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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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 CT
Stay at this family-friendly holiday home in East Lyme. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Our guests praise the helpful staff in their ...
Opens in a new windowHistoric Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
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
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 NY
Stay at this holiday home in Amagansett. Enjoy laundry facilities, in-room fireplaces and air conditioning. Popular attractions Amagansett Beach and Atlantic ...
Opens in a new windowWalk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
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
The price is NZ$2,211 per night from 22 Jan to 23 Jan
NZ$2,211
22 Jan - 23 Jan 2026
includes taxes & fees
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!
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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$351
Highest Price
NZ$2,211
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., Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Aqua Vista , Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access, 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!

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$401 per night from 23 Dec to 24 Dec
NZ$401
23 Dec - 24 Dec
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$351 per night from 23 Dec to 24 Dec
NZ$351
23 Dec - 24 Dec
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
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Stay at this beach aparthotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and East End ...
Opens in a new windowCliffside Resort Condominiums
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Greenporter Hotel

Greenporter Hotel

2 out of 5
326 Front St Greenport NY
Stay at this hotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowGreenporter Hotel
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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.