Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

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

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

Hampton Bays NY
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!
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Riverhead NY
Located in Riverhead, this vacation home is a 2-minute drive from Roanoke Vineyards and 6 minutes from Long Island National Golf Club.
Opens in a new windowSpacious home near Aquarium & heart of wine country Shopping & close to Hamptons
The SandPiper

The SandPiper

Greenport, NY
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
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Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

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

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

Southampton NY
Located in Southampton, this vacation home is within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
Opens in a new windowDelightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Southampton NY
When you stay at this vacation home in Southampton, you'll be by the sea, a 4-minute drive from The Hamptons Beaches and 6 minutes from Cooper's Beach.
Opens in a new windowBeachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️
Serene Hamptons Retreat with Pool, Bocce Court & Private Beach Access

Serene Hamptons Retreat with Pool, Bocce Court & Private Beach Access

East Hampton NY
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.
Opens in a new windowSerene Hamptons Retreat with Pool, Bocce Court & Private Beach Access
2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

East Lyme CT
Located in Niantic, this vacation home is on the waterfront, within a 10-minute drive of Tumbleweeds and Amtrak Beach.
Opens in a new window2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS
Aqua Vista

Aqua Vista

Greenport, NY
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 windowAqua Vista
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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
1701 Holiday Homes
Lowest Price
AU$303
Highest Price
AU$537
Popular accommodation
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!, Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons, The SandPiper , Large Charming Historic House close to Beaches, Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️, Serene Hamptons Retreat with Pool, Bocce Court & Private Beach Access, 2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS, Aqua Vista

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$323 per night from 29 Mar to 30 Mar
AU$323
29 Mar - 30 Mar
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$303 per night from 13 Apr to 14 Apr
AU$303
13 Apr - 14 Apr
includes taxes & fees
When you 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
The price is AU$537 per night from 29 Mar to 30 Mar
AU$537
29 Mar - 30 Mar
includes taxes & fees
When you stay at Zey Hotel in Greenport, you'll be near the beach, just steps from Greenport Harbor Brewing Company and Greenport Farmers' Market.
Opens in a new windowZey Hotel
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Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd Greenport NY
The price is AU$410 per night from 29 Mar to 30 Mar
AU$410
29 Mar - 30 Mar
includes taxes & fees
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 ...
Opens in a new windowSilver 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.

Top Picks

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^Subject to availability and chosen travel dates.