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

Greenport Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Greenport vacation rentals

Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
$266 nightly
The price is $304
Nov 12 - Nov 13
Total with taxes and fees
Cliffside Resort Condominiums
A beach with people relaxing on chairs and sunbathing.

2. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (27 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
$218 nightly
The price is $249
Nov 2 - Nov 3
Total with taxes and fees
Harbor Heights
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

3. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
$216 nightly
The price is $247
Nov 9 - Nov 10
Total with taxes and fees
Aqua Vista
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

4. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (56 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
$216 nightly
The price is $247
Nov 10 - Nov 11
Total with taxes and fees
The SandPiper
A modern house with a deck, outdoor seating, and a fire pit.

5. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
$268 nightly
The price is $306
Oct 19 - Oct 20
Total with taxes and fees
North Fork Resort
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, (34 reviews)
"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
$328 nightly
The price is $375
Nov 2 - Nov 3
Total with taxes and fees
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.
$268 nightly
The price is $306
Oct 19 - Oct 20
Total with taxes and fees
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, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
$393 nightly
The price is $449
Nov 3 - Nov 4
Total with taxes and fees
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
9.4 out of 10, Exceptional, (8 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.
$499 nightly
The price is $570
Nov 2 - Nov 3
Total with taxes and fees
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
9.6 out of 10, Exceptional, (14 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
$535 nightly
The price is $611
Nov 2 - Nov 3
Total with taxes and fees
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.
$788 nightly
The price is $900
Nov 3 - Nov 4
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

12. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
$934 nightly
The price is $1,067
Nov 4 - Nov 5
Total with taxes and fees
Beachfront Greenport Villa
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

13. 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
$302 nightly
The price is $345
Oct 18 - Oct 19
Total with taxes and fees
American Beech in Greenport - Deluxe King 6
Room

14. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (326 reviews)
"The room was nice but the bed was horrible. They need to replace the bed ASAP. It is so old that the middle of the bed is touching the floor due to it being worn out. Our backs are still hurting. Otherwise it was a nice room."
United States
William
$167 nightly
The price is $190
Oct 19 - Oct 20
Total with taxes and fees
Windward Shores Ocean Resort
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

15. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
$446 nightly
The price is $510
Oct 19 - Oct 20
Total with taxes and fees
Charming Accommodations in the Hamptons
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

16. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (62 reviews)
"We enjoyed our stay"
United States
JM B.
$183 nightly
The price is $207
Oct 21 - Oct 22
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Room

17. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
$166 nightly
The price is $189
Oct 19 - Oct 20
Total with taxes and fees
Driftwood Resort
A dining area with a round table, six chairs, and a chandelier.

18. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
$1,188 nightly
The price is $1,258
Oct 18 - Oct 19
Total with taxes and fees
Year round Jacuzzi - Blackberry East Hampton Home
A stone pier leading to a beach with houses in the background.

19. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (64 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
$241 nightly
The price is $272
Oct 28 - Oct 29
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

20. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
$1,016 nightly
The price is $1,160
Oct 17 - Oct 18
Total with taxes and fees
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
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

Hyatt Place Long Island East End

Hyatt Place Long Island East End

8/10 Good
"Front desk staff provider typical Long Island hospitality… Just rude! You should send your people to the South for training for six months to get that chip off their shoulder."
shaun 3-night trip
Posted 2 hours ago
Hyatt Place Long Island East End

Find out more about Greenport

Everything you need to know about Greenport vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenport vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenport vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenport vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenport. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greenport in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $189 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greenport rentals

At Expedia, we put the best Greenport vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greenport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenport vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Greenport?

Yes, we give you a choice of vacation rentals in Greenport near Greenport Carousel, or you can select a more remote 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 vacation home rentals that Greenport has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental near Greenport is located on the beach and has a balcony, a barbecue grill, and air-conditioning 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 you can cook with friends or family.

How many vacation rentals are there in Greenport?

With 97 Expedia vacation rentals, you're sure 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 vacation rentals like in Greenport?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Greenport. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family getaway.