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
Book a stay at this family-friendly vacation home in Hampton Bays. Enjoy private pools, a water park, and a garden. Popular attractions Ponquogue Beach and Tiana ...
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
Stay at this vacation home in Southampton. Enjoy free WiFi, a garden, and patios. Popular attractions The Hamptons Beaches and Our Lady of Poland Catholic Church ...
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
Book a stay at this beach vacation home in Westbrook. Enjoy free WiFi, a beach locale, and furnished patios. Popular attractions Westbrook Town Beach and Tanger ...
Waterfront House with picture-perfect views from all 3 levels.
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Stunning New Designer Renovation

Stunning New Designer Renovation

Sag Harbor
Book a stay at this business-friendly vacation home in Sag Harbor. Enjoy free WiFi, private pools, and a fitness center. Popular attractions The Hamptons Beaches ...
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
Book a stay at this beach vacation home in Hampton Bays. Enjoy a beach locale, a water park, and a garden. Popular attractions Meschutt Beach and Sebonack Golf ...
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
Stay at this vacation home in Waterford. Enjoy free WiFi, a garden, and patios. Popular attractions Ocean Beach Park and Amtrak Beach are located nearby.
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
Stay at this vacation home in Clinton. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Adam Stanton House and General Store Museum and ...
Large Charming Historic House close to Beaches
Cozy Westbrook Vacation Rental - Walk to Beach!

Cozy Westbrook Vacation Rental - Walk to Beach!

Westbrook
Stay at this vacation home in Westbrook. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Westbrook Town Beach and Tanger ...
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
Book a stay at this beach vacation home in Madison. Enjoy free WiFi, a beach locale, and patios. Popular attractions Chaffinch Island State Park and Henry Whitfield ...
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
NZ$374
Highest Price
NZ$644
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 NZ$374 per night from 27 Apr to 28 Apr
NZ$374
includes taxes & fees
27 Apr - 28 Apr
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, an outdoor pool, and a 24-hour health club. Our guests praise the helpful staff ...
The Harbor Front Inn
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is NZ$644 per night from 21 Apr to 22 Apr
NZ$644
includes taxes & fees
21 Apr - 22 Apr
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
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 NZ$375 per night from 23 Apr to 24 Apr
NZ$375
includes taxes & fees
23 Apr - 24 Apr
Stay at this 4-star beach hotel in Greenport. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions ...
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 NZ$374 per night from 7 May to 8 May
NZ$374
includes taxes & fees
7 May - 8 May
Stay at this 3-star beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
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.