Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 out of 5
Bridgehampton
The price is AU$624 per night from 1 Oct to 2 Oct
AU$624
1 Oct - 2 Oct
includes taxes & fees
With a stay at this vacation home in Bridgehampton, you'll be within a 15-minute walk of Children's Museum of The East End and South Fork Natural History Museum ...
Opens in a new windowCozy Bungalow Available Nearby Bridgehampton and Sag Harbor
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
With a stay at this vacation home in East Lyme, you'll be by the sea, within a 15-minute drive of New London Ferry Dock and White Gate Farm.
Opens in a new windowHistoric Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Out Door Theater Fire Pit Bocce court-  WATCH VIDEO!!!

Out Door Theater Fire Pit Bocce court- WATCH VIDEO!!!

East Hampton
With a stay at this vacation home in East Hampton, you'll be next to a golf course, within a 10-minute drive of The Hamptons Beaches and LongHouse Reserve.
Opens in a new windowOut Door Theater Fire Pit Bocce court- WATCH VIDEO!!!
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Summer getaway

Summer getaway

East Quogue
With a stay at this vacation home in East Quogue, you'll be within a 10-minute drive of The Hamptons Beaches and Quogue Community Hall.
Opens in a new windowSummer getaway
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.
Opens in a new windowNew Madison beach house - Ocean front- Great views- booking Summer 2025
The SandPiper

The SandPiper

Greenport,
With a stay at this vacation home in Greenport (Pipes Cove), you'll be steps from Railroad Museum of Long Island and 3 minutes by foot from East End Seaport ...
Opens in a new windowThe SandPiper
Sea Breeze Paradise: Beachfront & Panoramic Views

Sea Breeze Paradise: Beachfront & Panoramic Views

North Fork
When you stay at this vacation home in Southold, you'll be on the waterfront, within a 5-minute drive of Horton Point Park and Sparkling Pointe.
Opens in a new windowSea Breeze Paradise: Beachfront & Panoramic Views
The Cooper-Burke House

The Cooper-Burke House

Sag Harbor
A stay at this vacation home places you in the heart of Sag Harbor, within a 15-minute walk of The Hamptons Beaches and BookHampton.
Opens in a new windowThe Cooper-Burke House
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Amagansett
With a stay at this vacation home in Amagansett (Beach Hampton), you'll be within a 10-minute walk of The Hamptons Beaches and Amagansett Beach.
Opens in a new windowWalk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
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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
1893 Holiday Homes
Lowest Price
AU$404
Highest Price
AU$624
Popular accommodation
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor , Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Out Door Theater Fire Pit Bocce court- WATCH VIDEO!!!, Summer getaway, New Madison beach house - Ocean front- Great views- booking Summer 2025, The SandPiper , Sea Breeze Paradise: Beachfront & Panoramic Views, The Cooper-Burke House, Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

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$508 per night from 27 Oct to 28 Oct
AU$508
27 Oct - 28 Oct
includes taxes & fees
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.
Opens in a new windowSound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
The price is AU$404 per night from 2 Oct to 3 Oct
AU$404
2 Oct - 3 Oct
includes taxes & fees
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.
Opens in a new windowThe Harbor Front Inn
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street, Greenport, NY
Located in Greenport, Zey Hotel is near the beach, within a 5-minute walk of Greenport Farmers' Market and Greenport Harbor Brewing Company.
Opens in a new windowZey Hotel
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Greenporter Hotel

Greenporter Hotel

2 out of 5
326 Front St, Greenport, NY
With a stay at Greenporter Hotel, you'll be centrally located in Greenport, a 4-minute walk from Greenport Carousel and a 3-minute drive from 67 Steps ...
Opens in a new windowGreenporter 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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