Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 out of 5
Bridgehampton
The price is NZ$955 per night from 19 Oct to 20 Oct
NZ$955
19 Oct - 20 Oct
includes taxes & fees
Stay at this vacation home in Bridgehampton. Enjoy free WiFi, a garden, and patios. Popular attractions The Hamptons Beaches and Channing Daughters Winery are ...
Opens in a new windowCozy Bungalow Available Nearby Bridgehampton and Sag Harbor
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
Book a stay at this family-friendly vacation home in East Lyme. Enjoy free WiFi, private pools, and breakfast (surcharge). Our guests praise the helpful staff ...
Opens in a new windowHistoric Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Out Door Theater Fire Pit Bocce court-  WATCH VIDEO!!!

Out Door Theater Fire Pit Bocce court- WATCH VIDEO!!!

East Hampton
Book a stay at this golf vacation home in East Hampton. Enjoy private pools, a garden, and laundry facilities. Popular attractions The Hamptons Beaches and LongHouse ...
Opens in a new windowOut Door Theater Fire Pit Bocce court- WATCH VIDEO!!!
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Summer getaway

Summer getaway

East Quogue
Book a stay at this family-friendly vacation home in East Quogue. Enjoy private pools, a fitness center, and a garden. Popular attractions Quogue Community Hall ...
Opens in a new windowSummer getaway
New Madison beach house - Ocean front- Great views- booking Summer 2025

New Madison beach house - Ocean front- Great views- booking Summer 2025

Madison
Book a stay at this beach vacation home in Madison. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Chaffinch Island State Park and Henry ...
Opens in a new windowNew Madison beach house - Ocean front- Great views- booking Summer 2025
The SandPiper

The SandPiper

Greenport,
Stay at this vacation home in Greenport. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Railroad Museum of Long Island and East End Seaport ...
Opens in a new windowThe SandPiper
Sea Breeze Paradise: Beachfront & Panoramic Views

Sea Breeze Paradise: Beachfront & Panoramic Views

North Fork
Stay at this vacation home in Southold. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Horton Point Park and The Old Field ...
Opens in a new windowSea Breeze Paradise: Beachfront & Panoramic Views
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 ...
Opens in a new windowThe Cooper-Burke House
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 ...
Opens in a new windowWalk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
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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
1893 Holiday Homes
Lowest Price
NZ$452
Highest Price
NZ$955
Popular accommodation
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor , Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Out Door Theater Fire Pit Bocce court- WATCH VIDEO!!!, Summer getaway, New Madison beach house - Ocean front- Great views- booking Summer 2025, The SandPiper , Sea Breeze Paradise: Beachfront & Panoramic Views, The Cooper-Burke House, Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

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$607 per night from 29 Sept to 30 Sept
NZ$607
29 Sept - 30 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 ...
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$452 per night from 2 Oct to 3 Oct
NZ$452
2 Oct - 3 Oct
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 ...
Opens in a new windowThe Harbor Front Inn
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street, Greenport, NY
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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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 ...
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.