Greenport vacation rentals

4.86 out of 5 average rating, 28 reviews

A waterfront gazebo is depicted, featuring a round table adorned with a vase of flowers. Two white chairs are positioned around the table, and autumn foliage adds warmth to the scene, with the glistening water visible in the background.

Villa in New London

Waterfront Holiday Vacation Villa New England

Have fun with the whole family at this stylish VILLA with water (kayak) access to Ocean State Beach Park and a 4 minute drive to the quaint Waterford Beach. This idyllic leisure home has everything you need to enjoy your gateway. SECLUDED setting with 300 ft of waterfront access for kayaking , fishing. Sauna, bicycles, waterfront gazebo with fire pit , basketball hoop and hammocks. All spaces are newly renovated and tastefully decorated. New fully stocked kitchen . Close to Mystic - Foxwoods

4.79 out of 5 average rating, 43 reviews

Two comfortable chairs are positioned on a spacious porch, offering a clear view of the beach and ocean. The horizon is visible in the distance, with calm waters under a blue sky dotted with clouds.

Home in West Haven

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

4.9 out of 5 average rating, 99 reviews

A charming building is illuminated by soft evening light, surrounded by blossoming trees adorned with twinkling lights. Outdoor seating is visible, inviting guests to enjoy the vibrant atmosphere of the town. The sky transitions to a serene twilight blue, enhancing the scene.

Guest suite in Branford

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

4.94 out of 5 average rating, 108 reviews

An open kitchen space features modern appliances, including a stainless steel stove and ample counter space. Barstools are positioned at a breakfast bar, while natural light illuminates the area through several windows. Warm wood flooring complements the neutral-colored walls.

Home in North Fork

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

4.88 out of 5 average rating, 102 reviews

A covered outdoor seating area is furnished with a combination of turquoise and brown seating, complemented by decorative pillows. Soft lighting from string lights enhances the space. A swing seat is positioned against the wall, and a small table is centered on the tiled patio.

Home in Mastic

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

5 out of 5 average rating, 11 reviews

A view of the Peconic River is depicted from a wooden deck, featuring a small round table and two woven chairs. The water reflects clear blue skies, with boats visible in the distance and trees lining the shore.

Houseboat in North Fork

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

4.82 out of 5 average rating, 67 reviews

A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. Beach grass and wooden fencing line the path leading to the water, where a lifeguard stand is positioned for safety.

Home in Hampton Bays

Spacious Hamptons Oasis | Perfect for Families

Escape to our stunning year-round retreat in Hampton Bays' Red Creek area. With over an acre of lush land, our charming residence offers unparalleled serenity and tranquility just minutes from local bay, beaches, and wineries. Ideal for family fun, friend retreats, and exquisite dining in the Hamptons. For off-season activities, explore wineries, animal feeding farms, apple and pumpkin picking, breweries, and more. Book now for your dream getaway!

4.9 out of 5 average rating, 115 reviews

An outdoor deck area is seen featuring a large round table surrounded by several comfortable chairs. A sun umbrella provides shade, while a propane grill is positioned nearby. Lush trees create a natural backdrop, enhancing the serene atmosphere of the space.

Home in Shelter Island

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

4.98 out of 5 average rating, 179 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in North Fork

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Cottage in Shelter Island

A traditional New England house is set in the central village of the island, surrounded by lush green lawn. Tall trees provide shade, and the late afternoon sun creates elongated shadows across the grass, highlighting the inviting outdoor space.

4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Greenport vacation rentals

Laptop-friendly workspace

Stay near Greenport's top sights

Noah's103 locals recommend

Kontokosta Winery75 locals recommend

The Frisky Oyster75 locals recommend

Aldo's Coffee Company53 locals recommend

Little Creek Oyster Farm & Market53 locals recommend

American Beech52 locals recommend

Apartment rentals in Greenport

4.82 out of 5 average rating, 119 reviews

The exterior of a three-story house features light grey siding with turquoise shutters. A welcoming front porch contains multiple windows, and the entrance is accentuated by a small flight of stairs. Lush greenery surrounds the property, enhancing its appeal.

Apartment in North Fork

House on First

4.86 out of 5 average rating, 178 reviews

A well-furnished living area features a dark gray sofa paired with colorful cushions and an accent chair. A small side table sits beside the chair, and a lamp illuminates the space. Art adorns the walls, and a soft area rug adds warmth underfoot.

Apartment in East Rock

2 Bedroom apt quiet courtyard setting w parking

4.96 out of 5 average rating, 142 reviews

The open living area features a high vaulted ceiling with exposed wooden beams, creating a spacious environment. Light-colored sofas are arranged around a wooden coffee table on a dark rug, with an adjacent dining area visible in the background.

Apartment in North Fork

Upscale Newly Constructed Apartment

Apartment in Shelter Island Heights

A spacious living area features a mixture of seating options, including a modern white chair and a cozy sofa. A large area rug anchors the space, accompanied by decorative pillows and books on a low table. Natural light fills the room through large windows beneath exposed wooden beams.

4.91 out of 5 average rating, 245 reviews

Squire Chase House

4.87 out of 5 average rating, 126 reviews

A private entrance features a white door set against a backdrop of textured wooden siding. Colorful purple irises bloom along the stone pathway, complemented by lush greenery, contributing to the inviting exterior of the studio apartment.

Apartment in Southampton

Southampton Village Studio

4.9 out of 5 average rating, 112 reviews

A comfortable living space features a dark sofa and an inviting wooden coffee table. Behind it, a work desk with a chair is situated next to a bookcase filled with decorative items. A soft light illuminates the room, complemented by the warm tile floor.

Apartment in East Rock

Sperry House one bedroom private apartment

Apartment in Hampton Bays

A cozy interior space features white walls and a wooden ceiling with recessed lighting. A guitar leans against a wall, near a stone fireplace. A sofa and a modern wooden coffee table are arranged for relaxation. A spacious bed is positioned in the corner by a window.

4.97 out of 5 average rating, 104 reviews

Walk to Bay and Ocean-Newly Renovated

4.86 out of 5 average rating, 111 reviews

A cozy seating area is featured, with plush, textured cushions arranged on a built-in bench. A wooden table stands beside two rustic chairs, both enhancing the relaxed atmosphere of the space. Natural light filters through sheer curtains, illuminating the warm wooden flooring.

Apartment in Montauk

Recharge at our Renovated ocean front unit

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Other great vacation rentals in Greenport

4.87 out of 5 average rating, 153 reviews

Large windows allow natural light to fill the open living space, showcasing the stunning view of the Great South Bay. A comfortable sofa with decorative pillows faces the water, complemented by a dining area nearby. Warm wood tones enhance the cozy atmosphere of the room.

Cabin in Shirley

A-Frame cabin with private beach & epic sunsets

4.99 out of 5 average rating, 136 reviews

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

5 out of 5 average rating, 9 reviews

A waterfront balcony is featured, showcasing wood paneling and a clear view of the water. The deck is equipped with a railing and lights, offering a relaxing spot to enjoy the scenery. The sunlight casts shadows along the planks, highlighting the serene environment.

Home in North Fork

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

4.89 out of 5 average rating, 99 reviews

A bright living room features a high wooden ceiling and large windows, allowing natural light to fill the space. Comfortable seating options include a spacious sofa and woven chairs. A decorative area rug is positioned on wood flooring, creating a cozy gathering place.

Home in Hampton Bays

Hamptons Escape minutes from Beaches and Nightlife

4.94 out of 5 average rating, 18 reviews

A serene beach scene captures gentle waves lapping at smooth stones along the shoreline. Soft, sandy areas are visible in the distance, with greenery lining the coast. A cloudy sky provides a soft light over the tranquil waters.

Home in Waterford

Summer Beach Cottage Harknes, Ocean Beach N

4.89 out of 5 average rating, 484 reviews

A shoreline is depicted with a mixture of smooth, round pebbles covering the sand. Gentle waves are seen rolling onto the beach, and a colorful sunset fills the sky, casting reflections over the water's surface.

Cabin in Rocky Point

Great little place just for a couple

Guesthouse in Shelter Island

A spacious outdoor area is highlighted by a refreshing pool surrounded by lounge chairs. The pool house, featuring a white exterior, sits in the background amidst lush greenery. Flower pots and garden plants frame the scene, enhancing the tranquil environment.

4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House