Book Holiday Homes in Southold

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Featured Holiday Homes in Southold

10 Bedroom Hampton House with a regulation size Pickleball

10 Bedroom Hampton House with a regulation size Pickleball

Hampton Bays
With a stay at this vacation home in Hampton Bays, you'll be near the beach, within a 5-minute drive of The Hamptons Beaches and Ponquogue Beach.
10 Bedroom Hampton House with a regulation size Pickleball
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

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

Southampton
With a stay at this vacation home in Southampton, you'll be by the sea, within a 5-minute drive of The Hamptons Beaches and North Main Street Historic ...
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Waterfront House with picture-perfect views from all 3 levels.

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

Westbrook
Located in Westbrook (Westbrook Center), this vacation home is within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.
Waterfront House with picture-perfect views from all 3 levels.
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Stunning New Designer Renovation

Stunning New Designer Renovation

Sag Harbor
With a stay at this vacation home in Sag Harbor, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and Oakland Cemetery.
Stunning New Designer Renovation
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

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

Westhampton Beach
With a stay at this vacation home in Westhampton Beach, you'll be by the sea, within a 5-minute drive of The Hamptons Beaches and Westhampton Beach Performing ...
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

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

Hampton Bays
With a stay at this vacation home in Hampton Bays, you'll be on the beach, within a 5-minute drive of The Hamptons Beaches and Meschutt Beach.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton
With a stay at this vacation home in Clinton, you'll be near the beach, just a 4-minute walk from Adam Stanton House and General Store Museum and 12 minutes ...
Large Charming Historic House close to Beaches
Sprawling Southampton Home: Private Pool

Sprawling Southampton Home: Private Pool

Southampton
With a stay at this vacation home in Southampton, you'll be by the sea, within a 5-minute drive of The Hamptons Beaches and Shinnecock Hills Golf Course.
Sprawling Southampton Home: Private Pool
Cozy Westbrook Vacation Rental - Walk to Beach!

Cozy Westbrook Vacation Rental - Walk to Beach!

Westbrook
With a stay at this vacation home in Westbrook (Westbrook Center), you'll be a 1-minute drive from Westbrook Town Beach and 6 minutes from Tanger Outlets.
Cozy Westbrook Vacation Rental - Walk to Beach!
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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.

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
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!

Top trending hotels in Southold

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is AU$347 per night from 13 Apr to 14 Apr
AU$347
includes taxes & fees
13 Apr - 14 Apr
When you stay at The Shoals Suites and Slips in Southold, you'll be near the bay, within a 5-minute drive of The Old Field Vineyards and Mattebella ...
The Shoals Suites and Slips
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$373 per night from 1 Apr to 2 Apr
AU$373
includes taxes & fees
1 Apr - 2 Apr
With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing ...
Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$145 per night from 1 Apr to 2 Apr
AU$145
includes taxes & fees
1 Apr - 2 Apr
Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Crystal Lake Town Park.
Pier Blue Inn Old Saybrook - Essex
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Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is AU$231 per night from 8 Apr to 9 Apr
AU$231
includes taxes & fees
8 Apr - 9 Apr
With a stay at Hyatt Place Long Island East End in Riverhead, you'll be on a river, just a 5-minute walk from Suffolk Theater and 6 minutes by foot from All ...
Hyatt Place Long Island East End
Don't see what you're looking for?
See all available properties in Southold
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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.