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1000+ Rentals · Southold
1000+ Rentals · Southold
Our studio waterfront escape provides the perfect sunny setting for a weekend retreat all year round or a lingering vacation. Nestled on a lake like bay setting with beautiful lawn, yet with access to long island sound a block away. Learn More
Enjoy sun year round and beautiful flowers in seaon while you are surrounded by nature in our waterfront private studio cottage with new full bathroom, kitchen and flooring and cathedral ceilings. Cozy furnishings and fully stocked kitchen. Original mosaic mirrors and local artwork on display. Outdoor area with beautiful view over pristine Ashamamoque Pond to private preserve. Enjoy the idyllic setting with sightings of osprey, egrets and swans. Fishing in the bay and access to private...
Welcome to my incredibly cozy Southold cottage. Located steps to the Peconic Bay, village of Southold and a short lovely bike ride to the beach. This 2 bedroom 1 bathroom home has all you need for a memorable vacation. Learn More
Located off a private gravel road overlooking the Peconic Bay, tucked away on 1.5 acres providing ultimate privacy. The large outdoor screened furnished porch provides the ultimate relaxation while enjoying the sunset. The spacious furnished backyard is ideal for grilling, playing sports, lounging on the hammock or listening to the birds. Guests have access to 2 bicycles, charcoal grill, fully stocked kitchen, fresh linens, cable TV, wireless internet, CD/Ipod player and books. Washer / D...
2 private upstairs bedrooms with microwave, fridge and shared bathroom. 4 beds. Views, A/C, heating and Internet with TV access. 5 min. walk to beach. Quiet street. Deck/bbq access. 10 min. to wineries and Greenport. 20 min. to/from Orient Ferry. Learn More
Exclusive use of the upstairs area--2 bedrooms, with 2 beds in each. Private. Views front and back. Weekends April thru November are 2 night minimum stay. We will consider single night stays depending on availability. Deck with BBQ, garden, living room and kitchen. Hosts will be present on property during your stay. Join us for coffee and a chat or find a private place to enjoy the morning. We have two Golden Retrievers and a cat. Quiet, tree lined streets and it's walking distance to a ...
Clean, bright 3 bd/1 bth. 5 minutes to vineyards and the historic seaport town of Greenport. Walk to Kenny's Beach-- we have beach chairs, towels and a wagon to haul your cooler. Bicycles included! Learn More
This is our pretty three-bedroom ranch-style cottage, fully equipped, one block from Kenney's Beach; spend the day in the sand or visit the vineyards, Greenport, Shelter Island--this house is central to everything. A short walk to the beach, bike or drive to vineyards. Bike into Greenport and take the ferry to Shelter Island! Newly furnished and freshly painted, this home is immaculate. Wifi with booster, landline telephone, television with DVD player, washer and dryer, dishwasher, mi...
Private new studio in a home, new ceramic bathroom, beach community, and lush landscaped property. Minutes to Greenport, marina, delicious restaurants, beautiful beaches, boardwalk, ferry to Shelter Island and CT, private beach steps away. Learn More
New private studio offers comfort, cable, Wi-Fi, luxury and privacy along with the gorgeous surroundings, and off street parking w/separate entrance. Private entrance, stairway to the veranda among roses, gardenias and hydrangeas. Welcome guests and will be available if needed. Secure safe neighborhood and home. Lovely private community offering the discerning traveler some of the finest restaurants, beaches, entertainment, golf, and wine tasting on the east end of New York. Wine tasti...
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. Learn More
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,...
In the heart of Long Island wine country and beautiful beaches we have an Historic Inn built in the 1830's that has been carefully renovated to retain its old time feel Each cottage/unit has 2 bedrooms each with a double bed and patio. Come enjoy! Learn More
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 wi...
What I love most about my house is the closeness of nature around you. In the morning you are greeted by the sounds of all different kinds of birds and looking out of the kitchen windows toward the lake you will often see deer and other wildlife. Learn More
This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Barbecue and dine in the spacious backyard with a sunset view of the lake. Stargaze with no interfering city street lights. House has two bedrooms and a queen size sofa bed a...
A cozy beach house within minutes to lovely beaches. This cottage has 3 bedrooms and a sleeping loft. An outdoor shower is perfect for cleaning up after the beach followed by cocktails on a large deck or screened porch. Learn More
The spacious outdoor deck and screened in porch allow guests to take full advantage of their beautiful surroundings. The cottage is less than a mile away from a gorgeous public beach. We are located just two doors down to offer any assistance if needed. Located in the heart of wine country, this cottage offers plenty to do for children and adults alike. The home is just a few minutes walk from the beach and a short ten minute drive from the seaside town of Greenport. Several buses and t...
Ground floor master suite with private bath and separate entrance off a beautiful patio and large country backyard. Amenities such as WiFi, flat screen TV, A/C, Jacuzzi and use of private pool make this an ideal get-away spot! Learn More
Guests have access to nearby bay beaches, minutes from quaint towns and wineries galore. Interaction will vary- hosts will not always be available depending on schedule. The neighborhood is very quiet surrounded by several acres of nature preserves- close to town and beautiful bay beaches. A car is necessary, although beach is within walking distance. We have three wonderful cats.
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. Learn More
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...
Beautiful home on gorgeous tree-lined street on the North Fork of Long Island. Near to Greenport, Mattituck, Cutchogue, Orient, vineyards, beaches, farm stands and golf courses, although sparkling pool and sprawling front porch may keep you at home! Learn More
A very spacious house, 4 bedrooms, 4 bathrooms, dining room, sitting room, large kitchen, large and gracious front porch, swimming pool, large family room with ceiling fans, two fireplaces. Bedrooms on second floor are air conditioned. Very simply and tastefully furnished. Walking distance to charming town of Southold, 5 miles to Greenport with its quirky shops, movie theatre and carousel for kids, many farm stands nearby, famous Long Island vineyards, much more. We are available at all t...
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. Learn More
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...
Well laid out beach bungalow just a few yards from the water, and a 5 min walk to the town beach. Large yard, spacious living room, large master bedroom (14x18) with two smaller bedrooms. Very functional kitchen, screened in porch and second full bth Learn More
Idyllic retreat in North Fork beach and wine country. Quiet and peaceful, at the end of a private road, our charming, renovated 1830's farmhouse has complete privacy. Hammocks, outdoor fireplace, bikes, and kayak available. A bird lovers' paradise. Learn More
Idyllic writers retreat- quiet, peaceful, no car needed. Our renovated farmhouse is nestled in the woods off the Main Rd, so you get the country feeling and a lot of privacy, but can walk to restaurants, shops, grocery store. Bike to wineries and beach (Long Island Sound or Peconic Bay). From NYC you can take an express bus or train and walk to the house! After a brisk walk or bike ride sit in front of the roaring fireplace. Talk to us about a monthly or seasonal winter rental at a reduce...
Newly decorated beach house near vineyards on the North Fork. Just steps from a private beach. 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 weekends or week-long stays during those months. RATES FOR 2015: $2,500 - Weekly Rate $8,000 - Monthly Rate $8,500 - August, to include Labor Day $375 - Dai...
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... Learn More
Beautiful location on the water.... WiFi Town beach across street Peaceful and quiet with a bird's eye view of nature.
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