Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

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
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
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12  Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook
The price is AU$1,841 per night from 27 Nov to 28 Nov
AU$1,841
27 Nov - 28 Nov
includes taxes & fees
Located in Old Saybrook, this vacation home is on the waterfront, a 5-minute walk from Chalker Beach and within a 5-minute drive of Crystal Lake Town Park.
Opens in a new windowOceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
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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
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
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor
With a stay at this vacation home in Sagaponack, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and Wolffer Estates Vineyard.
Opens in a new windowGrab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton
With a stay at this vacation home in Clinton, you'll be near the beach, just a 4-minute walk from Adam Stanton House and General Store Museum and 12 minutes ...
Opens in a new windowLarge Charming Historic House close to Beaches
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays
When you stay at this vacation home in Hampton Bays, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
Opens in a new windowBeautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Walk to the  beach at Black Point, Niantic, Ct.

Walk to the beach at Black Point, Niantic, Ct.

Niantic
When you stay at this vacation home in Niantic, you'll be near the beach and within a 5-minute drive of Attawan Beach.
Opens in a new windowWalk to the beach at Black Point, Niantic, Ct.
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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
1767 Holiday Homes
Lowest Price
AU$313
Highest Price
AU$1,841
Popular accommodation
The SandPiper , Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included, Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access, The Cooper-Burke House, Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available , Large Charming Historic House close to Beaches, Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!, Walk to the beach at Black Point, Niantic, Ct.

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$418 per night from 10 Dec to 11 Dec
AU$418
10 Dec - 11 Dec
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$313 per night from 10 Dec to 11 Dec
AU$313
10 Dec - 11 Dec
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
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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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.
Opens in a new windowCliffside 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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^Subject to availability and chosen travel dates.