An aerial view of a harbor with boats, a ship, and a dock extending into the water.

Greenport Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Greenport holiday rentals

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (290 reviews)
"Great place!"
United States
Christine
The price is HK$2,288
HK$3,313 total
includes taxes & fees
27 Sept - 28 Sept
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (53 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is HK$2,519
HK$2,878 total
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort
A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (23 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is HK$1,137
HK$2,490 total
includes taxes & fees
5 Oct - 6 Oct
Harbor Heights
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (44 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is HK$1,529
HK$3,019 total
includes taxes & fees
8 Sept - 9 Sept
Aqua Vista
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

5. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
The price is HK$1,376
HK$2,826 total
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
A beach with people relaxing, a pier extending into the water, and a clear sky.

6. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (30 reviews)
"We had a great stay!! "
United States
Callie E.
The price is HK$1,376
HK$3,337 total
includes taxes & fees
15 Sept - 16 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
An outdoor dining area with hanging lights, palm trees, and a bar.

7. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is HK$1,874
HK$2,804 total
includes taxes & fees
21 Sept - 22 Sept
American Beech in Greenport - Petite King Room 7
A wooden pathway leading to a beach with scattered rocks and greenery.

8. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is HK$1,529
HK$3,278 total
includes taxes & fees
7 Sept - 8 Sept
Beach Block Hideaway
A modern dining area with a wooden table, white chairs, and a chandelier.

9. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (7 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is HK$3,881
HK$6,906 total
includes taxes & fees
10 Sept - 11 Sept
Northfork Townhouse walk to all
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

10. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (13 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
The price is HK$2,822
HK$5,518 total
includes taxes & fees
17 Sept - 18 Sept
Renovated Townhouse walk to all
A modern living room with a sofa, coffee table, and dining area.

11. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is HK$4,265
HK$7,613 total
includes taxes & fees
30 Sept - 1 Oct
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

12. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is HK$2,344
HK$3,422 total
includes taxes & fees
17 Sept - 18 Sept
American Beech in Greenport - Deluxe King 6
A campground with several tents and trees, a grassy area, and a view of the water.

13. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (4 reviews)
"great"
United States
Fiona B.
The price is HK$1,516
HK$2,431 total
includes taxes & fees
7 Sept - 8 Sept
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
A small building with a sign reading "General Store Cedar Point Snack Bar."

14. Safari Tent Glamping,S9-CedarPt, East Hampton, NY

Safari Tent Glamping,S9-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"It was relaxing and beautiful - a perfect and affordable getaway from the city! Also great proximity to so many fun things."
United States
Carolyn
The price is HK$1,685
HK$2,552 total
includes taxes & fees
8 Sept - 9 Sept
Safari Tent Glamping,S9-CedarPt, East Hampton, NY

15. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is HK$1,685
HK$2,552 total
includes taxes & fees
8 Sept - 9 Sept
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
A rocky shoreline with a beach and ocean in the background.

16. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.0 out of 10, Very good, (5 reviews)
"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."
United States
Janine
The price is HK$1,172
HK$2,262 total
includes taxes & fees
14 Sept - 15 Sept
The Stern at Soundview · Beach+Ocean+Sunrise

17. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (322 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is HK$1,219
HK$1,606 total
includes taxes & fees
4 Oct - 5 Oct
Windward Shores Ocean Resort
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

18. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$988
HK$1,856 total
includes taxes & fees
28 Sept - 29 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

19. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is HK$1,411
HK$2,581 total
includes taxes & fees
8 Sept - 9 Sept
The gardners Cottage 1 mile from long Island Sound - pet friendly

20. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (248 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is HK$1,283
HK$1,721 total
includes taxes & fees
5 Oct - 6 Oct
Driftwood Resort
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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Top Greenport Hotel Reviews

Aqua Vista

Aqua Vista

10/10 Excellent
"I have never written this before but the pictures you see do not do this property justice. I just loved this apartment. It had all the essentials. Hoping to stay again in the future. Our favorite part was how close it was to the beautiful beach."
Jacqueline 2-night trip
Posted 1 hour ago
Aqua Vista

Find out more about Greenport

Search for holiday rentals in Greenport on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenport using one of the methods below:

  • View our selection of featured holiday rentals in Greenport
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  • Enter your travel dates to view the best deals on holiday rentals in Greenport while they last

Look no further and take a look at our great range of rental properties in Greenport!

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?

Aqua Vista : This highly rated holiday home rental in Greenport is located on the waterfront, and offers a balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Greenport?

With 96 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 East End Seaport Maritime Museum and Railroad Museum of Long Island. 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.