Rent a cabin in Canaan, CT

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Canaan, CT

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Popular cabins

Pennybrook Cottage

Falls Village, CT

8 guests

From 
$500
/hr
5 hr min

Modern House with a View

Sharon, CT

5.0 (2)

40 guests

From 
$250
/hr
4 hr min

Historic Country Farmhouse on 13 Acres

Goshen, CT

14 guests

From 
$400
/hr
2 hr min

1740 Litchfield Luxury Farmhouse

Litchfield, CT

5.0 (1)

12 guests

From 
$599
/hr
2 hr min

Contemporary home secluded in nature with views for as far as the eyes can see

Millerton, NY

5.0 (4)

8 guests

From 
$275
/hr
5 hr min

Cozy Country House with 360 Nature Views

great barrington, MA

12 guests

From 
$200
/hr
4 hr min

Upstate NY Lakehouse with Incredible Sunset Views

Copake, Craryville, NY

10 guests

From 
$400
/hr
1 hr min

Litchfield Estate: 1800s House, Cottage, Red Barn on a Pond

Litchfield, CT

50 guests

From 
$400
/hr
4 hr min

Contemporary Cabin in the Woods

Wassaic, NY

12 guests

From 
$200
/hr
4 hr min

1825 Litchfield Colonial with Manicured Grounds

Litchfield, CT

20 guests

From 
$350
/hr
4 hr min

Modern Scandinavian Farmhouse with Vintage Camper

Gallatin, Ancram, NY

30 guests

From 
$225
/hr
3 hr min

Pine cabin in Berkshire Mountains on 6 acres of woods with pond.

Otis, MA

30 guests

From 
$99
/hr
6 hr min

Home in Morris for Production

Morris, CT

15 guests

From 
$375
/hr
4 hr min

Active farm with pasture views in the Berkshire hills

Great Barrington, HOUSATONIC, MA

25 guests

From 
$100
/hr
5 hr min

Upstate Horse Farm with Functioning Stables, Barn, and 1832 Farmhouse

Stanfordville, NY

50 guests

From 
$400
/hr
5 hr min

Historic country farmhouse with running brook and stonewalls.

Washington, Millbrook, NY

20 guests

From 
$800
/hr
5 hr min

Chic Cottage with Vintage Fireplace & Natual Light

Gallatin, Ancram, NY

20 guests

From 
$150
/hr
4 hr min

Beautiful Remote Home | 5307

Hillsdale, NY

30 guests

From 
$525
/hr
8 hr min

Beautiful Modern Home | 5253

Hillsdale, NY

30 guests

From 
$445
/hr
8 hr min

Stunning, Unique, Modern Location Filled with Light | 5321

Crayville, NY

50 guests

From 
$1,200
/hr
8 hr min

Gorgeous Historic Country Home and Gardens

Claverack, NY

15 guests

From 
$200
/hr
4 hr min

Barns, country setting, pond and Turn of the century larg home

Stanford, Stanfordville, NY

100 guests

From 
$300
/hr
3 hr min

Rural Lakehouse w Mid-century Modern Styling

Sherwood Forest, BECKET, MA

10 guests

From 
$65
/hr
2 hr min

Similar searches in Canaan, CT

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Nearby locations

Amenia, NY
Goshen, CT
Great Barrington, MA
Stanfordville, NY
Hillsdale, NY
Millbrook, NY
Craryville, NY
Red Hook, NY
Hollowville, NY
Salt Point, NY
Becket, MA
Hyde Park, NY
Updated October 25, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.