Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Southampton
With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Cooper's Beach.
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Hamptons Retreat

Hamptons Retreat

Hampton Bays
With a stay at this vacation home in Hampton Bays, you'll be within a 10-minute drive of The Hamptons Beaches and Good Ground Park.
Hamptons Retreat
Sag Harbor Village Gem

Sag Harbor Village Gem

Sag Harbor
With a stay at this vacation home in Sag Harbor, you'll be within a 10-minute walk of The Hamptons Beaches and Havens Beach.
Sag Harbor Village Gem
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Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

East Hampton
With a stay at this vacation home, you'll be centrally located in East Hampton, within a 5-minute drive of The Hamptons Beaches and Three Mile Harbor.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Shoreline Oasis

Shoreline Oasis

Clinton
The price is AU$407 per night from 6 Aug to 7 Aug
AU$407
6 Aug - 7 Aug
includes taxes & fees
A stay at this vacation home places you in the heart of Clinton, within a 15-minute walk of Indian River Marina and Adam Stanton House and General Store ...
Shoreline Oasis
Perfect Mid-Century Private Waterfront East Hampton Retreat!

Perfect Mid-Century Private Waterfront East Hampton Retreat!

East Hampton
With a stay at this vacation home in East Hampton (Clearwater Beach), you'll be within a 5-minute drive of The Hamptons Beaches and Three Mile Harbor.
Perfect Mid-Century Private Waterfront East Hampton Retreat!
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.
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

East Hampton
With a stay at this vacation home in East Hampton (East Hampton North), you'll be within a 5-minute drive of The Hamptons Beaches and First United Methodist ...
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage
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 Sag Harbor Marine Park.
The Cooper-Burke House
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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
1969 Holiday Homes
Lowest Price
AU$407
Highest Price
AU$633
Popular accommodation
Charming Two-Story Retreat in Southampton Village walk to town, beach and train., Hamptons Retreat, Sag Harbor Village Gem , Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen, Shoreline Oasis, Perfect Mid-Century Private Waterfront East Hampton Retreat! , Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access, Driftwood Cottage by RoveTravel| 3BR Quiet Cottage, The Cooper-Burke House

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$633 per night from 1 Sept to 2 Sept
AU$633
1 Sept - 2 Sept
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.
Sound View Greenport
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 ...
Greenporter Hotel
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
The price is AU$509 per night from 1 Sept to 2 Sept
AU$509
1 Sept - 2 Sept
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.
The Harbor Front Inn
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Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd, Greenport, NY
When you stay at Silver Sands Motel & Beach Bungalows in Greenport, you'll be on the waterfront, within a 5-minute drive of Railroad Museum of Long Island and ...
Silver Sands Motel & Beach Bungalows
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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.