Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

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
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton
Stay at this vacation home in Southampton. Enjoy free WiFi, private pools, and a garden. Popular attractions Southampton Golf Range and Shinnecock Hills Golf ...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Waterfront Beach House

Waterfront Beach House

Clinton
Stay at this vacation home in Clinton. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Clinton Plaza Shopping Center and Clinton Town ...
Waterfront Beach House
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Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court-  WATCH VIDEO!!!

Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!

East Hampton
Book a stay at this golf vacation home in East Hampton. Enjoy private pools, a garden, and tennis courts. Popular attractions LongHouse Reserve and The Jewish ...
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
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
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
Oceanfront Beach House lay in bed and hear the waves, boats , birds

Oceanfront Beach House lay in bed and hear the waves, boats , birds

Waterford
Book a stay at this beach vacation home in Waterford. Enjoy free WiFi, a beach locale, and a water park. Popular attractions New London Ferry Dock and Pleasure ...
Oceanfront Beach House lay in bed and hear the waves, boats , birds
Historic Essex Home w/ Large Yard Near Downtown!

Historic Essex Home w/ Large Yard Near Downtown!

Essex
Stay at this vacation home in Essex. Enjoy a garden, furnished patios, and in-room washers/dryers. Popular attractions Essex Plaza Shopping Center and Essex ...
Historic Essex Home w/ Large Yard Near Downtown!
Quaint Family-sized Home w/private beach — 5 minutes from wineries!

Quaint Family-sized Home w/private beach — 5 minutes from wineries!

Riverhead
Book a stay at this beach vacation home in South Jamesport. Enjoy free WiFi, a private beach, and a water park. Popular attractions Sherwood House Vineyards ...
Quaint Family-sized Home w/private beach — 5 minutes from wineries!
Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated

Greenport
Stay at this vacation home in Greenport. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Greenport Farmers' Market and Railroad Museum ...
Northfork Townhouse- walk to all/ newly renovated
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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
1447 Holiday Homes
Lowest Price
NZ$275
Highest Price
NZ$275
Popular accommodation
Gorgeous private Hamptons house with pool and volleyball court, Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Waterfront Beach House, Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!, Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included, Oceanfront Beach House lay in bed and hear the waves, boats , birds, Historic Essex Home w/ Large Yard Near Downtown!, Quaint Family-sized Home w/private beach — 5 minutes from wineries!, Northfork Townhouse- walk to all/ newly renovated

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$275 per night from 25 Nov to 26 Nov
NZ$275
includes taxes & fees
25 Nov - 26 Nov
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the ...
The Harbor Front Inn
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is NZ$275 per night from 10 Dec to 11 Dec
NZ$275
includes taxes & fees
10 Dec - 11 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
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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Greenporter Hotel

Greenporter Hotel

2 out of 5
326 Front St, Greenport, NY
Stay at this hotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Greenporter Hotel
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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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