Roxbury, Connecticut

Vacation Rentals in Roxbury, Connecticut

Discover 17 vacation rental properties in Roxbury. From 1 to 7 bedrooms. Average $891/night. 100% have pools.

17 verified listings Book securely on VRBO Prices updated March 2026

17 properties available

Within a walking distance of hiking trails and a short drive to Lake Waramaug.

Within a walking distance of hiking trails and a short drive to Lake Waramaug.

3 beds 2 baths
PoolA/CWiFiBalcony
$253/night
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Twilight Dreams Farm

Twilight Dreams Farm

3 beds 2 baths
PoolA/CWiFiBalcony
$458/night
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BEST TOWN ROXBURY! PoshPadsCT "247 PAINTER" 1.5Hrs NYC, Mint, Ski, Fires, BBQ

BEST TOWN ROXBURY! PoshPadsCT "247 PAINTER" 1.5Hrs NYC, Mint, Ski, Fires, BBQ

4 beds 4 baths
PoolA/CWiFiBalcony
$1,100/night
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BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN" Ski,Pool,BBQ,Magical!

BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN" Ski,Pool,BBQ,Magical!

1 bed 1 bath
PoolA/CWiFiBalcony
$818/night
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BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ, Ski,Hike,1.5HrsNYC

BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ, Ski,Hike,1.5HrsNYC

4 beds 3 baths
PoolA/CWiFiBalcony
$781/night
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ROXBURY BEST LOCATION! PoshPadsCT"PAINTER RIDGE"Mint3BR,Pool,BBQ,Bike,1.5HrsNYC

ROXBURY BEST LOCATION! PoshPadsCT"PAINTER RIDGE"Mint3BR,Pool,BBQ,Bike,1.5HrsNYC

3 beds 3 baths
PoolA/CWiFiBalcony
$1,033/night
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100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ

100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ

5 beds 3 baths
PoolA/CWiFiBalcony
$1,214/night
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BEST TOWN ROXBURY! PoshPadsCT"TOPHET 3BR"Ski,Heated Winter Pool/Spa,Bikes,GasBBQ

BEST TOWN ROXBURY! PoshPadsCT"TOPHET 3BR"Ski,Heated Winter Pool/Spa,Bikes,GasBBQ

3 beds 2 baths
PoolA/CWiFiBalcony
$933/night
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Lovely Home on Private Pond w. Hot Tub, Outdoor Shower

Lovely Home on Private Pond w. Hot Tub, Outdoor Shower

3 beds 2 baths
PoolA/CWiFiBalcony
$699/night
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BEST TOWN! PoshPadsCT "TUNNEL" Ski!, 4-BR SPA-POOL, Bike, Hiking, NYC 1.5 Hrs

BEST TOWN! PoshPadsCT "TUNNEL" Ski!, 4-BR SPA-POOL, Bike, Hiking, NYC 1.5 Hrs

4 beds 2 baths
PoolA/CWiFiBalcony
$1,040/night
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Cheerful 4 Bedroom Country Home w/Pool on 3.5 acres. Near cute towns & hiking!

Cheerful 4 Bedroom Country Home w/Pool on 3.5 acres. Near cute towns & hiking!

4 beds 3 baths
PoolA/CWiFiBalcony
$549/night
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Charming country home in Roxbury

Charming country home in Roxbury

3 beds 1 bath
PoolA/CWiFiBalcony
$401/night
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100% ROXBURY! PoshPadsCT "SENTRY HILL" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ

100% ROXBURY! PoshPadsCT "SENTRY HILL" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ

6 beds 3 baths
PoolA/CWiFiBalcony
$1,322/night
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Classic Roxbury Home w/ Picturesque Backyard!

Classic Roxbury Home w/ Picturesque Backyard!

3 beds 2 baths
PoolA/CWiFiBalcony
$380/night
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100% ROXBURY! PoshPadsCT "MOOSEHORN" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes

100% ROXBURY! PoshPadsCT "MOOSEHORN" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes

6 beds 4 baths
PoolA/CWiFiBalcony
$1,398/night
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Litchfield County Four Season Country Paradise

Litchfield County Four Season Country Paradise

5 beds 4 baths
PoolA/CWiFiBalcony
$939/night
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Nature & Luxury @Lavender Lake Est (Kosher optional)

Nature & Luxury @Lavender Lake Est (Kosher optional)

7 beds 4 baths
PoolA/CWiFiBalcony
$1,833/night
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More destinations in Connecticut

New Haven (158) Stonington (135) Milford (100) Mystic (93) Stamford (84) Old Saybrook (82) Westbrook (74) Old Lyme (71) Fairfield (57) Madison (56) Westport (55) Branford (53) Norwich (52) Greenwich (52) Groton (51) Bridgeport (47) East Lyme (43) Clinton (42) Hartford (40) Guilford (38)