We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Southbury Vacation Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
49 rentals in Southbury.
Tranquil 1795 Carriage House set in two acres of gardens rimmed by forested hill, vacation rental in Southbury
Tranquil 1795 Carriage House set in two acres of gardens rimmed by forested hill, vacation rental in Southbury
Tranquil 1795 Carriage House set in two acres of gardens rimmed by forested hill, vacation rental in Southbury

Tranquil 1795 Carriage House set in two acres of gardens rimmed by forested hill

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Experience Living at the center of the Village of South Britain settled in1683, vacation rental in Southbury
Experience Living at the center of the Village of South Britain settled in1683, vacation rental in Southbury
Experience Living at the center of the Village of South Britain settled in1683, vacation rental in Southbury

Experience Living at the center of the Village of South Britain settled in1683

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Botanical Glamping, vacation rental in Southbury
Botanical Glamping, vacation rental in Southbury
Botanical Glamping, vacation rental in Southbury

Botanical Glamping

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Newly remodeled cottage on private road. Close to Lake Zoar!, vacation rental in Southbury
Newly remodeled cottage on private road. Close to Lake Zoar!, vacation rental in Southbury
Newly remodeled cottage on private road. Close to Lake Zoar!, vacation rental in Southbury

Newly remodeled cottage on private road. Close to Lake Zoar!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Apartment in Southford,Southbury, vacation rental in Southbury
Apartment in Southford,Southbury, vacation rental in Southbury
Apartment in Southford,Southbury, vacation rental in Southbury

Apartment in Southford,Southbury

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lakehouse with Amazing View, Jacuzzi, Parks, Attractions Perfect for Families, vacation rental in Southbury
Lakehouse with Amazing View, Jacuzzi, Parks, Attractions Perfect for Families, vacation rental in Southbury
Lakehouse with Amazing View, Jacuzzi, Parks, Attractions Perfect for Families, vacation rental in Southbury

Lakehouse with Amazing View, Jacuzzi, Parks, Attractions Perfect for Families

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Come live in an  elegant and spacious historic home with all of today's comforts, vacation rental in Southbury
Come live in an  elegant and spacious historic home with all of today's comforts, vacation rental in Southbury
Come live in an  elegant and spacious historic home with all of today's comforts, vacation rental in Southbury

Come live in an elegant and spacious historic home with all of today's comforts

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The following properties within 20 miles of Southbury match all your filters:
Charming 1760 Cape Nestled in the Foothills of Litchfield County, vacation rental in Southbury
Charming 1760 Cape Nestled in the Foothills of Litchfield County, vacation rental in Southbury
Charming 1760 Cape Nestled in the Foothills of Litchfield County, vacation rental in Southbury

Charming 1760 Cape Nestled in the Foothills of Litchfield County

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants, vacation rental in Southbury
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants, vacation rental in Southbury
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants, vacation rental in Southbury

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cottage at Sunny Day.  Stylish & bright 3BR/3 Bath lakefront house for every, vacation rental in Southbury
Cottage at Sunny Day.  Stylish & bright 3BR/3 Bath lakefront house for every, vacation rental in Southbury
Cottage at Sunny Day.  Stylish & bright 3BR/3 Bath lakefront house for every, vacation rental in Southbury

Cottage at Sunny Day. Stylish & bright 3BR/3 Bath lakefront house for every

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Family-Friendly Woodbury Home with Yard + Deck!, vacation rental in Southbury
Family-Friendly Woodbury Home with Yard + Deck!, vacation rental in Southbury
Family-Friendly Woodbury Home with Yard + Deck!, vacation rental in Southbury

Family-Friendly Woodbury Home with Yard + Deck!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Tranquil Villa, vacation rental in Southbury
Tranquil Villa, vacation rental in Southbury
Tranquil Villa, vacation rental in Southbury

Tranquil Villa

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Airstream Retreat on The Farm, vacation rental in Southbury
Airstream Retreat on The Farm, vacation rental in Southbury
Airstream Retreat on The Farm, vacation rental in Southbury

Airstream Retreat on The Farm

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Traveler’s Dream On Bike Path! Close to Highway, Hospitals, and Schools., vacation rental in Southbury
Traveler’s Dream On Bike Path! Close to Highway, Hospitals, and Schools., vacation rental in Southbury
Traveler’s Dream On Bike Path! Close to Highway, Hospitals, and Schools., vacation rental in Southbury

Traveler’s Dream On Bike Path! Close to Highway, Hospitals, and Schools.

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Waterfront Retreat w/ Boat Dock & Fire Pit!, vacation rental in Southbury
Waterfront Retreat w/ Boat Dock & Fire Pit!, vacation rental in Southbury
Waterfront Retreat w/ Boat Dock & Fire Pit!, vacation rental in Southbury

Waterfront Retreat w/ Boat Dock & Fire Pit!

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
New Listing!  The Cozy Moose,  Newtown CT - 1 bdr Log Cabin, Pool, Hiking, vacation rental in Southbury
New Listing!  The Cozy Moose,  Newtown CT - 1 bdr Log Cabin, Pool, Hiking, vacation rental in Southbury
New Listing!  The Cozy Moose,  Newtown CT - 1 bdr Log Cabin, Pool, Hiking, vacation rental in Southbury

New Listing! The Cozy Moose, Newtown CT - 1 bdr Log Cabin, Pool, Hiking

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Spacious 1 Bedroom Apartment, vacation rental in Southbury
Spacious 1 Bedroom Apartment, vacation rental in Southbury
Spacious 1 Bedroom Apartment, vacation rental in Southbury

Spacious 1 Bedroom Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN" Ski,Pool,BBQ,Magical!, vacation rental in Southbury
BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN" Ski,Pool,BBQ,Magical!, vacation rental in Southbury
BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT "TOPHET POOL BARN" Ski,Pool,BBQ,Magical!, vacation rental in Southbury

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

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming Country Cottage, vacation rental in Southbury
Charming Country Cottage, vacation rental in Southbury
Charming Country Cottage, vacation rental in Southbury

Charming Country Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lakefront home with great outdoor space, vacation rental in Southbury
Lakefront home with great outdoor space, vacation rental in Southbury
Lakefront home with great outdoor space, vacation rental in Southbury

Lakefront home with great outdoor space

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Rustic Three bedroom , 2 full bath Bungalow, vacation rental in Southbury
Rustic Three bedroom , 2 full bath Bungalow, vacation rental in Southbury
Rustic Three bedroom , 2 full bath Bungalow, vacation rental in Southbury

Rustic Three bedroom , 2 full bath Bungalow

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Sunset Living, vacation rental in Southbury
Sunset Living, vacation rental in Southbury
Sunset Living, vacation rental in Southbury

Sunset Living

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cheerful 3-4 bedroom home with all the updates, vacation rental in Southbury
Cheerful 3-4 bedroom home with all the updates, vacation rental in Southbury
Cheerful 3-4 bedroom home with all the updates, vacation rental in Southbury

Cheerful 3-4 bedroom home with all the updates

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Home away from home, vacation rental in Southbury
Home away from home, vacation rental in Southbury
Home away from home, vacation rental in Southbury

Home away from home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Twilight Dreams Farm, vacation rental in Southbury
Twilight Dreams Farm, vacation rental in Southbury
Twilight Dreams Farm, vacation rental in Southbury

Twilight Dreams Farm

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Stay at the charming Farmhouse Table, vacation rental in Southbury
Stay at the charming Farmhouse Table, vacation rental in Southbury
Stay at the charming Farmhouse Table, vacation rental in Southbury

Stay at the charming Farmhouse Table

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
A place of silence, close to NYC, vacation rental in Southbury
A place of silence, close to NYC, vacation rental in Southbury
A place of silence, close to NYC, vacation rental in Southbury

A place of silence, close to NYC

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Amazing Lake House, vacation rental in Southbury
Amazing Lake House, vacation rental in Southbury
Amazing Lake House, vacation rental in Southbury

Amazing Lake House

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Classic Roxbury Home w/ Picturesque Backyard!, vacation rental in Southbury
Classic Roxbury Home w/ Picturesque Backyard!, vacation rental in Southbury
Classic Roxbury Home w/ Picturesque Backyard!, vacation rental in Southbury

Classic Roxbury Home w/ Picturesque Backyard!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Make lifelong memories at this New England Quintessential Country Getaway, vacation rental in Southbury
Make lifelong memories at this New England Quintessential Country Getaway, vacation rental in Southbury
Make lifelong memories at this New England Quintessential Country Getaway, vacation rental in Southbury

Make lifelong memories at this New England Quintessential Country Getaway

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Litchfield County home on CT Antiques and CT Wine Trail!, vacation rental in Southbury
Litchfield County home on CT Antiques and CT Wine Trail!, vacation rental in Southbury
Litchfield County home on CT Antiques and CT Wine Trail!, vacation rental in Southbury

Litchfield County home on CT Antiques and CT Wine Trail!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
BEST TOWN ROXBURY! PoshPadsCT"TOPHET 3BR"Ski,Heated Winter Pool/Spa,Bikes,GasBBQ, vacation rental in Southbury
BEST TOWN ROXBURY! PoshPadsCT"TOPHET 3BR"Ski,Heated Winter Pool/Spa,Bikes,GasBBQ, vacation rental in Southbury
BEST TOWN ROXBURY! PoshPadsCT"TOPHET 3BR"Ski,Heated Winter Pool/Spa,Bikes,GasBBQ, vacation rental in Southbury

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!, vacation rental in Southbury
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!, vacation rental in Southbury
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!, vacation rental in Southbury

Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Beautiful Country House 1 mile from town, vacation rental in Southbury
Beautiful Country House 1 mile from town, vacation rental in Southbury
Beautiful Country House 1 mile from town, vacation rental in Southbury

Beautiful Country House 1 mile from town

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat, vacation rental in Southbury
Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat, vacation rental in Southbury
Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat, vacation rental in Southbury

Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ, Ski,Hike,1.5HrsNYC, vacation rental in Southbury
BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ, Ski,Hike,1.5HrsNYC, vacation rental in Southbury
BEST LOCATION! PoshPadsCT"PAINTER HILL4BR" Hot Tub Spa, BBQ, Ski,Hike,1.5HrsNYC, vacation rental in Southbury

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Hidden Quarry Country Home, vacation rental in Southbury
Hidden Quarry Country Home, vacation rental in Southbury
Hidden Quarry Country Home, vacation rental in Southbury

Hidden Quarry Country Home

Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Spacious Woodbury Home w/ Pool + Hot Tub!, vacation rental in Southbury
Spacious Woodbury Home w/ Pool + Hot Tub!, vacation rental in Southbury
Spacious Woodbury Home w/ Pool + Hot Tub!, vacation rental in Southbury

Spacious Woodbury Home w/ Pool + Hot Tub!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Beautiful Country Estate with Heated Pool, vacation rental in Southbury
Beautiful Country Estate with Heated Pool, vacation rental in Southbury
Beautiful Country Estate with Heated Pool, vacation rental in Southbury

Beautiful Country Estate with Heated Pool

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friend, vacation rental in Southbury
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friend, vacation rental in Southbury
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friend, vacation rental in Southbury

Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friend

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Direct Lakefront Home on Lake Lillinonah with Elevator Access, vacation rental in Southbury
Direct Lakefront Home on Lake Lillinonah with Elevator Access, vacation rental in Southbury
Direct Lakefront Home on Lake Lillinonah with Elevator Access, vacation rental in Southbury

Direct Lakefront Home on Lake Lillinonah with Elevator Access

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Chic Antique Retreat House, vacation rental in Southbury
The Chic Antique Retreat House, vacation rental in Southbury
The Chic Antique Retreat House, vacation rental in Southbury

The Chic Antique Retreat House

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
6-Acre Luxurious Country Home with Goddess Point Lookout, vacation rental in Southbury
6-Acre Luxurious Country Home with Goddess Point Lookout, vacation rental in Southbury
6-Acre Luxurious Country Home with Goddess Point Lookout, vacation rental in Southbury

6-Acre Luxurious Country Home with Goddess Point Lookout

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Tranquil Luxury in Newtown - Hot Tub, Wood Pizza Oven, Breathtaking Views, vacation rental in Southbury
Tranquil Luxury in Newtown - Hot Tub, Wood Pizza Oven, Breathtaking Views, vacation rental in Southbury
Tranquil Luxury in Newtown - Hot Tub, Wood Pizza Oven, Breathtaking Views, vacation rental in Southbury

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Litchfield County Four Season Country Paradise, vacation rental in Southbury
Litchfield County Four Season Country Paradise, vacation rental in Southbury
Litchfield County Four Season Country Paradise, vacation rental in Southbury

Litchfield County Four Season Country Paradise

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Newly Listed PRIVATE Lakefront Retreat - Pool, Hot Tub, Pet Considered, Sleeps, vacation rental in Southbury
Newly Listed PRIVATE Lakefront Retreat - Pool, Hot Tub, Pet Considered, Sleeps, vacation rental in Southbury
Newly Listed PRIVATE Lakefront Retreat - Pool, Hot Tub, Pet Considered, Sleeps, vacation rental in Southbury

Newly Listed PRIVATE Lakefront Retreat - Pool, Hot Tub, Pet Considered, Sleeps

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Exclusive Lakefront Getaway - Pool, Hot Tub, Stunning Views, vacation rental in Southbury
Exclusive Lakefront Getaway - Pool, Hot Tub, Stunning Views, vacation rental in Southbury
Exclusive Lakefront Getaway - Pool, Hot Tub, Stunning Views, vacation rental in Southbury

Exclusive Lakefront Getaway - Pool, Hot Tub, Stunning Views

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Nature & Luxury *Lavender Lake Est (Kosher optional), vacation rental in Southbury
Nature & Luxury *Lavender Lake Est (Kosher optional), vacation rental in Southbury
Nature & Luxury *Lavender Lake Est (Kosher optional), vacation rental in Southbury

Nature & Luxury *Lavender Lake Est (Kosher optional)

Rental Home
7 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
2 Bedroom Suite with Kitchen, vacation rental in Southbury
2 Bedroom Suite with Kitchen, vacation rental in Southbury
2 Bedroom Suite with Kitchen, vacation rental in Southbury

2 Bedroom Suite with Kitchen

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Showing results 1-49 of 49
Frequently Asked Questions about Southbury