Book Holiday Homes in Southbury

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Featured Holiday Homes in Southbury

Historic Connecticut Home w/ Grill & Spacious Yard

Historic Connecticut Home w/ Grill & Spacious Yard

Weston
When you stay at this vacation home in Weston, you'll be within a 10-minute drive of Wilton Historical Society and Westport Historical Society.
Historic Connecticut Home w/ Grill & Spacious Yard
Lakeside luxury: beautiful, relaxing 4 bedroom home

Lakeside luxury: beautiful, relaxing 4 bedroom home

Trumbull
With a stay at this vacation home in Trumbull, you'll be within a 10-minute drive of Northeast Medical Group and Roosevelt Forest.
Lakeside luxury: beautiful, relaxing 4 bedroom home
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Danbury
Located in Danbury, this vacation home is on the waterfront, a 1-minute drive from Candlewood Lake and 7 minutes from Candlewood Plaza Shopping Center.
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
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Stylish & Luxurious 3 BDR Home with Play Station

Stylish & Luxurious 3 BDR Home with Play Station

Bristol
With a stay at this vacation home in Bristol, you'll be within a 5-minute drive of Seymour Park and Bristol Commons Shopping Center.
Stylish & Luxurious 3 BDR Home with Play Station
Business or Weekend escape

Business or Weekend escape

Stratford
The price is AU$219 per night from 7 Apr to 8 Apr
AU$219
includes taxes & fees
7 Apr - 8 Apr
Located in Stratford, this vacation home is within a 5-minute drive of Perry House and Stratford Historical Society Capt David Judson House.
Business or Weekend escape
Cheerful 4 bedrooms residential house.

Cheerful 4 bedrooms residential house.

Bridgeport
When you a stay at this vacation home in Bridgeport, you'll be by the sea, just steps from Bridgeport Downtown South Historic District and University of ...
Cheerful 4 bedrooms residential house.
Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views

Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views

Plymouth
Located in Terryville, this vacation home is on the waterfront, within a 10-minute drive of Cedar Lake and Imagine Nation Children's Museum.
Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

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

New Fairfield
Located in New Fairfield, this vacation home is on the waterfront, a 1-minute drive from Candlewood Lake and 7 minutes from Squantz Pond State Park.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Tranquil Litchfield Connecticut Retreat".

Tranquil Litchfield Connecticut Retreat".

Litchfield
The price is AU$502 per night from 2 Apr to 3 Apr
AU$502
includes taxes & fees
2 Apr - 3 Apr
This vacation home is 4.1 mi (6.6 km) from Black Rock State Park and 6.3 mi (10.1 km) from Haight-Brown Vineyard.
Tranquil Litchfield Connecticut Retreat".
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Southbury Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Southbury vacation homes are the perfect way for you to wing it.

Holiday houses in Southbury let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Southbury in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Southbury adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Southbury with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Southbury vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Southbury Holiday Homes essential information

Accommodation
451 Holiday Homes
Lowest Price
AU$155
Highest Price
AU$502
Popular accommodation
Historic Connecticut Home w/ Grill & Spacious Yard, Lakeside luxury: beautiful, relaxing 4 bedroom home, Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake, Stylish & Luxurious 3 BDR Home with Play Station, Business or Weekend escape, Cheerful 4 bedrooms residential house., Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views, Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger, Tranquil Litchfield Connecticut Retreat".

Top trending hotels in Southbury

Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is AU$155 per night from 13 Apr to 14 Apr
AU$155
includes taxes & fees
13 Apr - 14 Apr
Located in Southbury, Wyndham Southbury is a 4-minute drive from Lake Quassapaug and 5 minutes from Southford Falls State Park.
Wyndham Southbury
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

3.5 out of 5
522 Heritage Rd, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is AU$241 per night from 2 Apr to 3 Apr
AU$241
includes taxes & fees
2 Apr - 3 Apr
Located in Southbury, Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection is in the suburbs, a 3-minute drive from Southbury Dog Park and 5 ...
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
The price is AU$218 per night from 20 Apr to 21 Apr
AU$218
includes taxes & fees
20 Apr - 21 Apr
New Haven Hotel is centrally located in New Haven, a 4-minute walk from Shubert Theater and 5 minutes by foot from New Haven Green.
New Haven Hotel
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Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 6 Apr to 7 Apr
AU$156
includes taxes & fees
6 Apr - 7 Apr
With a stay at Clarion Inn in North Haven, you'll be within a 15-minute drive of Yale University and Quinnipiac University.
Clarion Inn
Don't see what you're looking for?
See all available properties in Southbury
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.