Book Holiday Homes in Southport

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Featured Holiday Homes in Southport

Over Sized Colonial on Private Road.

Over Sized Colonial on Private Road.

Pound Ridge NY
Stay at this family-friendly holiday home in Pound Ridge. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Pound Ridge Town Park and Keeler ...
Opens in a new windowOver Sized Colonial on Private Road.
Business or Weekend escape

Business or Weekend escape

Stratford CT
The price is NZ$250 per night from 26 Mar to 27 Mar
NZ$250
26 Mar - 27 Mar
includes taxes & fees
Stay at this holiday home in Stratford. Enjoy a garden, an in-room coffee maker and air conditioning. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowBusiness or Weekend escape
Cozy Ocean Front Retreat with Private Beach!

Cozy Ocean Front Retreat with Private Beach!

Milford CT
Stay at this beach holiday home in Milford. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Walnut Beach and The Coastal Center ...
Opens in a new windowCozy Ocean Front Retreat with Private Beach!
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Adorable Cottage with Water Views, Across the street from Prime & other eateries

Adorable Cottage with Water Views, Across the street from Prime & other eateries

Halesite NY
Stay at this holiday home in Huntington. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Cinema Arts Center and Heckscher ...
Opens in a new windowAdorable Cottage with Water Views, Across the street from Prime & other eateries
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich CT
The price is NZ$497 per night from 20 Mar to 21 Mar
NZ$497
20 Mar - 21 Mar
includes taxes & fees
Stay at this holiday home in Greenwich. Enjoy free Wi-Fi, a garden and an in-room coffee maker. Popular attractions Houston Preserve and Hand & Stone Massage ...
Opens in a new window2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Minutes to Beaches - Home Theater, Couples Retreat

Minutes to Beaches - Home Theater, Couples Retreat

Milford CT
Stay at this holiday home in Milford. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Walnut Beach and The Coastal Center at Milford Point ...
Opens in a new windowMinutes to Beaches - Home Theater, Couples Retreat
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

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

Milford CT
Stay at this beach holiday home in Milford. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Twin Rocks and Bowlero Milford are located ...
Opens in a new windowBeach Front Arts & Crafts House With Gorgeous Views Of The Sound
Cheerful 5 bed Residential house.

Cheerful 5 bed Residential house.

Bridgeport CT
Stay at this holiday home in Bridgeport. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Hartford HealthCare Amphitheater and ...
Opens in a new windowCheerful 5 bed Residential house.
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Stamford CT
The price is NZ$598 per night from 12 Apr to 13 Apr
NZ$598
12 Apr - 13 Apr
includes taxes & fees
Stay at this holiday home in Stamford. Enjoy laundry facilities and air conditioning. Popular attractions Museum of Black World War II History and Atlantic Square ...
Opens in a new windowGem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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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
329 Holiday Homes
Lowest Price
NZ$121
Highest Price
NZ$598
Popular accommodation
Over Sized Colonial on Private Road. , Business or Weekend escape, Cozy Ocean Front Retreat with Private Beach!, Adorable Cottage with Water Views, Across the street from Prime & other eateries, 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich., Minutes to Beaches - Home Theater, Couples Retreat, Beach Front Arts & Crafts House With Gorgeous Views Of The Sound, Cheerful 5 bed Residential house., Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Top trending hotels in Southport

Delamar Southport

Delamar Southport

4 out of 5
275 Old Post Rd Southport CT
The price is NZ$401 per night from 22 Mar to 23 Mar
NZ$401
22 Mar - 23 Mar
includes taxes & fees
Stay at this spa hotel in Southport. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowDelamar Southport
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is NZ$199 per night from 5 Apr to 6 Apr
NZ$199
5 Apr - 6 Apr
includes taxes & fees
Stay at this business-friendly hotel in Milford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowHyatt Place Milford / New Haven
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
The price is NZ$121 per night from 9 Apr to 10 Apr
NZ$121
9 Apr - 10 Apr
includes taxes & fees
Stay at this business-friendly motel in Milford. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Popular attractions Silver Sands State Park and Walnut ...
Opens in a new windowMotel 6 Milford, CT
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Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
The price is NZ$250 per night from 29 Mar to 30 Mar
NZ$250
29 Mar - 30 Mar
includes taxes & fees
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowTrumbull Marriott Shelton
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.