Weston, Connecticut

Vacation Rentals in Weston, Connecticut

Discover 16 vacation rental properties in Weston. From 1 to 6 bedrooms. Average $558/night. 100% have pools.

16 verified listings Book securely on VRBO Prices updated March 2026

16 properties available

Relaxing Upscale Studio w/Kitchen in nature + comfy queen bed

Relaxing Upscale Studio w/Kitchen in nature + comfy queen bed

1 bed 1 bath
PoolA/CWiFiBalcony
$151/night
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Adorable 1-Bedroom Cottage in Weston, CT

Adorable 1-Bedroom Cottage in Weston, CT

1 bed 1 bath
PoolA/CWiFiBalcony
$196/night
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Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

2 beds 1 bath
PoolA/CWiFiBalcony
$300/night
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Historic Connecticut Home w/ Grill & Spacious Yard

Historic Connecticut Home w/ Grill & Spacious Yard

4 beds 2 baths
PoolA/CWiFiBalcony
$417/night
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Modern 4 bed 4.5 bath w hot tub & heated pool close to beach

Modern 4 bed 4.5 bath w hot tub & heated pool close to beach

5 beds 4 baths
PoolA/CWiFiBalcony
$1,040/night
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Feist House - Hot Tub + Beach Retreat in Nature

Feist House - Hot Tub + Beach Retreat in Nature

3 beds 2 baths
PoolA/CWiFiBalcony
$475/night
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Relaxing Upscale Apartment in Amazing Nature

Relaxing Upscale Apartment in Amazing Nature

2 beds 2 baths
PoolA/CWiFiBalcony
$142/night
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Charming Country Getaway on Stillwater Pond

Charming Country Getaway on Stillwater Pond

3 beds 3 baths
PoolA/CWiFiBalcony
$272/night
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Enchanting, cozy & secluded riverfront English cottage SANCTUARY

Enchanting, cozy & secluded riverfront English cottage SANCTUARY

3 beds 3 baths
PoolA/CWiFiBalcony
$462/night
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Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn

Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn

4 beds 4 baths
PoolA/CWiFiBalcony
$1,398/night
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Stunning Weston 4 bed house with swimming pool

Stunning Weston 4 bed house with swimming pool

4 beds 2 baths
PoolA/CWiFiBalcony
$699/night
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Gorgeous Weston Retreat with Tennis & Hot Tub

Gorgeous Weston Retreat with Tennis & Hot Tub

4 beds 3 baths
PoolA/CWiFiBalcony
$808/night
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Riverfront retreat in the woods of scenic Weston, Connecticut.

Riverfront retreat in the woods of scenic Weston, Connecticut.

3 beds 2 baths
PoolA/CWiFiBalcony
$438/night
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The Weston River House 1 hr from NYC Designed by Famed Artisan Michael Greenberg

The Weston River House 1 hr from NYC Designed by Famed Artisan Michael Greenberg

1 bed 1 bath
PoolA/CWiFiBalcony
$203/night
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Luxury family home w/ pool, hot tub, sauna & gym

Luxury family home w/ pool, hot tub, sauna & gym

4 beds 5 baths
PoolA/CWiFiBalcony
$848/night
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AMAMZING FAMILY FUN FILLED RETREAT

AMAMZING FAMILY FUN FILLED RETREAT

6 beds 6 baths
PoolA/CWiFiBalcony
$1,083/night
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