Vacation rentals in Canaan
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Top-rated vacation rentals in Canaan
Guests agree: these stays are highly rated for location, cleanliness, and more.
Home in Canaan
5.0 out of 5 average rating, 132 reviewsCountry Cottage
Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.
Mar 12 – 19
Apartment in Copake Falls
4.93 out of 5 average rating, 250 reviewsModern 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
Apartment in Canaan
4.98 out of 5 average rating, 102 reviewsWest 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
Vacation rentals for every style
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Popular amenities for Canaan vacation rentals
Other great vacation rentals in Canaan
Apartment in Winchester
4.91 out of 5 average rating, 338 reviewsGateway to the Berkshires
Mar 15 – 22
Guesthouse in New Marlborough
4.91 out of 5 average rating, 179 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Jul 17 – 24
Vacation home in Torrington
4.97 out of 5 average rating, 128 reviewsModern/Private Five ★ /Hotel quality stay/1 BR Apt
Mar 21 – 28
Home in Colebrook
4.99 out of 5 average rating, 200 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Dec 16 – 23
Bungalow in Hillsdale
4.86 out of 5 average rating, 129 reviewsCopake Lake & Catamount/Berkshires Cottage
Apr 26 – May 3
Cottage in Great Barrington
4.91 out of 5 average rating, 223 reviewsCottage on Scenic Road
Mar 23 – 30
Cottage in Great Barrington
4.98 out of 5 average rating, 124 reviewsNewly built cottage on working farm
Nov 7 – 14
Apartment in Canaan
5.0 out of 5 average rating, 12 reviewsPrivate rooms and full bath in a Historic Home
Mar 17 – 24
Guesthouse in Sharon
5.0 out of 5 average rating, 59 reviewsCottage with a Waterfall View
Aug 19 – 26
Apartment in Amenia
5.0 out of 5 average rating, 18 reviewsAmenia Main St Cozy Studio
Sep 11 – 18
Apartment in Winsted
4.85 out of 5 average rating, 60 reviewsHaven at Highland lake
Jan 12 – 19
Apartment in Canaan
5.0 out of 5 average rating, 81 reviewsMountain View Getaway
Nov 17 – 24
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