Book Holiday Homes in Southold
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Featured Holiday Homes in Southold

10 Bedroom Hampton House with a regulation size Pickleball

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Waterfront House with picture-perfect views from all 3 levels.

Stunning New Designer Renovation

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Large Charming Historic House close to Beaches

Sprawling Southampton Home: Private Pool

Cozy Westbrook Vacation Rental - Walk to Beach!
Southold 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 Southold vacation homes are the perfect way for you to wing it.
Holiday houses in Southold 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 Southold 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 Southold adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Southold 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 Southold 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.
Southold Holiday Homes essential information
Accommodation | 1861 Holiday Homes |
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Lowest Price | AU$145 |
Highest Price | AU$373 |
Popular accommodation | 10 Bedroom Hampton House with a regulation size Pickleball, Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖 , Waterfront House with picture-perfect views from all 3 levels., Stunning New Designer Renovation, WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr, Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!, Large Charming Historic House close to Beaches, Sprawling Southampton Home: Private Pool, Cozy Westbrook Vacation Rental - Walk to Beach! |
Holiday Homes in Southold
Top Locations for Holiday Homes in Southold
Top trending hotels in Southold

The Shoals Suites and Slips

Water's Edge Resort & Spa

Pier Blue Inn Old Saybrook - Essex

Hyatt Place Long Island East End
More ways to explore Southold
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.