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
Located in Hampton Bays, this vacation home is a 4-minute drive from The Hamptons Beaches and 10 minutes from Meschutt Beach.
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
With a stay at this vacation home in Southampton, you'll be within a 5-minute drive of Southampton Golf Range and North Main Street Historic District.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Waterfront Beach House

Waterfront Beach House

Clinton
Located in Clinton, this vacation home is by the ocean, within a 5-minute drive of Clinton Plaza Shopping Center and Adam Stanton House and General Store ...
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
When you stay at this vacation home in East Hampton, you'll be next to a golf course, within a 5-minute drive of Guild Hall and LongHouse Reserve.
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
When you stay at this vacation home in Clinton, you'll be near the beach and 11 minutes by foot from Clinton Town Beach.
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
Located in Waterford, this vacation home is on the beach, a 2-minute walk from Pleasure Beach and within a 5-minute drive of Harkness Memorial State Park.
Oceanfront Beach House lay in bed and hear the waves, boats , birds
Amazing Home near Ocean Beach

Amazing Home near Ocean Beach

New London
The price is AU$2,042 per night from 6 Nov to 7 Nov
AU$2,042
includes taxes & fees
6 Nov - 7 Nov
When you stay at this vacation home in New London, you'll be next to a golf course, within a 15-minute walk of New London Harbor Light and Ocean Beach Park.
Amazing Home near Ocean Beach
Historic Essex Home w/ Large Yard Near Downtown!

Historic Essex Home w/ Large Yard Near Downtown!

Essex
With a stay at this vacation home in Essex, you'll be a 4-minute walk from Connecticut Valley Railroad State Park and 6 minutes by foot from Essex Steam ...
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
A stay at this vacation home places you in the heart of South Jamesport, within a 5-minute drive of Sherwood House Vineyards and Jason's Vineyard.
Quaint Family-sized Home w/private beach — 5 minutes from wineries!
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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
1466 Holiday Homes
Lowest Price
AU$305
Highest Price
AU$2,042
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, Amazing Home near Ocean Beach, Historic Essex Home w/ Large Yard Near Downtown!, Quaint Family-sized Home w/private beach — 5 minutes from wineries!

Top trending hotels in Greenport

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is AU$305 per night from 1 Dec to 2 Dec
AU$305
includes taxes & fees
1 Dec - 2 Dec
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
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
The price is AU$322 per night from 12 Nov to 13 Nov
AU$322
includes taxes & fees
12 Nov - 13 Nov
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
Greenporter Hotel

Greenporter Hotel

2 out of 5
326 Front St, Greenport, NY
A stay at Greenporter Hotel places you in the heart of Greenport, within a 5-minute walk of Railroad Museum of Long Island and Camera Obscura.
Greenporter Hotel
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Cliffside Resort Condominiums

Cliffside Resort Condominiums

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