Vacation rentals in Canaan

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Top-rated holiday rentals in Canaan

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

Guest favourite
Home in Canaan
Country 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.
6 – 13 Nov
5.0 out of 5 average rating, 131 reviews
Guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.
15 – 22 Feb
4.99 out of 5 average rating, 199 reviews
Guest favourite
Apartment in Copake Falls
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!
29 Aug – 5 Sept
4.93 out of 5 average rating, 247 reviews

Popular amenities for Canaan holiday rentals

Stay near Canaan's top sights

Mountainside Cafe19 locals recommend
Toymakers Cafe5 locals recommend
Falls Village Inn21 locals recommend
Great Falls connecticut7 locals recommend
Music Mountain11 locals recommend
Great Mountain Forest Iron Trail3 locals recommend

Other great holiday rentals in Canaan

Guest favourite
Cottage in Great Barrington
Cottage on Scenic Road
16 – 23 June
4.91 out of 5 average rating, 223 reviews
Guest favourite
Guesthouse in New Marlborough
COZY GUESTHOUSE MINUTES AWAY FROM HIKING!
5 – 12 Aug
4.91 out of 5 average rating, 179 reviews
Guest favourite
Cottage in Goshen
Country Cottage in Goshen
4 – 11 July
4.98 out of 5 average rating, 102 reviews
Guest favourite
Cottage in Sharon
Foxfire Hill: A Bit of Luxury in the Countryside
15 – 22 Sept
4.9 out of 5 average rating, 121 reviews
Guest favourite
Guesthouse in Granby
Windy Top Cottage ~ A Romantic "European" Getaway
14 – 21 Feb
4.99 out of 5 average rating, 696 reviews
Guest favourite
Holiday home in Torrington
Modern/Private Five ★ /Hotel quality stay/1 BR Apt
15 – 22 June
4.97 out of 5 average rating, 128 reviews
Guest favourite
Apartment in Canaan
Private rooms and full bath in a Historic Home
30 Nov – 7 Dec
5.0 out of 5 average rating, 12 reviews
Guest favourite
Guesthouse in Sharon
Cottage with a Waterfall View
3 – 10 May
5.0 out of 5 average rating, 58 reviews
Guest favourite
Cabin in Canaan
Dog Friendly Log Cabin of Your Dreams!
2 – 9 Nov
4.95 out of 5 average rating, 61 reviews
Guest favourite
Apartment in Canaan
Mountain View Getaway
10 – 17 Jan
5.0 out of 5 average rating, 81 reviews
Guest favourite
Apartment in Amenia
Amenia Main St Cozy Studio
30 June – 7 July
5.0 out of 5 average rating, 17 reviews
Guest favourite
Cottage in Canaan
The Cottage at Great Falls Luxury Getaway.
13 – 20 Jan
4.97 out of 5 average rating, 77 reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Litchfield County
  5. Canaan