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Top Holiday Rentals in Greenport

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (223)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
Cliffside Resort Condominiums

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (285)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is £242
includes taxes & fees
29 Jun - 30 Jun
Windward Shores Ocean Resort

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (224)
"The staff was very friendly I will definitely be back again 👍"
The price is £212
includes taxes & fees
26 Jun - 27 Jun
Driftwood Resort

Canoe Place Waterfront Residences

4.0 star property
The price is £1,686
includes taxes & fees
26 Jun - 27 Jun
Canoe Place Waterfront Residences

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (107)
"Just amazing!"
Rustic Lakeside Cabin at White Gate Farm

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (67)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

10.0 out of 10, Exceptional, (34)
"My wife and I loved our weekend stay at this cabin!"
The price is £563
includes taxes & fees
26 Jun - 27 Jun
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

10.0 out of 10, Exceptional, (83)
"Great time"
Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton

Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is £195
includes taxes & fees
26 Jun - 27 Jun
Shoreline Oasis

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (114)
"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."
Lovely North Fork Beach Cottage (2 BR/2 bath)!

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is £164
includes taxes & fees
2 Jul - 3 Jul
Freeboard at Soundview · Beach+Ocean+Sunrise

East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

10.0 out of 10, Exceptional, (75)
"Stayed here over Thanksgiving. Beautiful house, well appointed, great location. The Hamptons at Thanksgiving are very vibrant. Highly recommend a stay here. "
East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

Southampton cozy cottage by the beach

The price is £439
includes taxes & fees
26 Jun - 27 Jun
Southampton cozy cottage by the beach

Charming East Hampton Home, private yard with fenced in pool, perfect for...

Charming East Hampton Home, private yard with fenced in pool, perfect for...

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (87)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday

9.6 out of 10, Exceptional, (44)
"A lovely beach cottage with bay views and easy walking access to the Atlantic beaches.The place was cozy and clean with expansive open views across reserve land to the bay.A bit tricky to find off the highway at night but we eventually got our bearings!"
Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday

Stunning Southampton Village Modern Home

The price is £12,673
includes taxes & fees
28 Jun - 29 Jun
Stunning Southampton Village Modern Home

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.0 out of 10, Wonderful, (2)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
The price is £192
includes taxes & fees
2 Jul - 3 Jul
The Mast at Soundview · Beach+Ocean+Sunrise
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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Frequently asked questions

Can I find a holiday rental in Greenport?

Yes, there are holiday rentals in Greenport close to Greenport Carousel, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Greenport. Make sure you have time to check out the waterfront and festivals during your trip.

What are some of the best holiday rentals that Greenport has to offer?

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen: This holiday home rental outside of Greenport is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Greenport?

With 113 Expedia holiday rentals, you're guaranteed to find just the right place for your Greenport stay.

What can I see and do in Greenport?

Enjoy the outdoors at 67 Steps Beach and Norman E. Klipp Marine Park, or simply take in cultural attractions like Railroad Museum of Long Island and East End Seaport Maritime Museum. While here, Greenport Carousel and Kontokosta Winery are other places worth a visit.

What are holiday rentals like in Greenport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenport. Holiday rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.