Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

Enjoy Autumn with us.

Enjoy Autumn with us.

Southold
Located in Southold, this vacation home is by the sea, within a 5-minute drive of The Old Field Vineyards and Sparkling Pointe.
Enjoy Autumn with us.
Beautiful Private 4 BR, Heated Pool. Close to Everything.

Beautiful Private 4 BR, Heated Pool. Close to Everything.

East Hampton
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 Three Mile Harbor.
Beautiful Private 4 BR, Heated Pool. Close to Everything.
Cozy Westbrook Vacation Rental - Walk to Beach!

Cozy Westbrook Vacation Rental - Walk to Beach!

Westbrook
With a stay at this vacation home in Westbrook (Westbrook Center), you'll be a 1-minute drive from Westbrook Town Beach and 6 minutes from Tanger Outlets.
Cozy Westbrook Vacation Rental - Walk to Beach!
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Village Fringe Available May 24th - October 31st. Family/Pet Friendly

Village Fringe Available May 24th - October 31st. Family/Pet Friendly

East Hampton
With a stay at this vacation home in East Hampton (East Hampton North), you'll be within a 5-minute drive of The Hamptons Beaches and Hither Hills State ...
Village Fringe Available May 24th - October 31st. Family/Pet Friendly
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

Amagansett
With a stay at this vacation home in Amagansett (Beach Hampton), you'll be steps from The Hamptons Beaches and 14 minutes by foot from Amagansett Beach.
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton
With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Southampton Golf Range.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

New London
When you stay at this vacation home in New London, you'll be by the sea, within a 10-minute walk of Ocean Beach Park and Waterford Beach Park.
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

East Hampton
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.
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+

Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+

Waterford
With a stay at this vacation home in Waterford, you'll be within a 10-minute drive of Amtrak Beach and Hempstead Houses.
Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+
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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
1420 Holiday Homes
Lowest Price
AU$320
Highest Price
AU$386
Popular accommodation
Enjoy Autumn with us., Beautiful Private 4 BR, Heated Pool. Close to Everything., Cozy Westbrook Vacation Rental - Walk to Beach!, Village Fringe Available May 24th - October 31st. Family/Pet Friendly, COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach, Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!
, Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!, Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+

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$360 per night from 17 Feb to 18 Feb
AU$360
includes taxes & fees
17 Feb - 18 Feb
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.
Sound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
The price is AU$320 per night from 17 Feb to 18 Feb
AU$320
includes taxes & fees
17 Feb - 18 Feb
When you a stay at The Harbor Front Inn in Greenport, you'll be near the bay, just steps from Camera Obscura and Greenport Carousel.
The Harbor Front Inn
American Beech Hotel

American Beech Hotel

3.5 out of 5
300 Main Street, Greenport, NY
The price is AU$385 per night from 17 Feb to 18 Feb
AU$385
includes taxes & fees
17 Feb - 18 Feb
When you stay at American Beech Hotel in Greenport, you'll be in the historical district, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.
American Beech Hotel
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Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd, Greenport, NY
The price is AU$386 per night from 20 Feb to 21 Feb
AU$386
includes taxes & fees
20 Feb - 21 Feb
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 ...
Silver Sands Motel & Beach Bungalows
Don't see what you're looking for?
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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.