Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

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
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!
The Dollhouse is conveniently located. Mystic, Beaches, parks, casinos, shopping

The Dollhouse is conveniently located. Mystic, Beaches, parks, casinos, shopping

Waterford
With a stay at this vacation home in Waterford, you'll be by the sea, within a 10-minute drive of New London Ferry Dock and Amtrak Beach.
The Dollhouse is conveniently located. Mystic, Beaches, parks, casinos, shopping
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.

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

Holiday houses in Greenport 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 Greenport 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 Greenport adventures, obvs.

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

Greenport Holiday Homes essential information

Accommodation
1830 Holiday Homes
Lowest Price
AU$346
Highest Price
AU$507
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, Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!, The Dollhouse is conveniently located. Mystic, Beaches, parks, casinos, shopping, 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 Greenport

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
The price is AU$354 per night from 24 Apr to 25 Apr
AU$354
includes taxes & fees
24 Apr - 25 Apr
When you a stay at The Harbor Front Inn in Greenport, you'll be near the bay, just steps from Camera Obscura and Greenport Carousel.
The Harbor Front Inn
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is AU$507 per night from 5 May to 6 May
AU$507
includes taxes & fees
5 May - 6 May
When you stay at Sound View Greenport in Greenport, you'll be by the ocean, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.
Sound View Greenport
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd, Greenport, NY
The price is AU$349 per night from 23 Apr to 24 Apr
AU$349
includes taxes & fees
23 Apr - 24 Apr
When you stay at Silver Sands Motel & Beach Bungalows in Greenport, you'll be on the waterfront, within a 5-minute drive of Railroad Museum of Long Island and ...
Silver Sands Motel & Beach Bungalows
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Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
The price is AU$346 per night from 7 May to 8 May
AU$346
includes taxes & fees
7 May - 8 May
When you stay at Cliffside Resort Condominiums in Greenport, you'll be near the beach, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.
Cliffside Resort Condominiums
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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.