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.

Guest favorite

Home in Canaan

5.0 out of 5 average rating, 132 reviews

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.

Dec 27 – Jan 3

$135 per night
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 13 – 20

$88 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.

Jun 18 – 25

$115 per night

Popular amenities for Canaan vacation 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 vacation rentals in Canaan

Guest favorite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 179 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Jul 18 – 25

$136 per night
Guest favorite

Bungalow in Hillsdale

4.86 out of 5 average rating, 129 reviews

Copake Lake & Catamount/Berkshires Cottage

Apr 8 – 15

$93 per night
Guest favorite

Vacation home in Torrington

4.97 out of 5 average rating, 128 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Mar 1 – 8

$146 per night
Guest favorite

Home in Colebrook

4.99 out of 5 average rating, 200 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Feb 25 – Mar 4

$198 per night
Guest favorite

Cottage in Great Barrington

4.91 out of 5 average rating, 223 reviews

Cottage on Scenic Road

Nov 5 – 12

$117 per night
Guest favorite

Cottage in Sharon

4.9 out of 5 average rating, 120 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

Nov 30 – Dec 7

$177 per night
Guest favorite

Cottage in Great Barrington

4.98 out of 5 average rating, 124 reviews

Newly built cottage on working farm

Nov 8 – 15

$100 per night
Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 12 reviews

Private rooms and full bath in a Historic Home

Mar 18 – 25

$126 per night
Guest favorite

Guesthouse in Sharon

5.0 out of 5 average rating, 59 reviews

Cottage with a Waterfall View

Aug 19 – 26

$94 per night
Guest favorite

Apartment in Amenia

5.0 out of 5 average rating, 18 reviews

Amenia Main St Cozy Studio

Aug 7 – 14

$67 per night
Guest favorite

Cabin in Canaan

4.95 out of 5 average rating, 63 reviews

Dog Friendly Log Cabin of Your Dreams!

Jul 19 – 26

$235 per night
Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 81 reviews

Mountain View Getaway

Nov 24 – Dec 1

$91 per night

Destinations to explore

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