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Cottage vacation rentals in Greenport

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Greenport cottage rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

A spacious dining area features a long wooden table surrounded by several chairs. A large pendant light hangs above, casting soft illumination. Colorful wall accents and artwork complement the warm wooden flooring, while an adjacent kitchen can be seen in the background.
Cottage in The Hamptons

3 bedroom Hamptons cottage 5 mins from beach

Top guest favorite
The exterior of a charming cottage showcases natural wooden shingles, surrounded by lush greenery and vibrant shrubs. A wooden staircase leads to a covered porch, where large windows allow glimpses of the interior. The serene outdoor environment evokes a peaceful setting.
Cottage in The Hamptons
5 out of 5 average rating, 10 reviews

Walk/Bike to East Hampton Village & Ocean Beaches

A charming red cottage is framed by lush greenery, set back from a driveway leading to the entrance. A small white bench is visible on the left side of the well-maintained lawn, with flowering plants adding a touch of color in front of the house.
Cottage in North Fork
4.68 out of 5 average rating, 205 reviews

Lovely 2 BR Beach House No. Shore

Guest favorite
A serene backyard is showcased, featuring a stone patio, a vibrant flower garden in colorful pots, and a tranquil pond with a water feature. A hammock is suspended between two trees, offering a relaxing spot surrounded by greenery.
Private room in The Hamptons
4.82 out of 5 average rating, 107 reviews

Private Room in the House that Art Built

Guest favorite
An open-concept living space features a modern dining area with a wooden table set for six, complemented by sleek metallic chairs. A comfortable sectional sofa is positioned across from a wall-mounted television, with a fireplace and green outdoor views visible through large windows.
Cottage in The Hamptons
4.95 out of 5 average rating, 95 reviews

Calf Creek Cottage (Water Mill/Bridgehampton)

Pet-friendly cottage rentals

Guest favorite
An open living space is presented, featuring a modern kitchen with stainless steel appliances and a white circular dining table surrounded by black chairs. A large television is mounted on a white cabinet, and light enters through a nearby window.
Cottage in The Hamptons
4.93 out of 5 average rating, 98 reviews

Hamptons Cottage.

Superhost
A cottage is nestled among a lush garden with blooming flowers and manicured grass. The exterior features a combination of green siding and gray shingles. Pathways made of stones lead to the entrance, embracing a serene and inviting environment.
Cottage in The Hamptons
4.8 out of 5 average rating, 20 reviews

Southampton cozy cottage by the beach.

Top guest favorite
A well-maintained garden is visible, featuring a variety of blooming flowers, lush green grass, and manicured hedges. A white picket fence marks the entrance, with an inviting pathway leading into the garden. A large tree and complementing foliage create a serene outdoor environment.
Cottage in North Fork
4.98 out of 5 average rating, 45 reviews

New Suffolk Beach Cottage 1 | North Fork

Guest favorite
A spacious living area is highlighted by a stone fireplace, flanked by large windows that provide ample natural light. Wooden beams run across the ceiling, complementing the neutral-toned furnishings, including a cozy sofa. A dining table is visible in the background, surrounded by greenery.
Cottage in The Hamptons
4.98 out of 5 average rating, 47 reviews

Chic cottage on lush, secluded acre by the beach.

Superhost
A light-colored boat is anchored in calm water, surrounded by lush greenery. Reflections of the boat can be seen on the still surface, while distant homes are visible along the shoreline under a clear blue sky.
Cottage in The Hamptons
4.87 out of 5 average rating, 91 reviews

Waterfront Beach Home & Garden —AC, BBQ, Kayaks!

Guest favorite
A compact living area features a blue sofa adorned with patterned pillows and a geometric area rug. A dining table with two wooden chairs is positioned near a mirror reflecting natural light from the window. Potted plants add a touch of greenery to the space.
Cottage in The Hamptons
4.85 out of 5 average rating, 91 reviews

Cottage 3 minute walk Bridgehampton town

Top guest favorite
A spacious lawn is bordered by tall trees, providing a natural frame for the cottage. The vibrant green grass leads to a serene waterfront, where the lake reflects the sunlight. The peaceful setting invites relaxation and outdoor activities.
Cottage in The Hamptons
4.97 out of 5 average rating, 73 reviews

Head of Pond House - Waterfront Cottage

Top guest favorite
A serene beach scene features soft, sandy shores bordered by gentle green grasses. The calm water reflects the clear blue sky, with a few clouds visible in the distance. The setting conveys a tranquil environment, perfect for relaxation and exploration.
Cottage in The Hamptons
5 out of 5 average rating, 44 reviews

walk to bay, woods cottage

Private cottage rentals

Top guest favorite
A spacious outdoor area is featured, highlighted by a heated pool surrounded by lounge chairs. Green grass extends throughout the yard, with trees providing shade in the background. A pergola is visible, creating an inviting space for outdoor gatherings.
Cottage in The Hamptons
5 out of 5 average rating, 14 reviews

The hidden gem of the Hamptons

Guest favorite
A charming country cottage is framed by lush green trees, showcasing a well-maintained exterior with dark wood siding. The driveway leads to a garage, and flower beds enhance the entrance. The surrounding yard offers ample greenery, contributing to a peaceful atmosphere.
Cottage in The Hamptons
4.94 out of 5 average rating, 53 reviews

Southampton Village Cottage

Top guest favorite
A cozy living area features a light-toned sofa complemented by a stylish armchair. Skylights illuminate the space, highlighting the wood flooring and modern decor. A flat-screen TV is mounted on the wall, and a bookshelf adds a touch of character with various books.
Cottage in The Hamptons
4.91 out of 5 average rating, 150 reviews

East Hampton Fisherman’s Cottage with Secret Bath

A single-story house is set against a backdrop of green grass and towering trees. Natural light illuminates the exterior, which features light-colored siding and a welcoming front porch. The spacious yard provides ample outdoor space for relaxation.
Cottage in North Fork
4.97 out of 5 average rating, 109 reviews

Riverhead Farmhouse

Superhost
A sandy beach stretches along the shoreline, meeting calm blue waters under a clear sky. A wooden staircase leads down to the beach, surrounded by sparse vegetation and rocky areas. Soft clouds drift above, contributing to a serene coastal scene.
Cottage in North Fork
4.91 out of 5 average rating, 34 reviews

Pumpkins & Sunflowers! Cozy Cottage in the Fall!

Top guest favorite
A light-filled living area features a white sofa with green accent pillows, complemented by a glass coffee table topped with stacked books. A guitar rests beside a side table, and large windows with woven shades provide a view of the outdoors. The space includes a dining area in the background.
Cottage in The Hamptons
4.98 out of 5 average rating, 106 reviews

Sag Harbor Cottage

A serene view of the Long Island Sound at sunset, with soft waves reflecting golden light. The sandy beach is lined with smooth stones and boulders, framed by a gentle shoreline. The sun descends towards the water, creating a calming atmosphere.
Cottage in South End
4.73 out of 5 average rating, 56 reviews

Newly Renovated 2-Bedroom Home on the LI Sound

Guest favorite
A charming cottage is framed by vibrant pink azaleas, enhancing the exterior's appeal. Lush green grass surrounds the home, and a clear blue sky provides a bright backdrop. Windows allow natural light to fill the interior, which features a welcoming porch area.
Cottage in Shelter Island
4.96 out of 5 average rating, 48 reviews

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

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