Holiday Rentals Greenport from £69: Find Short-Term Rentals & Holiday Accommodations

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Greenport holiday rentals

A balcony with a view of the ocean, a lawn, and a house in the background.

1. Cliffside Resort Condominiums

Greenport

William

includes taxes & fees

26 Nov - 27 Nov

A beach with people relaxing on chairs and sunbathing.

2. Harbor Heights

Pipes Cove

Steven R.

includes taxes & fees

15 Nov - 16 Nov

A sign on a porch with the text "The Sandpiper" and "Greenport, NY".

3. The SandPiper

Pipes Cove

Manuela C.

includes taxes & fees

30 Nov - 1 Dec

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

4. Aqua Vista

Pipes Cove

Carey D.

includes taxes & fees

18 Nov - 19 Nov

A modern house with a deck, outdoor seating, and a fire pit.

5. North Fork Resort

Greenport

Altynai

includes taxes & fees

15 Nov - 16 Nov

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

Pipes Cove

Callie E.

includes taxes & fees

15 Nov - 16 Nov

An outdoor dining area with hanging lights, palm trees, and a bar.

7. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

includes taxes & fees

15 Nov - 16 Nov

A wooden pathway leading to a beach with scattered rocks and greenery.

8. Beach Block Hideaway

Pipes Cove

Teresa C.

includes taxes & fees

15 Nov - 16 Nov

A modern dining area with a wooden table, white chairs, and a chandelier.

9. Northfork Townhouse walk to all

Greenport

Beth R.

includes taxes & fees

1 Dec - 2 Dec

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

Greenport

Liz H.

includes taxes & fees

22 Nov - 23 Nov

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

Greenport

Jeannette M.

includes taxes & fees

1 Dec - 2 Dec

A wooden deck with two Adirondack chairs and a fire pit, overlooking a beach at sunset.

12. Beachfront Greenport Villa

Greenport

Kate R.

includes taxes & fees

2 Dec - 3 Dec

An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

13. American Beech in Greenport - Deluxe King 6

Greenport

Jeffrey

includes taxes & fees

15 Nov - 16 Nov

14. Windward Shores Ocean Resort

Napeague

Banessa

includes taxes & fees

15 Nov - 16 Nov

A kitchen with a wooden countertop, a black sink, and a window with a view of trees.

15. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

Southold

Kelly V.

includes taxes & fees

24 Nov - 25 Nov

A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

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

Clinton

Marcy C.

includes taxes & fees

19 Nov - 20 Nov

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

17. Charming Accommodations in the Hamptons

Sag Harbor

includes taxes & fees

16 Nov - 17 Nov

A dining area with a round table, six chairs, and a chandelier.

18. Year round Jacuzzi - Blackberry East Hampton Home

East Hampton

Suzanne R.

A beach with footprints leading to the water, a sunset in the background, and a clear sky.

19. Steps to the beach | Seabreeze Cottage #3

Hampton Bays

"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...

Lydia

includes taxes & fees

15 Nov - 16 Nov

A rocky shoreline with a beach and ocean in the background.

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

Old Lyme

"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."

Janine

includes taxes & fees

15 Nov - 16 Nov

View all properties

Find holiday rentals that suit your style

Top Greenport Hotel Reviews

A red door with a 'Gone to the Beach' sign, a wicker chair, a table with a plate of food and drinks, and a potted plant.

The Homestead

Madison Center

10/10 Excellent

Karen

A spacious dining area with multiple tables and chairs, large windows with a marina view, and a modern kitchen with white cabinetry.

Inn at Harbor Hill Marina

Niantic

10/10 Excellent

Claire

A living room with a stone fireplace, grey sofas, and a coffee table.

The Captain Stannard

Westbrook Center

10/10 Excellent

Jessica

An outdoor dining area with trees and tables under string lights.

The 1770 House Restaurant & Inn

East Hampton

10/10 Excellent

Liina

A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.

Westbrook Inn B&B

Westbrook Center

8/10 Good

Nicola

A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.

Canoe Place Inn and Cottages

Hampton Bays

10/10 Excellent

Ann marie

A swimming pool with lounge chairs and umbrellas, surrounded by a paved patio and a mural on the building.

The Bentley Hotel Southampton

Southampton

10/10 Excellent

James

A blue door, a small table with a potted plant, and a green chair on a porch.

Marina Bay Cottages

Waterford

10/10 Excellent

Lorna

A storefront with a sign reading "THE SHOALS".

The Shoals Suites and Slips

Southold

10/10 Excellent

Paul

A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

The Hampton Maid

Hampton Bays

10/10 Excellent

We had a lovely 3 night stay at this beautiful traditional family owned property (2 rooms/cabins). It was a perfect reset after 5 nights spent in NYC, the surroundings were so peaceful and well maintained as were the rooms. Great to see some local wildlife on the grounds at times too. Staff were friendly and helpful, parking is conveniently located beside each room, making it easy for luggage etc. Daily maid service, rooms were immaculately clean. We had breakfast at the property on one of the...

Sharon

Find out more about Greenport

Everything you need to know about Greenport holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenport holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenport holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenport holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenport holiday rentals we have selected for you start as low as £69 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Greenport rentals

At Expedia, we put the best Greenport holiday 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 holiday.

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.

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?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Greenport is located on the beach, and has a balcony, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Greenport?

With 97 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.

Search Holiday Rentals in Greenport

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Greenport holiday rentals

1. Cliffside Resort Condominiums

2. Harbor Heights

3. The SandPiper

4. Aqua Vista

5. North Fork Resort

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

7. American Beech in Greenport - Petite King Room 7

8. Beach Block Hideaway

9. Northfork Townhouse walk to all

10. Renovated Townhouse walk to all

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

12. Beachfront Greenport Villa

13. American Beech in Greenport - Deluxe King 6

14. Windward Shores Ocean Resort

15. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

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

17. Charming Accommodations in the Hamptons

18. Year round Jacuzzi - Blackberry East Hampton Home

19. Steps to the beach | Seabreeze Cottage #3

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

Find holiday rentals that suit your style

Top Greenport Hotel Reviews

The Homestead

10/10 Excellent

Find out more about Greenport

Greenport holiday rentals: An excellent choice for every season

How to find incredible deals on Greenport rentals

Frequently Asked Questions

Can I find a holiday rental in Greenport?

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

How many holiday rentals are there in Greenport?

What can I see and do in Greenport?

What are holiday rentals like in Greenport?