Book Holiday Homes in Greenport

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Greenport

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
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Jamesport NY
Located in Riverhead, this vacation home is within a 15-minute walk of Terra Vite North Fork Winery & Vineyard and Jason's Vineyard.
Opens in a new windowComfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
Walk to the  beach at Black Point, Niantic, Ct.

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

Niantic CT
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.
Save an average of 15% on thousands of hotels when you're signed in
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
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 NY
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
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Hampton Bays NY
The price is AU$1,739 per night from 11 Feb to 12 Feb
AU$1,739
11 Feb - 12 Feb
includes taxes & fees
With a stay at this vacation home in Hampton Bays, you'll be on the beach, within a 5-minute drive of The Hamptons Beaches and Ponquogue Beach.
Opens in a new windowBlack Swan: Beachfront Home w/ Year-Round Jacuzzi
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Old Lyme CT
Located in Old Lyme, this vacation home is by the ocean, within a 10-minute drive of Lyme Academy of Fine Arts and Rocky Neck State Park.
Opens in a new windowBeachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

East Hampton NY
With a stay at this vacation home in East Hampton, you'll be near the beach, within a 10-minute drive of The Hamptons Beaches and The Jewish Center of the ...
Opens in a new windowCharming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living
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 NY
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.
Opens in a new windowMid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Don't see what you're looking for?
See all available properties in Greenport
View all properties
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$258
Highest Price
AU$1,739
Popular accommodation
Large Charming Historic House close to Beaches, Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!, Walk to the beach at Black Point, Niantic, Ct., Aqua Vista , Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available , Black Swan: Beachfront Home w/ Year-Round Jacuzzi, Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!, Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living, Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

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$280 per night from 12 Mar to 13 Mar
AU$280
12 Mar - 13 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$258 per night from 12 Mar to 13 Mar
AU$258
12 Mar - 13 Mar
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$523 per night from 11 Feb to 12 Feb
AU$523
11 Feb - 12 Feb
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
Save an average of 15% on thousands of hotels when you're signed in
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 ...
Opens in a new windowSilver Sands Motel & Beach Bungalows
Don't see what you're looking for?
See all available properties in Greenport
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.