Litchfield, Connecticut

Vacation Rentals in Litchfield, Connecticut

Discover 24 vacation rental properties in Litchfield. From 1 to 5 bedrooms. Average $418/night. 100% have pools.

24 verified listings Book securely on VRBO Prices updated March 2026

24 properties available

Litchfield Hills Hideaway

Litchfield Hills Hideaway

1 bed 1 bath
PoolA/CWiFiBalcony
$151/night
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Charming 1870 cape cottage in Litchfield

Charming 1870 cape cottage in Litchfield

3 beds 1 bath
PoolA/CWiFiBalcony
$250/night
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Cozy Litchfield House w/ Fenced-In Yard & Fire Pit

Cozy Litchfield House w/ Fenced-In Yard & Fire Pit

3 beds 2 baths
PoolA/CWiFiBalcony
$306/night
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Cozy in the hills of Cape Litchfield

Cozy in the hills of Cape Litchfield

2 beds 1 bath
PoolA/CWiFiBalcony
$354/night
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County Seat Colonial

County Seat Colonial

2 beds 1 bath
PoolA/CWiFiBalcony
$357/night
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Historic Colonial...Close to Village Green

Historic Colonial...Close to Village Green

3 beds 2 baths
PoolA/CWiFiBalcony
$425/night
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The Doctor's 1781 House on the Litchfield Green

The Doctor's 1781 House on the Litchfield Green

4 beds 2 baths
PoolA/CWiFiBalcony
$276/night
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Fantastic Cape in Historic Litchfield

Fantastic Cape in Historic Litchfield

2 beds 1 bath
PoolA/CWiFiBalcony
$217/night
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Enjoy colonial charm in one of Litchfield's oldest neighborhoods!

Enjoy colonial charm in one of Litchfield's oldest neighborhoods!

1 bed 1 bath
PoolA/CWiFiBalcony
$171/night
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Expansive Countryside House, 7 Serene Acres with Pond & Woods

Expansive Countryside House, 7 Serene Acres with Pond & Woods

3 beds 2 baths
PoolA/CWiFiBalcony
$338/night
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Private home with stunning sunrise and sunset views.

Private home with stunning sunrise and sunset views.

3 beds 3 baths
PoolA/CWiFiBalcony
$325/night
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Stunning Litchfield home 1 1/2 hours from NYC in idyllic setting, 3 bedrooms

Stunning Litchfield home 1 1/2 hours from NYC in idyllic setting, 3 bedrooms

3 beds 2 baths
PoolA/CWiFiBalcony
$517/night
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Historic Litchfield Luxury Farmhouse

Historic Litchfield Luxury Farmhouse

3 beds 2 baths
PoolA/CWiFiBalcony
$1,275/night
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Cozy remodeled cottage. Close to town, vineyards, restaurants, and farms.

Cozy remodeled cottage. Close to town, vineyards, restaurants, and farms.

1 bed 1 bath
PoolA/CWiFiBalcony
$286/night
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Hilltop House

Hilltop House

3 beds 2 baths
PoolA/CWiFiBalcony
$526/night
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Litchfield hilltop home with long view and sunsets

Litchfield hilltop home with long view and sunsets

4 beds 2 baths
PoolA/CWiFiBalcony
$230/night
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Litchfield Modern Farmhouse

Litchfield Modern Farmhouse

2 beds 2 baths
PoolA/CWiFiBalcony
$297/night
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Historic Litchfield Hills Saltbox on Large Estate!

Historic Litchfield Hills Saltbox on Large Estate!

2 beds 2 baths
PoolA/CWiFiBalcony
$428/night
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Private wooded family retreat with pool along picturesque river

Private wooded family retreat with pool along picturesque river

5 beds 4 baths
PoolA/CWiFiBalcony
$1,398/night
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Tranquil Litchfield Connecticut Retreat".

Tranquil Litchfield Connecticut Retreat".

2 beds 1 bath
PoolA/CWiFiBalcony
$194/night
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Sweetbrier Farm -- Gorgeous Views, Beautiful Home

Sweetbrier Farm -- Gorgeous Views, Beautiful Home

5 beds 3 baths
PoolA/CWiFiBalcony
$507/night
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1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9

1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9

5 beds 4 baths
PoolA/CWiFiBalcony
$349/night
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Litchfield - Hot Tub - Mohawk Mountain - Fireplace

Litchfield - Hot Tub - Mohawk Mountain - Fireplace

2 beds 1 bath
PoolA/CWiFiBalcony
$116/night
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Spectacular Silo House on Litchfield Hills Estate

Spectacular Silo House on Litchfield Hills Estate

2 beds 1 bath
PoolA/CWiFiBalcony
$748/night
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