94,639 properties available

Located in Shelter Island, New York, United States. Hilltop Cottage Privacy Abounds Private Hilltop Cottage on 1.5 acre lot bordering horse farm. Feel the stress melt away. Centrally located within walking distance to restaurants, golf, and beach. Clean, cozy, 3 bedroom with 2 full baths, wood stove, grill, washer & dryer, full kitchen, and dining room. Bikes and games, too.

Located in Cutchogue, New York, United States. Perfect Cutchogue/Southold -North Fork Vacation Home. Very Private, close to all Enjoy this entire newly furnished house. Beautiful North Fork Country Home with beds for 6. Private fully fenced back yard . Dogs are welcome w/ owner approval. Sorry no cats. Backyard features patio with grill, table and covered patio seating. Outdoor shower on side of house. Two cornhole boards with bags and a firepit with chairs.This home is powered by a groundwater heat pump which provides environmentally efficient central heating and cooling. On a sunny day the solar array on the roof provides a completely carbon neutral stay.Bring your kayaks. Steps to the creek with quick access to the Peconic bay. Explore the beautiful North Fork wetlands. Bring your bike and bike to the wineries or the Greenport brewery. 2 miles to beach, wineries, breweries, restaurants, pumpkin picking, farm stands and all the North Fork has to offer. Short ferry ride from Greenport to beautiful Shelter Island. Contin

Located in Cutchogue, New York, United States. Charming Country Home, Minutes to Sandy beaches, in the Heart of Wine Country This charming country home is centrally located right in the heart of wine country and minutes to sandy white beaches. Short walk to Peconic Bay Winery, King Kullen Shopping Center, Braun's Seafood, Michaelangelo's Restaurant and Cutchogue Village. Short drive to the outlets and Aquarium located in Riverhead. Stroll through the historic village of Greenport, enjoying the waterfront, stop at Claudio's to enjoy your favorite beverage and bands on the weekend. Don't forget to stop at your favorite winery on the weekends, bring your picnic baskets and enjoy the music. Bask in the beautiful view of the sound from the deck of Sound View Restaurant while savoring your delicious dinner. The Hamptons and the ocean is just a 30 minute drive away. Spend a delightful day going to the Montauk Lighthouse and grabbing lunch at the docks in Montauk. Internet Access & WiFi Provided. Will consider monthly rates fro

Located in Southampton, Massachusetts, United States. Hamptons Bay Front Beach House with Private Boat Dock Available Memorial Day-Labor Day. This 3 Bedrooms, 2 Bathrooms + Outdoor Shower is on the PeconicBay in South Hampton/Noyak Road, 10 min from Sag Harbor and South Hampton. The house comes with a private dock that is located on the pond across the road. Bring your boat and enjoy it from the comfort of your home. Enjoy your own private beach on the bay, this 1960 "ranch style" beach house is very peaceful and extremely well located so you can enjoy everything that the Hamptons has to offer. Pricing: MD-LD = 70,000. June: 20,000 July: 25,000 August: 25,000.

Located in Southold, New York, United States. Southold home at Kenney's Beach 4 bedrooms Lovely, spacious home with open, airy floor plan, featuring four bedrooms at Kenney's beach in Southold. First floor has a two story living room with huge fireplace and skylights. The dining room features a banquet size dining table and sliding doors that lead to an enormous deck with arched built in seating. Deck also wrought iron furniture and a stainless Weber grill. There is also an outdoor shower steps away from a door that opens into a mudroom. The kitchen has granite counters and brand new top of the line stainless steel appliances. Off the kitchen is a mud room with a washer and dryer and a full bathroom. The mudroom accesses the rear deck and garage to the side. First floor also has a large bedroom with a queen bed. Second story has bedroom with balcony facing rear and queen bed. There are two additional bedrooms with two twin beds in each of them and a full bath. There is wifi, cable, internet. Enjoy the most amazing sunsets at one

Located in East Hampton, New York, United States. Beautiful designer modern luxury home - steps from beach Stylishly appointed house, a quiet tree-lined street and mature landscaping equals relaxation in the Hamptons. This contemporary getaway is minutes from the water and is equipped with 3 bedrooms, 3.5 bathrooms and central air. Step outside to your large entertaining deck with good-sized heated pool and ample outdoor furniture for dining or lounging pool side. A beautiful walk to Sammy's beach or a short drive to the Ocean Beaches. The details make the difference in this luxury home:- Designer furniture throughout- Top of the line TV and surround system- Top of the line barbecue - Privacy- Automatic gating system- Sonos sound system throughout - easy to use- Outdoor shower- Modern Lighting system- Ample sun exposure on the deck - Lighting on the deck and illuminating the forrest- Alarm- Super-fast wifi- Light gym equipment in the basement or in mudroom (bench and free-weights)- Mudroom can also be fitted with massage table

Located in Southold, New York, United States. Charming, Historic Farmhouse close to restaurants, vineyards and beach. New to the Market this season! Charming historic 1909 farmhouse with 3 bedrooms and 1 1/2 baths and modern amenities. Beautiful enclosed porch, French country kitchen and new patio with grill, sectional, dining table, chairs, umbrella and fire pit. Drive to Orient Beach, Vineyard's and restaurants. 10 minutes to Greenport. 4 car garage and circular driveway. Permit #0654Check out a Video Walkthrough of our home https://www.youtube.com/watch?v=FnYGoIJrltY**Southold Township has minimum stay requirements and we aim to keep compliant with local laws. Please feel free to contact us to discuss your specific needs and we will try to accommodate a stay at our wonderful historic home.

Located in East Hampton, New York, United States. East Hampton Retreat Spacious, sunny house on a secluded acre beautifully decorated and described as 'pristine'. Heated pool/very large outdoor Hot Tub/Jacuzzi, Central A/C, wood burning fireplace, blocks away from beautiful, private Bay Beach on Gardiner's Bay as well as Cedar Point Park, a 600 acre preserve. Amazing celebrity filled yet extremely quiet neighborhood in Northwest Woods of East Hampton located about 5 miles to the town of East Hampton and a short drive to Sag Harbor.Brand new kitchen with large kitchen island, wine fridge, stools for breakfasting or chatting with the cook, Kitchen opens onto dining room and living room. Kitchen is well stocked with top-of-the-line appliances/cookware/knives) for cooking, serving, and entertaining.Living room is large and open with high ceiling and view through glass sliding doors is to pool, garden and Cedar Point Park beyond. All bedrooms have high quality linens. Towels are plentiful and in good condition.Porch in front of house with

Located in Shelter Island, New York, United States. Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located! Shelter Island is a unique place with incredible natural landscapes and gorgeous sunsets!Once you get off the ferry, drive to the end of a private road to find your oasis on a full acre of land where you will relax and enjoy the sun drenched backyard and pool with friends and family. Our home is designed to encourage you to spend as much time outside and includes a screened in sun porch perfect for reading and entertaining during sunny or rainy summer days. We have an outdoor fire pit for cool summer evenings, patio area with outdoor seating and a solar powered heater for the gunite saline pool! Please note our pool is open between Memorial Day to Labor Day each season.Inside our home, we offer 3 bedrooms upstairs and 1 bedroom downstairs. All linens and towels are provided with the rental. The upstairs has a completely private master bedroom suite which is open, airy and features a king sized bed with spacious walk

Located in East Hampton, New York, United States. Contemporary retreat on 1.4 wooded acres with an open floorplan and private... Ely Brook EnchantmentContemporary retreat on 1.4 wooded acres with an open floorplan and private pool in coveted East Hampton.4BR/3BALight and bright interior with vaulted ceilings and skylights, contemporary furnishings, and ample entertaining space with private pool and hot tub.Entering through the private gated drive, youll arrive at this extraordinary contemporary home that includes four bedrooms, three bathrooms, and 2,200 square feet of living space set on 1.4 acres of exceptionally private, wooded land. Vaulted ceilings in the great room offers a wonderful sense of space, while the fresh white walls and abundance of windows and skylights call attention to the verdant foliage of the property. In the living room, windows and sliding doors provide wraparound views of the property and an abundance of natural light. Here you will find a flat-screen TV, a wood burning fireplace, and a large sectional that a

Located in Sag Harbor, New York, United States. Luxury Home in Sag Harbor Immerse yourself in one of Sag Harbor Village's famous historical landmarks. Culinary celebrities frequented this landmark once known as the "Tomato Lady" farmstand. Tastefully appointed and updated by a local designer, this gem has 3 bedrooms, 2 baths, an eat-in kitchen, and a library/dining room. The patio adjacent to the kitchen, illuminated with string lights, is a perfect spot to unwind in the summer breeze and entertain into the night. Walkable to all of what Sag Harbor has to offer! Come!The property has a huge backyard that’s enclosed with flowering plantings throughout the season. There is a nicely sized patio with a dining table, eight chairs, two lounge chairs and a BBQ.There are two bedrooms upstairs, and one downstairs. The primary bedroom is furnished with a king bed and has an en-suite. The second bedroom has a twin bed and twin trundle. The third bedroom downstairs, faces the garden, and has a queen sized bed.Both bathrooms have a shower and ba

Located in Southold, New York, United States. Cute Cottage Apartment Near town, beaches and vineyards (WBH) Calendar NOT always up to date check for availability Beach Parking good at all Southold Town Beaches Pass INCLUDED free with rentalCome listen to the bands while tasting the local wines (See local vineyards and events) , Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of town In the heart of the North Fork Wine Country and beautiful beaches. We have a 1840's home with a furnished attached cottage available for weekend's, week or month rental. Cottage has small eat in kitchen, bath, living room and 2 bedrooms. One bedroom has a queen size bed and the other a full size bed. Separate entrance with own patio area and comfortable patio furniture. Comfortably furnished with Sat TV (Including HBO). Both bedrooms have center AC units. Beautiful property with century old lilacs and gorgeous perennial gardens. Ocean Beach

Located in Orient, Washington, United States. Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach Charming, updated historic farmhouse set on 1.6 acres in Orient Point - perfect for a large family vacation. Fenced in yard and deep woods at the back of the property create a quiet and private space. Heated saltwater gunite outdoor pool with hot tub and poolside outdoor kitchen with grill and stainless-steel sink. Spacious eat-in kitchen with dining room table and separate outdoor pergola perfect for entertaining. Spacious living room with wood burning fireplace and separate den for kids to play. Mudroom with full washer and dryer. Cross the street for drinks or dinner at Duryea's and the entrance to Orient Beach State Park (bike (10 min), run or drive into the park itself), 10 min walk to the beaches of Orient Point County Park, 20 min bike / 5 min drive to historic Orient town center and Truman's Beach (beach guest pass available). Town of Southold Rental Permit #724

Located in Shelter Island, New York, United States. Stunning Waterfront Estate House with 270 degree sea views on 7 private acres This stunning waterfront Estate House is a quiet paradise nestled in 7 private acres of nature on the pristine Menantic Peninsula. Enjoy strolls along the water’s edge or bask in the sun on the large plank stairs, which lead to a private, sandy beach area for frolicking, kayaking, and clamming. Marvel at magnificent sunsets nightly from the comfort of the seaside jacuzzi, or commune with hawks, herons and osprey in this peaceful nature sanctuary.Newly renovated as of Spring 2020, this is the first year the Estate is open to stay. Scandinavian beauty meets modern luxury in this elegant, uplifting home. Every room offers panoramic sea views. Cathedral ceiling and copious skylights make heaven and earth meet. Sun-filled, spacious living and dining area are steps from the water. Open, ethereal kitchen offers marble counters, sub zero fridge, Viking gas stove, electric stove, and two dishwashers. White oak floors

Located in Greenport, New York, United States. NOFO ESCAPE relax-swim-enjoy. Bachelorettes-Weddings-Family vacation Bachelorette, weddings and big party escape.Go fishing, boating, hiking, golfing, antique shopping etcwalk to town, walk to beach,walk to vineyard, walk to restaurantsEnjoy Greenport, named by Forbes magazine one of the 11 prettiest towns and villages in America.Take Hampton Jitney from Manhattan or LIRR.Take New London to Orient ferry from Connecticut.Use Long Island Expressway (495) or Northern State Parkway to drive from Manhattan, New Jersey, Brooklyn, Queens, Nassau

Located in East Hampton, New York, United States. Coastal woods respite, walk to beach Modern home short walk to gorgeous beach. One acre, wooded and secluded property. Gourmet kitchen, Viking stove/oven, Subzero fridge, sound system, Scandinavian furniture, WiFi, heated pool w/ safety fence (can be taken down upon request), outdoor showers, lawn (organic treatments, no toxic pesticides), BBQ, FrameTV, office, Tesla / EV charger. 15 mins drive to East Hampton Village, 15 mins to Sag Harbor. Pool open May-Sept. No discount requests please. Thanks!RR 21-1,241HMT23-665

Located in East Hampton, New York, United States. Upper Northwest Spacious Home - 10 minute Walk to the Beach! PLEASE CONTACT BEFORE BOOKING OTHERWISE YOUR BOOKING WILL BE CANCELLED. HOUSE DETAILS:Renovated in 2022, this bright, one-of-a-kind East Hampton home epitomizes the beauty of indoor-outdoor living in the Northwest Woods. Stunning amenities include multiple walls of floor to ceiling windows and an open floor plan that is ideal for entertaining. The main floor features an oversized living room and dining area with fireplace, a large kitchen with a stunning waterfall island that opens to a separate deck, a primary suite (king bed) with fireplace and full bath complete with a steam/rain shower, a junior primary suite (king bed) with Jacuzzi tub, and a separate half bath in the living room. The lower level offers two additional en-suite guest rooms (one has 1 queen bed, the other has 2 queen beds), an office/den/flex bedroom (with 1 queen bed), a media room with a large sectional and TV, another full bathroom and an amazing wet ba

Located in Sag Harbor, New York, United States. Stunning Waterfront 4 Bedroom Home with Pool, a Dock, an Acre of Land & a Boat This tastefully styled summer cottage is situated on the water with a beauitful dock, every toy you could imagine, and even provides a boat rental opportunity of a classic 1972 Boston Whaler. The gunite pool situated in acre of land in the back of the house, and a jacuzzi on the deck provides the perfect area for relaxing and escaping the bustle of the city. The pool is enclosed by a safety fence for kids - as we have three little ones running around at all times - and the yard includes a garden teeming with the East End's best summer fare. Whether you fancy throwing the ball, practicing yoga, hosting, fishing off the dock, or sitting around the fire pit - the home and setting is idyllic. The design of the interior feels like a beach cottage feel, and renters routinely remark on the style and appointments. The outdoor deck is where most guests eat every night during the summer and fall. We have an oy

Located in East Hampton, New York, United States. Butterfly House… surrounded by nature tranquility mid-century oasis Private beach access incredible biking private pool area, many areas to lounge on different balconies total privacy, Great architecture all new furniture all the amenities one needs, Great area to take incredible walks and nature.

Located in Bridgehampton, New York, United States. Hamptons House - 4 Bedroom House + 4 Bedroom Cottage with pool Ideal Location!! House is flawless and perfect! This 3 acre property has 4 bedroom and 3 bath full bathrooms. Located in the best part of the Hamptons. Comes with 4 bedroom cottage, with two bathrooms. Come stay at a beautiful Sag Harbor Home, where the beach and ocean are 10 minutes away. House is in perfect condition, and kept well. The house is set in a park-like property, very quiet and private, with no neighbors in sight, sits next to a reserve. 20 x 40 Pool, and pool area is beautiful. The Home is decorated with great furnishings. Very comfortable and easy living, very clean. All hardwood floors throughout. Large closets, balcony, and AC. All bedrooms have new bedding and towels. Living room has 20' ceiling - very open. Home has bright natural light. Kitchen has granite counter-top with all Viking stainless-steel appliances. Dining area for dinner. Three decks with dinner set and out-door gas grill, all new. 4 Bikes.

Located in Cutchogue, New York, United States. Tuscany in the North Fork - Spectacular Villa in the Midst of a Vineyard In the Heart of wine country, overlooking vineyard vines, enjoy your stay on the North Fork! Chef's kitchen, 4 spacious bedrooms, 5 bathrooms, gorgeous sun room leading out to a spectacular 40x25 heated gunnite pool with a slate patio and built in BBQ. Full basement with tv area, full bath, and entertainment space. Surrounded by North Fork award winning vineyards, renowned restaurants, farm stands, shopping and great beaches.

Located in Shelter Island Heights, New York, United States. TRANQUIL RESORT STYLE RETREAT WITH LUXURY GUNITE POOL 2 MIN FROM SANDY BEACHES This newly renovated sun-drenched Shelter Island retreat with an exquisite 21'x42' Gunite, wifi-enabled luxury heated pool is located in the tranquil Hay Beach area on a shy acre within close proximity to sandy beaches. A 1971-built ranch style charming house with mid-century, beach-chic modern touches, features an amazing outdoor entertainment space, surrounded by 4,500 square feet of decks and patios on all 4 sides of the house. The expansive 2,500 square foot stunning imported marble pool patio has beautiful ancient fossil inclusions, cool to the touch even on the hottest days, welcoming for lounging and relaxing in a beautiful and serene environment. A recently renovated open-plan kitchen with high end finishes and LG appliances, the interiors feature 3 bedrooms, 2 baths, a two-sided fireplace visible from the kitchen, dining, sitting area and living room. The master bedroom has a 3'x3' remote controlled

Located in Greenport, New York, United States. Updated and dog-friendly, close to seasonal activities with yard, & washer/dryer Modern on 9th Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Originally an old-time candy and soda shop this 1957 home is truly a charmer. Recently updated with modern touches, find yourself enjoying a beautiful vacation in Greenport, New York at this beloved home. Close to wonderful wineries, local beaches, lavender fields, pumpkin patches, and even holiday tree farms, there is an abundance of activities to enjoy regardless of the season! During your stay check out the Sparkling Pointe Vineyards & Winery (six miles), Pindar Vineyards (seven-and-a-half miles), Orient Beach State Park (less than 12 miles), and the Elizabeth A. Morton National Wildlife Refuge (43 miles). Shelter Island Ferry Greenport is less than a mile away and 67 Steps Beach is two miles away.Light, bright, and inviting, when you find yourself back at

Located in East Marion, New York, United States. Lovely North Fork Sea Captain's Home Town of Southold Rental Permit 0605 The Sea Captain's Home is a sprawling, well-preserved, 4-bedroom-plus Italianate Victorian, featuring large rooms, tall ceilings and striking detail, on a natural 3/4 acre property. Built in 1860, the house is a lovely combination of the gorgeous architectural detail of the time, and the modern amenities of today. Situated between Greenport and Orient, in the quiet hamlet of East Marion, this peaceful spot is surrounded by farmland, with open fields behind, and wild coastline minutes away. Greenport is a five-minute drive, and any number of local beaches, from the quiet sandy bay beach a half mile away, to the the more dramatic sound beach at the end of Rocky Point Road, can easily be reached by bike. Sep's farm stand, Angel's country store, the now-legendary lavender fields and the Hampton Jitney stop are all a short walk away.When you're back from the beach, vineyards, shopping, or from a great meal at one