Greenport Holiday Rentals, New York: Private House Rentals

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Greenport

Pet friendly

Spa

Pool

Apartment

Hot tub

Condo

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Greenport hotels

A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

A kitchen counter with a bottle of wine, a glass, and a basket of snacks.

A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.

A bar area with wooden bar stools and a bookshelf.

1. The Harbor Front Inn

Greenport

Antrii

4.073.895 ₫

5.393.159 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

A modern living room with a grey sofa, black and white patterned rug, and a coffee table.

A modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.

2. The Menhaden

Greenport

Daniel

8.507.327 ₫

10.754.306 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a balcony, outdoor seating area, and a variety of plants.

A bar area with stools, a shelf with glasses, and decorative plants.

A bathroom with a bathtub, green tiled walls, and windows with white blinds.

A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.

3. Zey Hotel

Greenport

Renee

4.714.078 ₫

5.385.835 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A metal chair with a spiral design, surrounded by tall grass and a blurred background of a house and greenery.

A lakeside patio with outdoor seating and a view of the water.

A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.

4. Silver Sands Motel & Beach Bungalows

Greenport

Keith

7.242.480 ₫

8.274.533 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A spacious room with wicker furniture, large windows, and a view of the sea.

A beach bar with wooden chairs and a small table, overlooking the sea.

A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

A coastal building with large windows, a deck, and a view of the sea at sunset.

5. Sound View Greenport

Greenport

Christine

4.481.284 ₫

5.858.600 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

An outdoor dining area with tables and chairs, string lights, and hanging lanterns.

A modern lounge area with a curved sofa, round coffee tables, and a large potted plant.

A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

6. American Beech Hotel

Greenport

Mary

6.487.193 ₫

8.446.025 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

A dining area with a round table, chairs, a vase, and a painting on the wall.

A modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.

A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

7. Oyster Estate

Greenport

Allison

5.819.850 ₫

7.332.817 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A tented accommodation with a bed, television, and a small table with a chair.

A modern living room with a sofa, a dining table, and a kitchen area in the background.

A modern kitchen with a stainless steel sink, white cabinets, and a blue-tiled backsplash.

8. North Fork Resort

Greenport

Altynai

8.310.746 ₫

9.495.027 ₫ total

includes taxes & fees

25 Oct - 26 Oct

9. Cliffside Resort Condominiums

Greenport

William

4.371.871 ₫

7.864.557 ₫ total

includes taxes & fees

12 Nov - 13 Nov

An outdoor patio area with string lights, tables, chairs, and a fire pit.

A large, white building with multiple windows and a prominent tree in the foreground.

A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.

A staircase with wooden balusters and a white wall.

10. The Chequit

The Heights

Patrick

4.632.601 ₫

5.292.747 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.

11. The Shoals Suites and Slips

Southold

Masayo

4.797.885 ₫

6.128.235 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A serene landscape with a calm body of water reflecting trees with autumn foliage.

A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.

A sign for 'House on Chase Creek' with a duck illustration.

12. House on Chase Creek

The Heights

Tracey

4.781.589 ₫

5.462.899 ₫ total

includes taxes & fees

2 Nov - 3 Nov

13. Shelter Island House

Shelter Island Heights

Dorothy

5.205.533 ₫

5.947.111 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A waterfront property with a large house, multiple boats docked, and lush greenery.

A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

A hotel lobby with a sofa, chairs, tables, and a large window.

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

14. Sag Harbor Inn

Sag Harbor

Terri

5.664.654 ₫

6.471.868 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.

A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.

15. Water's Edge Resort & Spa

Westbrook Center

Laurie

4.865.395 ₫

6.041.393 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A marina with boats docked, a fire pit table, and outdoor seating.

An indoor swimming pool with clear blue water, wooden beams, and lounge chairs.

An aerial view of a marina with boats docked, a parking lot, and buildings with a waterfront view.

16. Saybrook Point Resort & Marina

Old Saybrook Center

Jenny

7.216.614 ₫

9.204.416 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A pool area with umbrellas, potted plants, and a pathway leading to a building.

A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

17. Faraway Sag Harbor

Sag Harbor

Thomas

9.078.966 ₫

11.409.947 ₫ total

includes taxes & fees

22 Nov - 23 Nov

An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.

A dining area with tables and chairs, a clock on the wall, and a counter with food items.

A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.

A living room with two sofas, a coffee table, a lamp, and a painting on the wall.

18. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Amy

2.506.415 ₫

2.882.377 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A multi-story hotel with balconies and a beach view.

A grand staircase with a chandelier, a reception desk, and a fireplace.

A large hotel with multiple balconies and a beach area with sun loungers and umbrellas.

A grand staircase with a chandelier, a seating area with chairs and a table, and a sign indicating the location.

19. Madison Beach Hotel

Madison Center

Eileen

6.832.245 ₫

7.857.082 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.

A modern bar area with a long counter, multiple seating options, and a variety of bottles and glasses on shelves.

A modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.

A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.

20. Hyatt Place Long Island East End

Riverhead

Timothy

3.415.632 ₫

3.902.359 ₫ total

includes taxes & fees

3 Nov - 4 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Where to stay in Greenport

Find the best Greenport areas for the activities you enjoy most.

Pipes Cove

A coastal landscape with a lake, dense greenery, and a sunset sky.

Pipes Cove

While visiting Pipes Cove, you might make a stop by sights like East End Seaport Maritime Museum and Railroad Museum of Long Island.

See properties

Stay near popular Greenport attractions

67 Steps Beach

9.6/10 (26 reviews)

Descend 67 wooden steps through lush greenery to reach this secluded Long Island Sound shoreline. Settle on natural boulder seats to witness spectacular sunsets over crystal-clear waters.

See properties

Kontokosta Winery

9.2/10 (48 reviews)

Long Island's only waterfront winery offers panoramic Sound views amid sustainable, wind-powered facilities. Savour award-winning wines in the modern tasting room or relax on the lawn overlooking vineyards.

See properties

Greenport Carousel

9.4/10 (50 reviews)

This 1920 Herschell-Spillman carousel features 36 hand-carved wooden horses in a harbourside glass pavilion. Try your luck at the brass ring game—catch the golden ring for a free spin on this rare historic treasure.

See properties

East End Seaport Maritime Museum

9.0/10 (9 reviews)

This maritime museum showcases Long Island's seafaring heritage with historic Fresnel lenses and lighthouse exhibits. Explore their saltwater aquarium or visit during September's vibrant Maritime Festival.

See properties

Greenport Harbor Brewing Company

This North Fork craft brewery transforms local flavours into distinctive beers in a historic firehouse. Sample specialities like Haus Pilsner while enjoying the art-filled space that captures Long Island's maritime spirit.

See properties

Railroad Museum of Long Island

9.0/10 (7 reviews)

Housed in an 1892 freight house, this museum showcases the Long Island Rail Road's pivotal role in regional development. View vintage artefacts and model train layouts while exploring transport heritage.

See properties

Safe Harbor Stirling

This upscale North Fork marina offers pristine facilities and sheltered docking for vessels up to 80 feet. Enjoy the poolside cabanas before strolling to Greenport's historic village for exceptional dining.

See properties

Greenport Farmers' Market

9.4/10 (23 reviews)

This waterfront market showcases the North Fork's agricultural bounty with local produce, seafood, and artisanal goods. Browse the stalls while enjoying live music and harbour views in scenic Mitchell Park.

See properties

Learn more about Greenport

This charming maritime village boasts a historic carousel and waterfront restaurants serving the freshest local oysters. Rent bikes to explore nearby wineries or hop the ferry to Shelter Island for beaches locals recommend when the summer crowds thin.

See all hotels in Greenport

A pebbled beach at sunset with the sun setting over the horizon.

Top Greenport Hotel Reviews

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

The Bentley Hotel Southampton

10/10 Excellent

"Perfect one day stay. I would stay here again and can recommend it to others."

Zey Hotel

10/10 Excellent

"The hotel had a good vibe and energy! Lots of artwork and was very charming. It has a bed and breakfast feel to it. The parking is behind the hotel and free and convenient. It’s right on Main Street and walking distance to all restaurants and bars. The staff especially James was warm and friendly and accommodating. We had a great time checking out all the cool lounge areas in the hotel. The room was clean and charming as well. Would definitely stay here again the next time we visit Greenport"

Water's Edge Resort & Spa

10/10 Excellent

"Great"

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"I stayed twice and borh rooms were decorated uniquely. The staff and owners were very nice. Good people"

North Fork Resort

8/10 Good

"What a great place , hidden gem on North Fork! it would have been nice if the Resturant was opened. We will be back"

Hyatt Place Long Island East End

10/10 Excellent

"."

The Harbor Front Inn

8/10 Good

"The room was clean and the staff is always wonderful. Parking was a nightmare because of the festival which had nothing to do with the hotel. My only issue is the breakfast , I wish it had a little more so I don’t have to go down the street to get something to eat . Honestly it’s not even an issue we will continue to stay here because it is a very nice hotel"

The Atlantic Hotel

10/10 Excellent

"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"

More cheap stays in Greenport

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

2.113.511 ₫

2.430.628 ₫ total

15 Nov - 16 Nov

includes taxes & fees

8/10 Very good! (1,002 reviews)

Aderi Hotel Niantic

239 Flanders Road Niantic CT

2.206.887 ₫

2.537.920 ₫ total

2 Nov - 3 Nov

includes taxes & fees

6.4/10 (745 reviews)

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT

2.506.415 ₫

2.882.377 ₫ total

15 Nov - 16 Nov

includes taxes & fees

Sleep Inn & Suites Niantic North

5 King Arthur Dr Niantic CT

2.616.346 ₫

3.008.798 ₫ total

12 Nov - 13 Nov

includes taxes & fees

The Atlantic Hotel

1655 County Road 39 Southampton NY

2.770.249 ₫

3.811.661 ₫ total

28 Oct - 29 Oct

includes taxes & fees

7.2/10 Good! (1,000 reviews)

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

3.621.240 ₫

4.137.268 ₫ total

10 Nov - 11 Nov

includes taxes & fees

9.6/10 Exceptional! (605 reviews)

Hotels in Greenport with star rating

Frequently asked questions

What's the seasonal weather like in Greenport?

The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Greenport is 1452 mm.

Explore a world of travel with Expedia

Car hire near Vietnam Veterans Memorial

Book Hotels in Greenport on Expedia.com

Find hotels in Greenport, NY from 2.430.628 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Greenport

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Greenport hotels

1. The Harbor Front Inn

2. The Menhaden

3. Zey Hotel

4. Silver Sands Motel & Beach Bungalows

5. Sound View Greenport

6. American Beech Hotel

7. Oyster Estate

8. North Fork Resort

9. Cliffside Resort Condominiums

10. The Chequit

11. The Shoals Suites and Slips

12. House on Chase Creek

13. Shelter Island House

14. Sag Harbor Inn

15. Water's Edge Resort & Spa

16. Saybrook Point Resort & Marina

17. Faraway Sag Harbor

18. Quality Inn Old Saybrook - Westbrook

19. Madison Beach Hotel

20. Hyatt Place Long Island East End

Where to stay in Greenport

Pipes Cove

Stay near popular Greenport attractions

67 Steps Beach

Kontokosta Winery

Greenport Carousel

East End Seaport Maritime Museum

Greenport Harbor Brewing Company

Railroad Museum of Long Island

Safe Harbor Stirling

Greenport Farmers' Market

Learn more about Greenport

Top Greenport Hotel Reviews

Faraway Sag Harbor

The Bentley Hotel Southampton

Zey Hotel

Water's Edge Resort & Spa

Pier Blue Inn Old Saybrook - Essex

North Fork Resort

Hyatt Place Long Island East End

The Harbor Front Inn

The Atlantic Hotel

More cheap stays in Greenport

Pier Blue Inn Old Saybrook - Essex

Aderi Hotel Niantic

Quality Inn Old Saybrook - Westbrook

Sleep Inn & Suites Niantic North

The Atlantic Hotel

The Bentley Hotel Southampton

Hotels in Greenport with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app