Book Holiday Homes in Southport

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Featured Holiday Homes in Southport

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
Business or Weekend escape

Business or Weekend escape

Stratford
The price is AU$227 per night from 7 Apr to 8 Apr
AU$227
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
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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.
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Stamford
With a stay at this vacation home in Stamford (North Stamford), you'll be within a 10-minute drive of Yale New Haven Health Long Ridge Medical Center and Hoyt ...
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

Westport
Located in Westport, this vacation home is within a 5-minute drive of Westport Historical Society and Levitt Pavilion.
Main Street Westport, walk to shops, dining, downtown
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Milford
With a stay at this vacation home in Milford, you'll be by the sea, a 3-minute walk from The Coastal Center at Milford Point and a 5-minute drive from Silver ...
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Milford
When you stay at this vacation home in Milford, you'll be on the beach, within a 15-minute drive of Yale University and Yale-New Haven Hospital.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Over Sized Colonial on Private Road.

Over Sized Colonial on Private Road.

Pound Ridge
Located in Pound Ridge, this vacation home is within a 15-minute drive of Pound Ridge Town Park and New Canaan Town Hall.
Over Sized Colonial on Private Road.
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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.

Southport 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 Southport vacation homes are the perfect way for you to wing it.

Holiday houses in Southport 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 Southport 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 Southport adventures, obvs.

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

Southport Holiday Homes essential information

Accommodation
332 Holiday Homes
Lowest Price
AU$167
Highest Price
AU$606
Popular accommodation
Historic Connecticut Home w/ Grill & Spacious Yard, Lakeside luxury: beautiful, relaxing 4 bedroom home, Business or Weekend escape, Cheerful 4 bedrooms residential house., Bright Stylish Chic 4BR 4BA Home Pet Friendly!, Main Street Westport, walk to shops, dining, downtown, BREATHTAKING BUNGALOW-HOME AWAY FROM HOME, Beach Front Arts & Crafts House With Gorgeous Views Of The Sound, Over Sized Colonial on Private Road.

Top trending hotels in Southport

Delamar Southport

Delamar Southport

4 out of 5
275 Old Post Rd, Southport, CT
The price is AU$606 per night from 27 Apr to 28 Apr
AU$606
includes taxes & fees
27 Apr - 28 Apr
Located in Southport, Delamar Southport is by the ocean, within a 5-minute drive of Fairfield Theater Company and Southport Beach.
Delamar Southport
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 12 Apr to 13 Apr
AU$167
includes taxes & fees
12 Apr - 13 Apr
Located in Stamford (Downtown Stamford), Amsterdam Hotel is within a 15-minute walk of Stamford Town Center and Stamford Public Library - Ferguson Library.
Amsterdam Hotel
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is AU$188 per night from 13 Apr to 14 Apr
AU$188
includes taxes & fees
13 Apr - 14 Apr
Located in Norwalk, EVEN Hotel Norwalk by IHG is in the business district, within a 5-minute drive of Gateway Shopping Center and Waveny Park.
EVEN Hotel Norwalk by IHG
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Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue, Old Greenwich, CT
Fully refundableReserve now, pay when you stay
The price is AU$318 per night from 20 Apr to 21 Apr
AU$318
includes taxes & fees
20 Apr - 21 Apr
Located in Old Greenwich, Hyatt Regency Greenwich is by the sea, a 2-minute drive from E. Gaynor Brennan Golf Course and 5 minutes from Bruce Museum of Arts ...
Hyatt Regency Greenwich
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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.