House vacation rentals in Sag Harbor

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 house, 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.

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, 101 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.

4.89 out of 5 average rating, 100 reviews

A spacious living room features cathedral ceilings and a fireplace, surrounded by large windows that allow natural light to fill the space. Comfortable seating is arranged around a circular coffee table, complemented by decorative nautical elements on a cabinet.

Home in Hampton Bays

Hamptons Escape minutes from Beaches and Nightlife

This spacious traditional home features an inviting entryway that flows into a light-filled living room, leading to a lovely outdoor area. The ground floor includes a large master suite, a living room with cathedral ceilings and a fireplace, a dining room, and a fully equipped kitchen. Upstairs are two additional bedrooms and a bath, all with a bright feel. The property offers various outdoor spaces and is a short walk to the bay and ocean beaches. Pool available Memorial Day to Labor Day!

A spacious gourmet kitchen is equipped with white cabinetry and a large island featuring a light-colored countertop. Pendant lights hang above the island, and stainless steel appliances are visible in the background, complemented by a tile backsplash and modern fixtures throughout.

4.94 out of 5 average rating, 34 reviews

Luxury by the Sea!!

Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. This home is beautifully designed with too many architectural details to list. Property is fully furnished 🛋 with no detail spared . Open floor plan, spacious great room with gas fire place and flat screen, gourmet eat 🍝 in kitchen with large island is a wonderful place to entertain 🥂. Brand new washer/dryer, butlers pantry and mud room. Where the country meets the sea 🌊

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!

Superhost

A spacious living room is defined by a sectional sofa, complemented by a wooden coffee table at the center. Natural light filters through large windows adorned with sheer curtains. Light-colored walls and decorative wall art enhance the inviting ambiance.

Home in East Hampton

4.83 out of 5 average rating, 6 reviews

Cozy Town Cottage - Minutes from EH Town

This charming, historic home is perfect for a young family! The original mudroom with laundry, farm kitchen (no dishwasher), spacious dining and living rooms, two bedrooms and one bathroom welcome you on the main level. Upstairs is a larger bedroom and a second bathroom as part of an open primary suite. Take a half mile, tree-covered walk to town, or stop at the grocery store or restaurants just down the street. Sorry but, absolutely no animals as owner has severe allergy.

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, 109 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.

4.89 out of 5 average rating, 105 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.

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

Hay 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.