Book Holiday Homes in Greenport

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

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Southampton
Stay at this vacation home in Southampton. Enjoy laundry facilities and air conditioning. Popular attractions Cooper's Beach and The Hamptons Beaches are located ...
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Hamptons Retreat

Hamptons Retreat

Hampton Bays
Stay at this vacation home in Hampton Bays. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Cooper's Beach and Good Ground Park are ...
Hamptons Retreat
Sag Harbor Village Gem

Sag Harbor Village Gem

Sag Harbor
Stay at this vacation home in Sag Harbor. Enjoy free WiFi, laundry facilities, and patios. Popular attractions The Hamptons Beaches and Havens Beach are located ...
Sag Harbor Village Gem
Save an average of 15% on thousands of hotels when you're signed in
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
Stay at this vacation home in East Hampton. Enjoy free WiFi, private pools, and a garden. Popular attractions Pollock-Krasner House and Study Center and Kaplan ...
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Shoreline Oasis

Shoreline Oasis

Clinton
The price is NZ$440 per night from 4 Aug to 5 Aug
NZ$440
4 Aug - 5 Aug
includes taxes & fees
Stay at this vacation home in Clinton. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Hammonasset Beach State Park and Indian ...
Shoreline Oasis
Perfect Mid-Century Private Waterfront East Hampton Retreat!

Perfect Mid-Century Private Waterfront East Hampton Retreat!

East Hampton
Book a stay at this beach vacation home in East Hampton. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Kaplan Meadows Sanctuary and Pollock-Krasner ...
Perfect Mid-Century Private Waterfront East Hampton Retreat!
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
Stay at this vacation home in Amagansett. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Amagansett Beach and Atlantic ...
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

East Hampton
Stay at this vacation home in East Hampton. Enjoy private pools, a garden, and laundry facilities. Popular attractions East Hampton Village Nature Trail and ...
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage
The Cooper-Burke House

The Cooper-Burke House

Sag Harbor
Stay at this vacation home in Sag Harbor. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions The Hamptons Beaches and Sag Harbor Marine Park ...
The Cooper-Burke House
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
1969 Holiday Homes
Lowest Price
NZ$440
Highest Price
NZ$693
Popular accommodation
Charming Two-Story Retreat in Southampton Village walk to town, beach and train., Hamptons Retreat, Sag Harbor Village Gem , Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen, Shoreline Oasis, Perfect Mid-Century Private Waterfront East Hampton Retreat! , Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access, Driftwood Cottage by RoveTravel| 3BR Quiet Cottage, The Cooper-Burke House

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$693 per night from 1 Sept to 2 Sept
NZ$693
1 Sept - 2 Sept
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Sound View Greenport
Greenporter Hotel

Greenporter Hotel

2 out of 5
326 Front St, Greenport, NY
Stay at this hotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Greenporter Hotel
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
The price is NZ$541 per night from 3 Sept to 4 Sept
NZ$541
3 Sept - 4 Sept
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the ...
The Harbor Front Inn
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
Stay at this 4-star beach hotel in Greenport. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions ...
Silver 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.