Book Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

Enjoy Autumn with us.

Enjoy Autumn with us.

Southold
Stay at this vacation home in Southold. Enjoy free WiFi, a garden, and patios. Popular attractions The Old Field Vineyards and Sparkling Pointe are located ...
Enjoy Autumn with us.
Beautiful Private 4 BR, Heated Pool. Close to Everything.

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

East Hampton
Book a stay at this family-friendly vacation home in East Hampton. Enjoy private pools, a garden, and patios. Popular attractions Three Mile Harbor and Pollock-Krasner ...
Beautiful Private 4 BR, Heated Pool. Close to Everything.
Cozy Westbrook Vacation Rental - Walk to Beach!

Cozy Westbrook Vacation Rental - Walk to Beach!

Westbrook
Stay at this vacation home in Westbrook. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Westbrook Town Beach and Tanger ...
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
Stay at this vacation home in East Hampton. Enjoy private pools, a fitness center, and a garden. Popular attractions East Hampton Historical Society and Hither ...
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
Stay at this vacation home in Amagansett. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Amagansett Beach and Atlantic Avenue 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
Stay at this vacation home in Southampton. Enjoy free WiFi, private pools, and a garden. Popular attractions Southampton Golf Range and Shinnecock Hills Golf ...
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
Stay at this vacation home in New London. Enjoy free WiFi, a garden, and a pool table. Popular attractions Ocean Beach Park and New London Harbor Light are located ...
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
Book a stay at this beach vacation home in East Hampton. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Pollock-Krasner House and Study ...
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
Book a stay at this family-friendly vacation home in Waterford. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Crystal Mall and Amtrak ...
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
NZ$339
Highest Price
NZ$425
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 NZ$376 per night from 9 Mar to 10 Mar
NZ$376
includes taxes & fees
9 Mar - 10 Mar
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
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
The price is NZ$339 per night from 9 Mar to 10 Mar
NZ$339
includes taxes & fees
9 Mar - 10 Mar
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, an outdoor pool, and a 24-hour health club. Our guests praise the helpful staff ...
The Harbor Front Inn
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
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American Beech Hotel

American Beech Hotel

3.5 out of 5
300 Main Street, Greenport, NY
The price is NZ$425 per night from 9 Mar to 10 Mar
NZ$425
includes taxes & fees
9 Mar - 10 Mar
Stay at this 3.5-star inn in Greenport. Enjoy free breakfast, free bicycles on site, and daily housekeeping. Our guests praise the helpful staff in our reviews. ...
American Beech 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.