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300+ Vacation Rentals · Southold
300+ Vacation Rentals · Southold
Lovely victorian home for the discerning vacationer.
Diamond upscale home with 4-5 bedrooms, full baths, 2 private decks, screened porch for dining, relaxing, formal dining room, full kitchen, private parking. Endless amenities, spacious home for the discerning traveler! Steps away to your own lovely private beach. Minutes to the most famous town on the east end for dining, shopping, entertainment, boating, kayaking, water skiing, jet ski, chill and relax by the beach. Spend the afternoon at one of the largest selection of vineyards. Wine...
This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefront is secluded from neighboring properties and is superb for swimming, boating and fishing. Swimming in Long Island Sound is just six blocks away at Kenneys Beach. Dine on the deck with a sunset view of the lake and then stargaze with no interfering city street lights. Cottage has two bedrooms accommodating up to four people, an all-electric kitchen with microwave and co...
Located in walking distance to the quaint Village of Southold and also the Hampton Jitney and LIRR. Close to tennis courts and public playground. Within a mile of beaches, farmstands, and vineyards. Extensive backyard. Perfect location to bike to all
Experience barn living. Open living plan with combined kitchen and living room. Two private seperate bedroom. Master bedroom is located in loft and second bedroom is located off of living room. Lots of skylights and beams. Freshly painted and decorated. Step out your back door to wide open space with a brick patio and deck with hottub, seating area, table, and gas grill. Interior wood burning stove adds ambiance and washer and dryer adds convenience. Barn is located behind my home. Prime...
Our comfortable house on the North Fork of Long Island has three bedrooms and 2 (website hidden) is located in a quiet neighborhood in Southold with a private beach looking out to Shelter Island.We have a water view from the deck.Has central air conditioning.
The home is very cozy and tranquil, in a great location. The home is open concept with a great room, including living room, kitchen and dining room. There is a cathedral ceiling in the great room. Guests will have access to bicycles, a kayak, wagon, fishing equipment, towels, linens, kitchen utensils, barbecue, wifi, 3 flat screen TV's, I pod/CD dock, a guest handbook and much more. The owner will greet the guest upon arrival. The neighborhood is very quiet and relaxed, with the historic...
Our peaceful, cozy home, built in 1910 with modern updates, is centrally located near vineyards, beaches and Southold town. Enjoy multiple patios, picturesque yard, large kitchen and family-friendly amenities. 1 mile from Goose Creek beach.
Sunny, charming 3 BR home with cozy character, ideal for entertaining and families. Hardwood floors, bright rooms, plentiful outdoor space. Bike ride to beach (1 mile), Southold town (1 mile) and creek access (1/2 mile). Less than 5 mins from some of North Fork's finest wineries and farms. Upstairs are 3 bedrooms, with 4 beds and room to sleep 7 comfortably, and full bath with glass block walk-in shower and vintage pedestal bathtub. Spacious downstairs with 2 sun-drenched living areas (inc...
Located on a bluff overlooking the Long Island Sound with it's own beach, stunning sunsets and panoramic water views, this newly renovated, spacious house offers a tranquil getaway in bucolic Southold on the North Fork of Long Island's Wine Country.
The Shorecrest beach house is located on a grassy bluff overlooking the waters of the Long Island Sound with its own private beach. The house has three bedrooms on the ground floor, one with Queen bed, one with a king bed and one with twin beds. The second floor is open plan with sitting and sleeping area with 2 twin beds; picture windows overlook the water. On the ground floor are two newly renovated full baths with shower and tub on the ground floor plus outdoor shower; a large living r...
Come and enjoy the water in all it's glory! Kayak, swim, paddlboard in the backyard in the freshwater lake or walk a block to the Sound to bathe in the cool waters of the Long Island Sound at Kenny's Beach! Sunsets every night.
The house is a 4 BR, with a pull out couch in the living room, sleeps 12. Master Bedroom has a king sized bed with a balcony overlooking the sound. 2nd BR has a full size bed on the floor perfect for a toddler. 3rd bedroom has a full size bed and 2 twins with windows overlooking the sound. Downstairs the bedroom has a double bed, 2 bathrooms plus outdoor shower. 2 person kayak, stand up paddleboard, propane bbq, outdoor shower, lots of beach accessories, umbrellas and toys, a wagon. no ...
Located just across a small street from a private beach in beautiful Southold, on the northeastern end of Long Island, NY, this wine country condo can be found on a huge private sandy beach. It is on the second floor of a condo complex which includes 42 units. Visitors from NYC, PA, Connecticut and Massachusetts can reach us in about 2 to 3 hours. The condo has 3 rooms and accommodates 6 people comfortably. The first room has a full size bed with table and chairs, Directv cable television,...
From a quiet, secluded property of woods and lake, swim, boat, fish, bike, watch the sunset, listen to the birds and frogs from our hammocks at our lovely and immaculate cabin on a half-mile freshwater lake, under a mile to a life-guard Sound beach.
With a new kitchen, stocked with staples, bright great room with fireplace and plenty of comfy seating, bedrooms with large windows to let in the sun and view, and 1.5 new bathrooms with unlimited hot water, a large gas grill, you have a terrific home base for your vacation adventures. Ceiling fans and bedroom A/C keep you cool; adjustable heat in every room keeps you warm. Use our pedalboat, kayak, rowboat, inflatables from our waterfront, and bicycle within just 2 miles to several winerie...
Waterfront 5 bedroom home / 2 baths --- 2 acres of land with a floating dock for a boat. Located on private road in Southold NY…. Beautiful Waterfront views of the water… hot/ cold outdoor shower...
Beautiful location on the water.... WiFi Town beach across street Peaceful and quiet with a bird's eye view of nature.
Lovely beach getaway close to wineries and steps from a private beach. Open, airy, modern house with a big fenced yard to relax in.
Newly decorated beach house near vineyards on the North Fork. Just steps from a private beach. Please note: Southold town has passed a new law requiring 14 night minimums for any short term rental. Please contact me if you'd like to discuss this. Three bedrooms, 2 baths and a huge yard—all the amenities you need to enjoy your summer vacation. Sleeps 7 comfortably in this house with central air conditioning. PLEASE NOTE: July and August are only available for full month bookings. No week...
Relax in a newly renovated 2 bed, 2 bath home, walking distance from the heart of Southold. Only a mile to Goose Creek Beach. After a day of sun and fun, unwind with a local bottle of wine and kick back on the porch.
Newly renovated ranch North Fork wine and beach country home with 2 bedrooms, 2 bathrooms. Perfectly located in walking distance from the heart of Southold on the picturesque Jockey Creek. Less than a mile from Goose Creek Beach and less than 2 miles from Founders Landing Beach and South Harbor Beach. Property sits on 1 acre of lush, grown in yard, guaranteeing privacy. Enjoy local award winning restaurants, wineries, shopping, and farms. The home offers central AC and heating, outdoor por...
Centrally located on the North Fork close to beaches, vineyards and the Village of Greenport. Walking distance from the Jitney and the LIRR in Southold. Stroll into the quaint town of Southold or to the playground and tennis courts at Southold School
Very spacious living space with luscious quiet yard. Centrally located close to town, shopping, farm stands, vineyards, local brewery, and beaches. Parking available. Close enough to walk to town but far enough away to embrace the serenity of the North Fork. Large deck and Yard Space. Very knowledgable of the ins and outs of the North Fork.
We are a family of 4 from Brooklyn that used to rent in the North Fork for years. A few years ago we realized that we were never really happy with our rentals. We wanted open living, modern (but yet comfortable and stylish) home which was close to all of our favorite wineries, farms and restarants - not too far from the village of Southold. Our home is absolutely spectacular and we try to use it as much as we can. For the days that we can't use it, we are happy to rent to good people that...
Centrally located, visit the Northfork Wine Country, the Hamptons, Jamesport, Montauk, Greenport or Orient Point. Small Dogs allowed! We have cable and WIFI internet service so bring your laptop and you can check your email!
This is a classic North Fork beach house that can accommodate 4 people comfortably. Rent this house and have access to a huge sandy beach at Founders Landing. Located in in the town of Southold, on the east end of Long Island, NY, this beach cottage is with in walking distance to the Peconic Bay side of the east end. Visitors from NYC, PA, Connecticut and Massachusetts can reach us easily. Our beach house has comfy sleeping arrangements. 2 bedrooms and 1 full bathroom and We welcome c...
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