27,207 properties available

Located in Greenport, New York, United States. Waterfront house on steerling harbor, views from every room. Fully furnished monthly, summer or year round rental on Sterling Harbor with spectacular views out to Bay. A five minute walk to downtown Greenport. This stunning 3 bedroom, 4 bath home boasts hardwood floors, lots of windows and a gourmet chef's kitchen with granite counters. Floating dock/boat slip directly in front may be available under separate agreement. Surrounded by vineyards and farm stands, come enjoy the North Fork.

Located in Greenport, New York, United States. Newly renovated farmhouse - steps to Greenport Village Luxury home on a quiet street in the Village of Greenport. This brand new Farmhouse has been fully renovated with all modern amenities - a quick walk to town and local vineyards!This gorgeous home is bright with sunshine and hard wood floors throughout. Effortless beachside living. Oversized private backyard is fully fenced in. Sleep comfortably in the brand new tempur-pedic beds throughout.

Located in Greenport, New York, United States. American Beech in Greenport - Deluxe King Suite 12 The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments. Our guests pay a resort fee of $35 per night, including additional taxes at check in. Our room 12 comes with a fully stocked mini-bar and mini-fridge, Smart TV, glass shower door and bathtub, iron, ironing board, hairdryer and Maison Margiela amenities. Each room has robes, Frette beach towels, and heated floors to make your stay as comfortable as possible. We also provide a Nespresso machine in room. If there is anything else you need, please let us know! Please note: In order to access this room, you are required to climb one f

Located in Greenport, New York, United States. Greenport Village - Spacious 3-Bedroom, 3-Bath Bungalow Newly renovated 1800 square feet bungalow home in the heart of Greenport Village (~12-minute walk to restaurants in town). 3 bedrooms, 3 full baths, one den/bonus room (has a private bath and can VERY comfortably fit an air mattress) and top of the line amenities. Great destination for families (no pets); house comfortably sleeps 6 adults and has a large fenced-in backyard with Adirondack chairs and a dining set for six people. Amazing natural light throughout the home.The spaceOur bungalow offers 3 full bedrooms (one king, one queen, one full) plus a converted en suite den downstairs that can comfortably fit an air mattress. The house offers 3 full bathrooms, a top of the line kitchen, and a spacious backyard. Guests have access to the whole home with the exception of the attic and one closet.Key residence features:-Fully equipped kitchen (plates, cups, utensils, etc.)-Central air conditioning-Washer and dryer-Indoor dining tabl

Located in East Marion, New York, United States. Dog-Friendly Beachfront Home w/Deck, Free WiFi, Ocean Views, & Wood Fireplace North Fork Waterfront GemOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'A breezy beach-cation awaits at this marvelous and well-located, dog-friendly home! North Fork Waterfront Gem truly lives up to its name–it's located on the beachfront, offering jaw-dropping views of the ocean and it's a gem of a home. Spend memorable times relaxing in the living room, which boasts an inviting sofa, an armchair, a rocking chair, and a flatscreen TV with streaming services. There's an ocean-facing desk, the perfect spot to sit down, reply to some work emails, and still relax. A wood-burning fireplace will keep you all nice and warm during your stay. However, if you visit during the summer months, don't hesitate to unwind in the oceanfront deck. Take a book with you, put your sunglasses on, and take advantage of the two chaise lounges w

Located in East Marion, New York, United States. North Fork seaside retreat for design lovers A thoughtfully renovated, direct waterfront home on Long Island's North Fork. Situated on the coveted bay side, where the waves are calmer and the water is warmer. Designed with rare vintage and design furniture — Corbusier, Hans Wegner, Noguchi, Ingo Maurer. Radiant floor heat throughout the house. Water views on three sides in the living room and kitchen.Two bedroom, two bathroom. Perfect for solo travelers, couples, and small families looking for a quiet place to work, write, or get away.Wake up and fall asleep to the sound of waves. Enjoy bright pink sunrises on the deck with a good cup of coffee or tea.Located within minutes of the area's best local farm stands, fantastic restaurants in Greenport and Orient Village, and the Hampton Jitney, LIRR, and Shelter Island Ferry.IG: @eastendseahouse

Located in Greenport, New York, United States. American Beech in Greenport - King Suite 3 The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments. All of our rooms come with a fully stocked mini-bar and mini-fridge, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. Each room has robes, Frette beach towels, to make your stay as comfortable as possible. We also provide a Nespresso machine with complimentary coffee to enjoy. Our bicycles and WiFi are also included in this great complimentary package! If there is anything else you need, please let us know! Please note: In order to access this room, you are required to climb one flight of stairs —

Located in Shelter Island, New York, United States. Shelter Island Retreat With Pool ...A Stone's Throw Away From The Beach! * Please Read House Rules And Policy's Before Booking*Perfect For Families!! New to the rental market in 2022! Located within close proximity to Sandy beach with sunsets galore and resort areas, this neat-as-a-pin home has all the ingredients for an exciting summer vacation. Tucked behind evergreens, the rooms are sun-filled in an open plan. Just inside the foyer the living room has a extra large Queen sized sleeper sofa beautiful windows out to the veranda, fireplace and entry to a well equipped kitchen, which then flows into the dining area which has French doors to the entertainment deck. Down the hall is a full bath, a guest bedroom with bunk bed w/ trundle, a second guest bedroom with a queen sized bed, home office area and door to the pool deck, plus the primary en-suite bedroom. The lower level has a projection screen media room, comfy recliner chairs and laundry area. The grounds are what summer is all abo

Located in Shelter Island, New York, United States. NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE! Sleeps 4 adults (max) or total of 6 with kids.Perfect family getaway.Shelter Island Rental License #: 2023-V-0018Weekly and Monthly Discounts for Winter Rentals!Stay at our newly renovated, light filled home! In the warmer months lounge by the heated pool in the private tree-filled yard, relax in the hot tub that overflows into the pool, nap in the shade of the pool house, then rinse off in the outdoor shower. Read a book in the hammock or on the porch rocking chairs. BBQ on the big back deck and hang out by the outdoor fire pit to roast marshmallows in the evening. **Pool & hot tub CLOSED NOVEMBER - MAY. In the colder months, stay in the mid-century modern style living room, play board games and watch a movie on Netflix with a roaring fire in the stone fireplace or walk to the best sledding on the island. Cook in our well appointed kitchen and eat while watching the sunshine and stars through the dining room skylight. You wi

Located in Shelter Island Heights, New York, United States. The Ultimate Beach House This is a 2 house property that can sleep up to 15 if necessary. The Main house has 4 bedrooms and 3 baths, while the cottage has 3 bedrooms and one bath -- as well as an outdoor shower! You can rent one or both--it is up to you! The homes sit on a little over an acre of property and are walking distance to beautiful Hay Beach! Sit by the pool in the backyard, if you just want to stay at home and relax. Enjoy a barbecue and outdoor seating at both homes for additional living space. Each home also has laundry. There are bikes for use to explore the island. Many restaurants to choose from too. At this rental you can have the room to relax and spend time with others.

Located in Southold, New York, United States. Waterfront, private beach, ready for adventure, light & bright! Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water views from every room, this light and airy 4 bedroom, 2.5 bath property is the perfect North Fork retreat! Coastal furnishings, with a large deck and grounds, enjoy paddle boarding, kayaking, and swimming right from your own beach. Or take a bike ride or short drive to hamlet shopping, restaurants, transportation, award winning wineries, and Peconic Bay and Long Island Sound beaches. The ultimate North Fork vacation awaits!4 Bedrooms, 2.5 baths, 3200 square feet• Great room with cathedral ceiling and direct views of Long Creek• Family room/den with 65” smart TV with Netflix/Amazon/Disney access and 300 Mbps wireless Internet (includes Eero mesh network for full house/deck WiFi coverage and 3 desk work spaces)• Newly renovated well-equipped kitchen with eat-in counter space including new gas Wolf 6-burner range and built-in Bosch

Located in Southold, New York, United States. North Beach Fork Beach House Enjoy our tranquil home in a private beach community.Located on a half acre of private land, this home has all the amenities you will need for a relaxing vacation or getaway. Views of Peconic Bay from the home, a private beach .Take advantage of Historic Greenport, located just 1 mile away, as well as the Ferry to Shelter Island and Sag Harbor, along with three restaurants just walking distance away.Home has an open concept feel with catherdal ceilings, great room, kitchen and dining room with sliding glass doors that leads to a large deck. The deck wraps around to the front porch.NOT A SHARE HOUSE OR USE FOR AFTER PROM.

Located in Southold, New York, United States. Renovated American Farmhouse in the heart of Southold with heated saltwater pool Our newly renovated Farmhouse is centrally located in Southold with easy access by bus, train or car. Enjoy your morning coffee as the sun rises over the farmfield. Spend an afternoon exploring the beauty of the North Fork, soak in the sun at one of the beautiful Peconic Bay or Long Island Sound beaches, enjoy live music at numerous wineries and/or breweries, browse unique local finds at one of many antique and/or quaint shops, and don't forget to stop by the bountiful farm stands. Cool off with a dip in the heated saltwater pool, enjoy dinner under the stars and reminisce around the fire pit.

Located in Shelter Island, New York, United States. Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve 3 bedroom, 2 bath house in Shelter Island offers many amenities including pool, dock, private beach access and great coastal hiking in the 2,000 acre Mashomack Preserve. Close to the south ferry with easy access to Sag Harbor and the Hamptons. It is the perfect house to get away from the hustle of the city to relax, soak in the sun and enjoy the gourmet chef’s kitchen and herb garden and 2 grills.The open plan house has a granite eating counter, dining room and a large deck overlooking the pool with an outdoor dining and lounging. The large property comes with a paddle board and 4 bikes to explore the beautiful island.There are 3 bedrooms, including a master en suite.

Located in Cutchogue, New York, United States. North Fork Beach House - short walk to Peconic Bay and beach This wonderful beach House is located in the beautiful Fleet's Neck neighborhood facing the Peconic Bay. It is less than a 5 minute walk to the beach along with easy beach parking. The nearby beach has beautiful views filled with sailboats in the summer. The house is a mile to King Kullen supermarket, Braun Seafood, a variety of vineyards, Greenpoint Brewery and many farm stands. The house has 3 bedrooms and sleeps 6 comfortably. It is situated on 1/2 an acre lot, with water views, a lawn to play and an outdoor shower. There is a spacious outdoor deck for grilling, cocktails or a morning coffee. It is 90 miles from NYC, 15 minutes to Greenport and 25 minutes to Orient Point Ferry.

Located in Southold, New York, United States. Steve's Place: Heated Pool, 3BR Southold Home, Beach Steve's Place is a beautifully and professionally decorated 3-bedroom with 1.5 bathrooms, North fork vacation home is just a ten-minute drive into town and about a ten-minute drive to the beach. Everything you would possibly need and want for a wonderful stay is here!This home sleeps six perfectly with three queen-sized beds and has a beautiful, remodeled kitchen, perfect for the chef in the family. Plenty of seating in the living room area to enjoy some family time together or just relax with a great movie or a fabulous book. We are pet-friendly so bring the whole family. The home is located in a quiet beautiful neighborhood and the yard is a wonderful fenced-in retreat with a Beautiful heated pool, cozy lounges, gas barbecue, and outdoor seating up on the deck with views of the pool and garden, just wonderful.This is a wonderful vacation home!You will absolutely love the town of Southold with all the small shops and great restauran

Located in Southold, New York, United States. North fork Private exclusive Residence for Rent Spacious 3 bedroom ...3 1/2 bathroom modern house with large swimming pool .close to the beach and vine yards. Large eat in kitchen. Wolf appliances.....granite island. dining room ....tv room with bar for entertainment...Reading / Sunroom, With access to a large back grassed yard leading out to a large salt water swimming pool....with bbq....living room and indoor gas fire .... Master bedroom. King bed. Large couch ...large walk in closet and a full bathroom. Second bedroom king bed ...large closet n third bedroom queen bed. All bedrooms have TVs...

Located in East Marion, New York, United States. Bohemian Old Life Saving Station with Beach & Pool ONLY 1 WEEK RENTALS FROM MID JUNE TO MID SEPTEMBERRENTALS ARE FROM FRIDAY TO FRIDAYAVAILABILITY FOR JULY & AUGUST IS ONLY DECIDED IN LATE SPRING- WILL NOT BE ABLE TO BOOK ANY JULY- AUGUST DATES UNTIL AT LEAST END OF APRIL.Please do not inquire about staying less than a week during these months.This super romantic six-bedroom house was originally built as a coast guard life saving station in 1893. It has been beautifully renovated, and furnished with vintage furniture, to maintain its classic farmhouse charm, but with many modern conveniences.This is a family house, used by it's owners throughout the year and lovingly lived in.As seen on HBO's "Girls" & "The Undoing"There is a huge kitchen and dining room with two sinks, two ovens, a six-burner WOLF stove and a huge amount of work space. With abundant farm stands and fresh fish at your fingertips, this kitchen is the ideal place to cook and entertain. The large table seats 14, allowi

Located in Cutchogue, New York, United States. Spacious New 4 Bedroom Home With Pool on 2 Acre Property New 4 bedroom 3 1/2 bathrooms with built in pool on a 2 acre private setting. A perfect place to unwind away from it all. Close to a beautiful bay beach. Plenty of vineyards close by for wine tastings. Home has four bedrooms, two have private bathrooms and two share a bathroom. The pool area has 8 lounge chairs with cushions, making it a perfect place to relax. The deck off the kitchen has a table and umbrella, perfect for outside dining. The house is perfect for 4 couples or two families with children. Owner has apartment that will be used during your stay.

Located in Greenport, New York, United States. New Four Bedroom Greenport House Sleeps 10 Spacious Greenport 2600 square foot Four Bedroom Cottage Beach Bungalow. Five minute waking distance to Greenport Village (restaurants, bars, coffee shops, shopping and much more) Near 5th & 6th Street Beach & Park , Shelter Island Ferry, Train and Carousel. Located in the area of amazing food, entertainment, relaxation, vineyards, breweries, parks, beaches and much more. You can walk to all!Four bedrooms (3 with queen beds, one with 2 queen beds, sofa sleeps 2 and fully stocked Eat in Kitchen (dishwasher, microwave, Keurig machine) Dining Room, Laundry Room, Living Room with TV. Plus Indoor Porch/Sitting room with sleeper. Cozy yard with outdoor furniture and Weber barbecue. Large Umbrella for shade. Plenty of closet space. Amazing linens. Cable and Fast Speed Wifi.2024 Rates : July 1st -End of August Four Night Minimum StaySeptember 3 night stayOther Months Two Night Minimum Stay*Holiday Weekends are Four Night Minimum Stay (Memorial Da

Located in Southold, New York, United States. 4BR+ Newly renovated home mins to top beaches and vineyards, new heated pool! This is a newly renovated 4BR+ home in the heart of Southold with a brand new 18 x 36 heated pool and fully fenced yard. Just minutes from beautiful beaches and vineyards. The house situated on a 1/3rd of an acre and is within a short walk of a private beach and an incredible award winning vineyard. It has 4 bedrooms plus a separate den/office/bonus room. The property has many amenities including use of a kayak, bicycles, full kids swing set / jungle gym, fire pit, patio and barbecue.It is just a short drive to dozens of other beaches, vineyards, farms, Southold/Greenport villages, Shelter Island, restaurants, historical sites and many more charming places on the North Fork.A beautiful spot for an escape from it all - perfect for families!

Located in Sag Harbor, New York, United States. PVT Sag Harbor Beachfront community - Saline Solar Hted Pool, Community Tennis. Escape to your private oasis where tranquility meets convenience in a private Sag Harbor/North Haven beachfront community with a beautiful bay beach right down the block and community tennis. This perfect location with privacy all around offers wide span of east-facing beach for swimming, kayaking, paddleboarding, and fishing—plus gorgeous sunrises. Easy access to myriad of activities minutes away in Sag Harbor Village.The well-appointed, light-filled traditional home with two gas fireplaces has three spacious en suite bedrooms (including first and second level primary rooms); plus a bonus den with convertible queen sofa bed, sleeps six plus additional - occasional overnight guest in den- new queen sofa bed. Open floor plan with bright open kitchen and Dining room. Large bright living room with fireplace and piano. Open views to the pool, and an additional exterior entrance. The first level features

Located in Shelter Island, New York, United States. Serene vibes with natural sunlight and tranquil salt water pool. This 1960's A-Frame is flooded with natural light - open zen vibe and a tranquil backyard with a salt water pool and cabana. This house features large IPE deck in front and back - outdoor fire pit, ping pong table, 2 outdoor showers and clean simple lines. The house has two bedrooms , two full bathrooms and a sleeping loft.Central Air , Fireplace , washer / dryer , Henry Built Kitchen and full basement. Sheets and towels provided. Pool maintenance provided.Cleaning crew between each rental provided.

Located in Southold, New York, United States. Sprawling waterfront home with bikes, kayaks, pool table, and grill - dogs ok The North Fork Beach HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Right across the street from Little Peconic Bay, this five-bedroom home provides the perfect place for your family on your next vacation! With direct water views and access, fun in the sun is inevitable. When you aren't swimming, boating, or fishing, head to one of the nearby wineries for an afternoon tasting, apple pick at one of the local orchards, or ride horseback with the serene Southold landscape as your backdrop. After a day full of adventure, head back to your retreat where you will instantly take notice of the spacious front porch, the ideal spot for your morning ritual cup of coffee or late-night chats. The sunny living room provides a peaceful place to sit, visit with your loved ones, and tune into your favorite TV shows and movies. The fu