House vacation rentals in Cutchogue

4.95 out of 5 average rating, 230 reviews

A charming single-story house features a classic shingle exterior with a brick chimney. A spacious front deck is bordered by white railings and overlooks a manicured lawn surrounded by trees. Soft sunlight filters through the leaves, enhancing the serene setting.

Home in East Hampton

Private beach, fully updated cottage, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Superhost

The exterior of the three-story house is clad in grey shingles, accented by a vibrant turquoise front door. Multiple windows allow natural light into the interior, framing a modern yet classic architectural style.

Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

A stylish dining area is highlighted by a round table paired with modern chairs beneath a vibrant artwork. Natural light filters through large windows, providing a view of the outdoors. A cabinet with decorative items adds character to the inviting space.

5 out of 5 average rating, 9 reviews

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

The entrance of the home is framed by white, picket fencing and vibrant floral landscaping. A covered porch with classic columns supports a welcoming entrance. The door features decorative glass elements, providing an inviting touch to the exterior.

4.98 out of 5 average rating, 100 reviews

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's, and recently & lovingly fully renovated and restored. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

4.92 out of 5 average rating, 119 reviews

An open floor plan showcases a stylish living area with a comfortable seating arrangement and a large area rug featuring subtle blue tones. Natural light fills the space, highlighting the decorative elements and providing a cozy yet modern atmosphere. A smart TV is mounted on the wall.

Home in Hampton Bays

Hamptons "Get Away" Near Beach/Wineries/Golf

Located in Hampton Bays-the heart of The Hamptons surrounded by water! Close to beaches, waterfront restaurants, wineries, golf & wedding venues. Open floor plan w/ modern flair. 4 bedrooms, 2 full baths, eat-in kitchen, spacious living room and lower level recreation area/ foosball. Enjoy amenities including smart TVs/appliances, EV Charger, 2 fireplaces, 1Gb WiFi, large deck w/ string lites, BBQ, firepit, & outdoor shower. Great for families, couples, coworkers and friends!

5 out of 5 average rating, 101 reviews

A covered porch area features woven seating with bright green cushions and a chaise lounge. The wooden railing complements the light green siding of the house. Potted plants add color, while light filters through the oversized windows, providing a warm and welcoming atmosphere.

Home in Milford

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

The front exterior of the home is framed by lush greenery and a flower-lined pathway made of stone. Two trees add natural shade, while a charming yellow door welcomes guests. A fenced yard and gravel accents enhance the inviting entrance.

4.94 out of 5 average rating, 108 reviews

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 spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.

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, 16 reviews

A modern addition with large glass walls is depicted, providing views of a spacious deck and surrounding greenery. A dining area with wooden chairs sits adjacent to a hot tub, while the original cottage features windows revealing cozy interior spaces.

Home in East Hampton

Captains Quarters | July avail!

Charming traditional & at the same modern cottage with hot tub and sauna, and a fireplace inside create a peaceful and private ambiance in close proximity to the waters of Three Mile Harbor. Located on a tranquil country lane this house lets you enjoy the serene and picturesque Springs neighborhood year-round. Child friendly with fun playhouse structure and Zip line. The landscaped garden is fully fenced in and pet friendly.

4.94 out of 5 average rating, 270 reviews

A contemporary living room features a sleek gray sofa paired with a vibrant orange chair. Natural light flows through large windows, illuminating the polished wooden floor and highlighting a decorative lamp. An abstract painting adds a touch of color to the light walls.

Home in Southampton

Southampton Village Classic, Walk to Downtown!

Beautiful Southampton Village property, walk to shops, restaurants, train & jitney, no car needed! The main house includes 4 bedrooms, 3 beautiful baths, a well-stocked high-end kitchen (Viking, Bosch, Cherry Cabinets...), accommodating 8. Large deck for lounging, a seasonal heated pool and beach nearby. Quintessential Hamptons experience. Bonus cottage accommodating 3 more, bringing total to 11.

Superhost

A rocky shoreline is framed by a silhouetted tree against a colorful sunset. Clouds display shades of pink and orange as the sun sets over the water, creating a serene atmosphere. The beach area offers a peaceful view of nature.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

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$.

An open-concept living space is highlighted by a wooden dining table set with neutral décor. A comfortable seating area features a dark couch and large windows allowing natural light. Ceiling fans provide airflow in this bright and airy environment.