Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

East Lyme
Book a stay at this family-friendly vacation home in East Lyme. Enjoy free WiFi, private pools, and breakfast (surcharge). Our guests praise the helpful staff ...
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Gorgeous private Hamptons house with pool and volleyball court

Gorgeous private Hamptons house with pool and volleyball court

Hampton bays
Stay at this vacation home in Hampton Bays. Enjoy a garden, a pool table, and patios. Popular attractions Meschutt Beach and Tiana Beach are located nearby.
Gorgeous private Hamptons house with pool and volleyball court
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

Hampton Bays
Stay at this vacation home in Hampton Bays. Enjoy free WiFi, private pools, and a water park. Popular attractions Sandbar Beach and Triton Beach are located ...
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
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Charming beach home, complete with pool & cozy guest house!

Charming beach home, complete with pool & cozy guest house!

Clinton
Book a stay at this family-friendly vacation home in Clinton. Enjoy free WiFi, private pools, and a garden. Popular attractions Indian River Marina and Adam ...
Charming beach home, complete with pool & cozy guest house!
Exquisite New Hampton Home in a Perfect Location

Exquisite New Hampton Home in a Perfect Location

East Hampton
Stay at this vacation home in East Hampton. Enjoy private pools, a fitness center, and a garden. Popular attractions Three Mile Harbor and LongHouse Reserve ...
Exquisite New Hampton Home in a Perfect Location
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

Amagansett
Stay at this vacation home in Amagansett. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Amagansett Beach and Atlantic Avenue Beach ...
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

New London
Stay at this vacation home in New London. Enjoy free WiFi, a garden, and a pool table. Popular attractions Ocean Beach Park and New London Harbor Light are located ...
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Clinton
The price is NZ$648 per night from 23 Dec to 24 Dec
NZ$648
includes taxes & fees
23 Dec - 24 Dec
Stay at this vacation home in Clinton. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Clinton Town Beach and Clinton Plaza Shopping ...
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Fall in the🌅beautiful sunsets

Fall in the🌅beautiful sunsets

Hampton Bays
Stay at this vacation home in Hampton Bays. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Tiana Beach and Ponquogue Beach ...
Fall in the🌅beautiful sunsets
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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
1423 Holiday Homes
Lowest Price
NZ$344
Highest Price
NZ$648
Popular accommodation
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Gorgeous private Hamptons house with pool and volleyball court, Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!, Charming beach home, complete with pool & cozy guest house!, Exquisite New Hampton Home in a Perfect Location, COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach, Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!
, Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included, Fall in the🌅beautiful sunsets

Top trending hotels in Greenport

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is NZ$382 per night from 24 Dec to 25 Dec
NZ$382
includes taxes & fees
24 Dec - 25 Dec
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
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
The price is NZ$344 per night from 6 Jan to 7 Jan
NZ$344
includes taxes & fees
6 Jan - 7 Jan 2025
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
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
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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Hotel Moraine

Hotel Moraine

2 out of 5
62005 County Route 48, Greenport, NY
The price is NZ$639 per night from 1 Jan to 2 Jan
NZ$639
includes taxes & fees
1 Jan - 2 Jan 2025
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
Hotel Moraine
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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.