65 reviews

Charming Berkshires Cottage by Evergreen Home

Apr 4 – 11

ﺩ.ﺇ659 per night

Destinations to explore