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Holiday Rentals in Southbury

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
49 rentals in Southbury.
Remodeled 1795 Carriage House with two acres of gardens rimmed by forests, holiday rental in Southbury
Remodeled 1795 Carriage House with two acres of gardens rimmed by forests, holiday rental in Southbury
Remodeled 1795 Carriage House with two acres of gardens rimmed by forests, holiday rental in Southbury

Remodeled 1795 Carriage House with two acres of gardens rimmed by forests

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Romantic Botanical Glamping with pool, gardens & smoked dinner for 2 available., holiday rental in Southbury
Romantic Botanical Glamping with pool, gardens & smoked dinner for 2 available., holiday rental in Southbury
Romantic Botanical Glamping with pool, gardens & smoked dinner for 2 available., holiday rental in Southbury

Romantic Botanical Glamping with pool, gardens & smoked dinner for 2 available.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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One Bedroom Apartment in Southford/Southbury, CT, holiday rental in Southbury
One Bedroom Apartment in Southford/Southbury, CT, holiday rental in Southbury
One Bedroom Apartment in Southford/Southbury, CT, holiday rental in Southbury

One Bedroom Apartment in Southford/Southbury, CT

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Clean & Bright 2 Bedroom Cottage shares 8 Acres, holiday rental in Southbury
Clean & Bright 2 Bedroom Cottage shares 8 Acres, holiday rental in Southbury
Clean & Bright 2 Bedroom Cottage shares 8 Acres, holiday rental in Southbury

Clean & Bright 2 Bedroom Cottage shares 8 Acres

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy family and pet friendly 3BR Home, holiday rental in Southbury
Cozy family and pet friendly 3BR Home, holiday rental in Southbury
Cozy family and pet friendly 3BR Home, holiday rental in Southbury

Cozy family and pet friendly 3BR Home

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Soak in the Lake Views at the Spacious Waterfront Apartment, holiday rental in Southbury
Soak in the Lake Views at the Spacious Waterfront Apartment, holiday rental in Southbury
Soak in the Lake Views at the Spacious Waterfront Apartment, holiday rental in Southbury

Soak in the Lake Views at the Spacious Waterfront Apartment

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Lakefront studio with panoramic lake views., holiday rental in Southbury
Charming Lakefront studio with panoramic lake views., holiday rental in Southbury
Charming Lakefront studio with panoramic lake views., holiday rental in Southbury

Charming Lakefront studio with panoramic lake views.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming bungalow in lovely Southbury with panoramic lakefront views, holiday rental in Southbury
Charming bungalow in lovely Southbury with panoramic lakefront views, holiday rental in Southbury
Charming bungalow in lovely Southbury with panoramic lakefront views, holiday rental in Southbury

Charming bungalow in lovely Southbury with panoramic lakefront views

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront View - Unit F, holiday rental in Southbury
Waterfront View - Unit F, holiday rental in Southbury
Waterfront View - Unit F, holiday rental in Southbury

Waterfront View - Unit F

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury, holiday rental in Southbury
Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury, holiday rental in Southbury
Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury, holiday rental in Southbury

Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Apartment in Southford,Southbury, holiday rental in Southbury
Apartment in Southford,Southbury, holiday rental in Southbury
Apartment in Southford,Southbury, holiday rental in Southbury

Apartment in Southford,Southbury

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy cute Relaxing home, holiday rental in Southbury
Cozy cute Relaxing home, holiday rental in Southbury
Cozy cute Relaxing home, holiday rental in Southbury

Cozy cute Relaxing home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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The following properties within 32 kms of Southbury match all your filters:
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants, holiday rental in Southbury
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants, holiday rental in Southbury
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants, holiday rental in Southbury

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern, holiday rental in Southbury
Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern, holiday rental in Southbury
Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern, holiday rental in Southbury

Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful, Fun Lakefront Retreat -- Perfect for family reunions /  groups, holiday rental in Southbury
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions /  groups, holiday rental in Southbury
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions /  groups, holiday rental in Southbury

Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Family-Friendly Woodbury Home with Yard + Deck!, holiday rental in Southbury
Family-Friendly Woodbury Home with Yard + Deck!, holiday rental in Southbury
Family-Friendly Woodbury Home with Yard + Deck!, holiday rental in Southbury

Family-Friendly Woodbury Home with Yard + Deck!

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Airstream Retreat on The Farm, holiday rental in Southbury
Airstream Retreat on The Farm, holiday rental in Southbury
Airstream Retreat on The Farm, holiday rental in Southbury

Airstream Retreat on The Farm

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Retreat w/ Boat Dock & Fire Pit!, holiday rental in Southbury
Waterfront Retreat w/ Boat Dock & Fire Pit!, holiday rental in Southbury
Waterfront Retreat w/ Boat Dock & Fire Pit!, holiday rental in Southbury

Waterfront Retreat w/ Boat Dock & Fire Pit!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Peaceful apartment on 3.5 acres w/ artist studio., holiday rental in Southbury
Peaceful apartment on 3.5 acres w/ artist studio., holiday rental in Southbury
Peaceful apartment on 3.5 acres w/ artist studio., holiday rental in Southbury

Peaceful apartment on 3.5 acres w/ artist studio.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat, holiday rental in Southbury
Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat, holiday rental in Southbury
Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat, holiday rental in Southbury

Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN, holiday rental in Southbury
BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN, holiday rental in Southbury
BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN, holiday rental in Southbury

BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Country Cottage, holiday rental in Southbury
Charming Country Cottage, holiday rental in Southbury
Charming Country Cottage, holiday rental in Southbury

Charming Country Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront home with great outdoor space, holiday rental in Southbury
Lakefront home with great outdoor space, holiday rental in Southbury
Lakefront home with great outdoor space, holiday rental in Southbury

Lakefront home with great outdoor space

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Rustic Three bedroom , 2 full bath Bungalow, holiday rental in Southbury
Rustic Three bedroom , 2 full bath Bungalow, holiday rental in Southbury
Rustic Three bedroom , 2 full bath Bungalow, holiday rental in Southbury

Rustic Three bedroom , 2 full bath Bungalow

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Living, holiday rental in Southbury
Sunset Living, holiday rental in Southbury
Sunset Living, holiday rental in Southbury

Sunset Living

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Cheerful 4 bedroom home with all the updates, holiday rental in Southbury
Cheerful 4 bedroom home with all the updates, holiday rental in Southbury
Cheerful 4 bedroom home with all the updates, holiday rental in Southbury

Cheerful 4 bedroom home with all the updates

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Home away from home, holiday rental in Southbury
Home away from home, holiday rental in Southbury
Home away from home, holiday rental in Southbury

Home away from home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Twilight Dreams Farm, holiday rental in Southbury
Twilight Dreams Farm, holiday rental in Southbury
Twilight Dreams Farm, holiday rental in Southbury

Twilight Dreams Farm

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A place of silence, close to NYC, holiday rental in Southbury
A place of silence, close to NYC, holiday rental in Southbury
A place of silence, close to NYC, holiday rental in Southbury

A place of silence, close to NYC

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Amazing Lake House, holiday rental in Southbury
Amazing Lake House, holiday rental in Southbury
Amazing Lake House, holiday rental in Southbury

Amazing Lake House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Classic Roxbury Home w/ Picturesque Backyard!, holiday rental in Southbury
Classic Roxbury Home w/ Picturesque Backyard!, holiday rental in Southbury
Classic Roxbury Home w/ Picturesque Backyard!, holiday rental in Southbury

Classic Roxbury Home w/ Picturesque Backyard!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Make lifelong memories at this New England Quintessential Country Getaway, holiday rental in Southbury
Make lifelong memories at this New England Quintessential Country Getaway, holiday rental in Southbury
Make lifelong memories at this New England Quintessential Country Getaway, holiday rental in Southbury

Make lifelong memories at this New England Quintessential Country Getaway

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BEST TOWN ROXBURY! PoshPadsCT"TOPHET 3BR"Ski,Heated Winter, holiday rental in Southbury
BEST TOWN ROXBURY! PoshPadsCT"TOPHET 3BR"Ski,Heated Winter, holiday rental in Southbury
BEST TOWN ROXBURY! PoshPadsCT"TOPHET 3BR"Ski,Heated Winter, holiday rental in Southbury

BEST TOWN ROXBURY! PoshPadsCT"TOPHET 3BR"Ski,Heated Winter

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!, holiday rental in Southbury
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!, holiday rental in Southbury
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!, holiday rental in Southbury

Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Country House 1 mile from town, holiday rental in Southbury
Beautiful Country House 1 mile from town, holiday rental in Southbury
Beautiful Country House 1 mile from town, holiday rental in Southbury

Beautiful Country House 1 mile from town

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ, holiday rental in Southbury
BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ, holiday rental in Southbury
BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ, holiday rental in Southbury

BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Woodbury Home w/ Pool + Hot Tub!, holiday rental in Southbury
Spacious Woodbury Home w/ Pool + Hot Tub!, holiday rental in Southbury
Spacious Woodbury Home w/ Pool + Hot Tub!, holiday rental in Southbury

Spacious Woodbury Home w/ Pool + Hot Tub!

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Country Estate with Heated Pool, holiday rental in Southbury
Beautiful Country Estate with Heated Pool, holiday rental in Southbury
Beautiful Country Estate with Heated Pool, holiday rental in Southbury

Beautiful Country Estate with Heated Pool

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Direct Lakefront Home on Lake Lillinonah with Elevator Access, holiday rental in Southbury
Direct Lakefront Home on Lake Lillinonah with Elevator Access, holiday rental in Southbury
Direct Lakefront Home on Lake Lillinonah with Elevator Access, holiday rental in Southbury

Direct Lakefront Home on Lake Lillinonah with Elevator Access

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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6-Acre Luxurious Country Home with Goddess Point Lookout, holiday rental in Southbury
6-Acre Luxurious Country Home with Goddess Point Lookout, holiday rental in Southbury
6-Acre Luxurious Country Home with Goddess Point Lookout, holiday rental in Southbury

6-Acre Luxurious Country Home with Goddess Point Lookout

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Litchfield County Four Season Country Paradise, holiday rental in Southbury
Litchfield County Four Season Country Paradise, holiday rental in Southbury
Litchfield County Four Season Country Paradise, holiday rental in Southbury

Litchfield County Four Season Country Paradise

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Sunny Day on Taunton Lake: Exclusive Lakefront Retreat with Pool, Hot Tub, Gym, holiday rental in Southbury
Sunny Day on Taunton Lake: Exclusive Lakefront Retreat with Pool, Hot Tub, Gym, holiday rental in Southbury
Sunny Day on Taunton Lake: Exclusive Lakefront Retreat with Pool, Hot Tub, Gym, holiday rental in Southbury

Sunny Day on Taunton Lake: Exclusive Lakefront Retreat with Pool, Hot Tub, Gym

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Nature & Luxury *Lavender Lake Est (Kosher optional), holiday rental in Southbury
Nature & Luxury *Lavender Lake Est (Kosher optional), holiday rental in Southbury
Nature & Luxury *Lavender Lake Est (Kosher optional), holiday rental in Southbury

Nature & Luxury *Lavender Lake Est (Kosher optional)

Holiday Rental House
9 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Tranquil Luxury in Newtown - Hot Tub, Wood Pizza Oven, Breathtaking Views, holiday rental in Southbury
Tranquil Luxury in Newtown - Hot Tub, Wood Pizza Oven, Breathtaking Views, holiday rental in Southbury
Tranquil Luxury in Newtown - Hot Tub, Wood Pizza Oven, Breathtaking Views, holiday rental in Southbury

Tranquil Luxury in Newtown - Hot Tub, Wood Pizza Oven, Breathtaking Views

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming Saltbox Colonial with Modern Amenities, holiday rental in Southbury
Charming Saltbox Colonial with Modern Amenities, holiday rental in Southbury
Charming Saltbox Colonial with Modern Amenities, holiday rental in Southbury

Charming Saltbox Colonial with Modern Amenities

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Colonial yellowhouse, holiday rental in Southbury
Colonial yellowhouse, holiday rental in Southbury
Colonial yellowhouse, holiday rental in Southbury

Colonial yellowhouse

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Quiet, cozy Loft Apartment in country setting. Great escape to Litchfield Hills!, holiday rental in Southbury
Quiet, cozy Loft Apartment in country setting. Great escape to Litchfield Hills!, holiday rental in Southbury
Quiet, cozy Loft Apartment in country setting. Great escape to Litchfield Hills!, holiday rental in Southbury

Quiet, cozy Loft Apartment in country setting. Great escape to Litchfield Hills!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Connecticut Oasis - Updates throughout, holiday rental in Southbury
Lakefront Connecticut Oasis - Updates throughout, holiday rental in Southbury
Lakefront Connecticut Oasis - Updates throughout, holiday rental in Southbury

Lakefront Connecticut Oasis - Updates throughout

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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STUNNING Home on 3 acre Private Pond w. Hot Tub, BBQ, Firepit, holiday rental in Southbury
STUNNING Home on 3 acre Private Pond w. Hot Tub, BBQ, Firepit, holiday rental in Southbury
STUNNING Home on 3 acre Private Pond w. Hot Tub, BBQ, Firepit, holiday rental in Southbury

STUNNING Home on 3 acre Private Pond w. Hot Tub, BBQ, Firepit

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Showing results 1-49 of 49
Frequently Asked Questions about Southbury