Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton CT
Stay at this holiday home in Clinton. Enjoy a garden, laundry facilities and patios. Popular attractions Adam Stanton House and General Store Museum and Indian ...
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
Stay at this holiday home in Riverhead. Enjoy laundry facilities, patios and in-room jetted baths. Popular attractions Terra Vite North Fork Winery & 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
Stay at this family-friendly holiday home in Niantic. Enjoy free Wi-Fi, laundry facilities and tennis courts. Popular attractions Attawan Beach and Giants Neck ...
Opens in a new windowWalk to the beach at Black Point, Niantic, Ct.
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Aqua Vista

Aqua Vista

Greenport, NY
Stay at this holiday home in Greenport. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Railroad Museum of Long Island and 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
Stay at this family-friendly holiday home in Sagaponack. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. ...
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
Stay at this beach holiday home in Hampton Bays. Enjoy a beach locale, a garden and laundry facilities. Popular attractions Ponquogue Beach and Tiana Beach are ...
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
Stay at this beach holiday home in Old Lyme. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Lyme Academy of Fine Arts and Rocky ...
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
Stay at this holiday home in East Hampton. Enjoy an in-room coffee maker, in-room fireplaces and air conditioning. Popular attractions Georgica Beach and 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
Stay at this holiday home in East Hampton. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Pollock-Krasner House and Study Center and Kaplan ...
Opens in a new windowMid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
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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
NZ$314
Highest Price
NZ$617
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 NZ$331 per night from 9 Mar to 10 Mar
NZ$331
9 Mar - 10 Mar
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
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 NZ$314 per night from 19 Feb to 20 Feb
NZ$314
19 Feb - 20 Feb
includes taxes & fees
Stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
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 NZ$617 per night from 8 Feb to 9 Feb
NZ$617
8 Feb - 9 Feb
includes taxes & fees
Stay at this 3.5-star boutique hotel in Greenport. Enjoy free parking, free bicycles on-site and daily housekeeping. Popular attractions Greenport Harbor Brewing ...
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
Stay at this beach hotel in Greenport. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the helpful staff in their reviews. Popular attractions ...
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.

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^Subject to availability and chosen travel dates.