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
When you stay at this vacation home in Southampton, you'll be by the sea, a 4-minute drive from The Hamptons Beaches and 6 minutes from Cooper's Beach.
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
The price is AU$985 per night from 27 Apr to 28 Apr
AU$985
includes taxes & fees
27 Apr - 28 Apr
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
When you stay at this vacation home in Hampton Bays, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Cooper's 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
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!
New Madison beach house - Ocean front- Great views- booking Summer 2025

New Madison beach house - Ocean front- Great views- booking Summer 2025

Madison
Located in Madison, this vacation home is by the ocean, within a 10-minute drive of Deacon John Grave House and Anna Mia's.
New Madison beach house - Ocean front- Great views- booking Summer 2025
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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$142
Highest Price
AU$985
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, Cozy Westbrook Vacation Rental - Walk to Beach!, New Madison beach house - Ocean front- Great views- booking Summer 2025

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$340 per night from 6 May to 7 May
AU$340
includes taxes & fees
6 May - 7 May
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
North Fork 7 Bedroom Farmhouse Escape

North Fork 7 Bedroom Farmhouse Escape

3 out of 5
Southold
When you stay at this vacation home in Southold, you'll be near the beach, within a 5-minute drive of Sparkling Pointe and The Old Field Vineyards.
North Fork 7 Bedroom Farmhouse Escape
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
The price is AU$330 per night from 6 May to 7 May
AU$330
includes taxes & fees
6 May - 7 May
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
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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$142 per night from 25 Apr to 26 Apr
AU$142
includes taxes & fees
25 Apr - 26 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
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.