New Fairfield, Connecticut

Vacation Rentals in New Fairfield, Connecticut

Discover 37 vacation rental properties in New Fairfield. From 1 to 6 bedrooms. Average $548/night. 100% have pools.

37 verified listings Book securely on VRBO Prices updated March 2026

37 properties available

Sunrise Bungalow - Lake and Mountains View

Sunrise Bungalow - Lake and Mountains View

2 beds 1 bath
PoolA/CWiFiBalcony
$217/night
View Details → Book on VRBO
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond

4 beds 2 baths
PoolA/CWiFiBalcony
$396/night
View Details → Book on VRBO
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC

Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC

1 bed 1 bath
PoolA/CWiFiBalcony
$197/night
View Details → Book on VRBO
Candlewood Cabin - with Private Waterfront

Candlewood Cabin - with Private Waterfront

2 beds 1 bath
PoolA/CWiFiBalcony
$316/night
View Details → Book on VRBO
Lakefront Cabin w/Dock, Fire Pit and Private Beach on Quiet Candlewood Lake Cove

Lakefront Cabin w/Dock, Fire Pit and Private Beach on Quiet Candlewood Lake Cove

2 beds 2 baths
PoolA/CWiFiBalcony
$555/night
View Details → Book on VRBO
Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball

Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball

3 beds 2 baths
PoolA/CWiFiBalcony
$349/night
View Details → Book on VRBO
Lakehouse Cottage w/ Boat Dock Kayaks 1 Hour & 15 Min from NYC on Squantz Pond

Lakehouse Cottage w/ Boat Dock Kayaks 1 Hour & 15 Min from NYC on Squantz Pond

2 beds 1 bath
PoolA/CWiFiBalcony
$333/night
View Details → Book on VRBO
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.

Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.

3 beds 2 baths
PoolA/CWiFiBalcony
$550/night
View Details → Book on VRBO
3 BR Lake House in Private Candlewood Lake Community

3 BR Lake House in Private Candlewood Lake Community

3 beds 1 bath
PoolA/CWiFiBalcony
$291/night
View Details → Book on VRBO
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

3 beds 2 baths
PoolA/CWiFiBalcony
$286/night
View Details → Book on VRBO
Serene island retreat with a private dock on Candlewood lake

Serene island retreat with a private dock on Candlewood lake

4 beds 3 baths
PoolA/CWiFiBalcony
$622/night
View Details → Book on VRBO
Charming lake side retreat

Charming lake side retreat

4 beds 2 baths
PoolA/CWiFiBalcony
$499/night
View Details → Book on VRBO
Cozy 2-bedroom Cabin getaway in a Lake town of New Fairfield

Cozy 2-bedroom Cabin getaway in a Lake town of New Fairfield

2 beds 1 bath
PoolA/CWiFiBalcony
$329/night
View Details → Book on VRBO
New Fairfield Home w/ Beach Access & Fire Pit

New Fairfield Home w/ Beach Access & Fire Pit

2 beds 1 bath
PoolA/CWiFiBalcony
$234/night
View Details → Book on VRBO
Cozy one bedroom apartment in New Fairfield with restorative activities.

Cozy one bedroom apartment in New Fairfield with restorative activities.

1 bed 1 bath
PoolA/CWiFiBalcony
$100/night
View Details → Book on VRBO
REDUCED FOR AFTER LABOR DAY - Waterfront cottage on Candlewood Lake

REDUCED FOR AFTER LABOR DAY - Waterfront cottage on Candlewood Lake

3 beds 1 bath
PoolA/CWiFiBalcony
$739/night
View Details → Book on VRBO
New Modern Candlewood Lake House Retreat-Getaway

New Modern Candlewood Lake House Retreat-Getaway

2 beds 2 baths
PoolA/CWiFiBalcony
$274/night
View Details → Book on VRBO
Enjoy Candlewood Lake in Gorgeous, Open Family Home

Enjoy Candlewood Lake in Gorgeous, Open Family Home

6 beds 5 baths
PoolA/CWiFiBalcony
$649/night
View Details → Book on VRBO
Peaceful All Season Lake Community Home

Peaceful All Season Lake Community Home

3 beds 2 baths
PoolA/CWiFiBalcony
$405/night
View Details → Book on VRBO
Position "A"........Perfect Family Get Away

Position "A"........Perfect Family Get Away

3 beds 2 baths
PoolA/CWiFiBalcony
$502/night
View Details → Book on VRBO
Serene Lakefront Getaway - Luxurious Candlewood Knolls Retreat with Private Dock

Serene Lakefront Getaway - Luxurious Candlewood Knolls Retreat with Private Dock

4 beds 2 baths
PoolA/CWiFiBalcony
$808/night
View Details → Book on VRBO
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

3 beds 3 baths
PoolA/CWiFiBalcony
$437/night
View Details → Book on VRBO
Aug prime weeks now available-Best Direct Lakefront Location on Candlewood

Aug prime weeks now available-Best Direct Lakefront Location on Candlewood

5 beds 3 baths
PoolA/CWiFiBalcony
$655/night
View Details → Book on VRBO
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC

Sweet Dotti's Cottage on Candlewood Lake - 60M NYC

4 beds 2 baths
PoolA/CWiFiBalcony
$395/night
View Details → Book on VRBO
Family Friendly/Direct Waterfront/Chefs indoor & outdoor kitchen/3 fireplaces

Family Friendly/Direct Waterfront/Chefs indoor & outdoor kitchen/3 fireplaces

5 beds 5 baths
PoolA/CWiFiBalcony
$1,598/night
View Details → Book on VRBO
Lakefront Luxury Retreat on Candlewood Lake

Lakefront Luxury Retreat on Candlewood Lake

5 beds 3 baths
PoolA/CWiFiBalcony
$1,505/night
View Details → Book on VRBO
Dream waterfront lake house with history, charm and beauty, On Candlewood Isle.

Dream waterfront lake house with history, charm and beauty, On Candlewood Isle.

4 beds 3 baths
PoolA/CWiFiBalcony
$862/night
View Details → Book on VRBO
Amazing Adirondack Candlewood Lake Front

Amazing Adirondack Candlewood Lake Front

3 beds 4 baths
PoolA/CWiFiBalcony
$1,054/night
View Details → Book on VRBO
New Fairfield Vacation Rental w/ Lake Views!

New Fairfield Vacation Rental w/ Lake Views!

3 beds 2 baths
PoolA/CWiFiBalcony
$488/night
View Details → Book on VRBO
New Fairfield Vacation Rental w/ Lake Views!

New Fairfield Vacation Rental w/ Lake Views!

1 bed 1 bath
PoolA/CWiFiBalcony
$288/night
View Details → Book on VRBO
Beautiful Lakefront Retreat

Beautiful Lakefront Retreat

3 beds 2 baths
PoolA/CWiFiBalcony
$193/night
View Details → Book on VRBO
Cheerful home with amazing lake view

Cheerful home with amazing lake view

3 beds 1 bath
PoolA/CWiFiBalcony
$173/night
View Details → Book on VRBO
The Lookout on Candlewood Lake

The Lookout on Candlewood Lake

3 beds 3 baths
PoolA/CWiFiBalcony
$331/night
View Details → Book on VRBO
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

6 beds 3 baths
PoolA/CWiFiBalcony
$1,474/night
View Details → Book on VRBO
Sunberm Earthen Home- Healing Your Body & Soul Reconnecting with the Earth

Sunberm Earthen Home- Healing Your Body & Soul Reconnecting with the Earth

3 beds 2 baths
PoolA/CWiFiBalcony
$1,262/night
View Details → Book on VRBO
Lake View Cottage in Candlewood Lake Community

Lake View Cottage in Candlewood Lake Community

3 beds 2 baths
PoolA/CWiFiBalcony
$376/night
View Details → Book on VRBO
Gorgeous Candlewood Isle Lake View Home

Gorgeous Candlewood Isle Lake View Home

3 beds 3 baths
PoolA/CWiFiBalcony
$549/night
View Details → Book on VRBO

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)