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300+ Rentals · Southold
300+ Rentals · Southold
Southold waterfront with dock in quiet family friendly beach community. Recently renovated. Private community beach right down the street or jump off the dock during high tide. Enjoy all the North Fork has to offer: wineries, farm stands, boating, preserves, restaurants, and village shops. Greenport and Shelter Island are a quick drive or ride. Learn More
Amazing views. 2 bedroom, 1.5 bath cottage. Recently renovated, all new appliances. Wifi. Community beach, kayak, bicycles in the shed. Not at all. Family friendly. You will need a car.
Private new studio in a luxurious upscale home, new ceramic bathroom, beach community, and lush landscape. Greenport Village walking distance, board walk, marina, fine dining, casual restaurants, beautiful beaches, private beach steps away. "Complimentary bottle of local wine always at check-in" !! Available upon request: Beach towels, cooler, chairs, umbrella.. Wine Baskets, our own local wines, sparkling wines, cheese platters, special occasion specials and other requests. 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. Please ask the host for breakfast, lunch and dinner specials. Efficient Refrigerator, coffee maker, other cooking available upon request. Private entrance, stairway to a lush rose lined veranda. Welcome guests! My rental set in a lovely private community offering the discerning traveler some of the finest restaurants, spectacular beaches...
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...
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. 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...
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
Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen in this 2 bedroom, 1 bathroom cottage. Learn More
Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable bedrooms; one with queen bed, the other with two twin beds both have ceiling fans. All are tastefully appointed and include linens. Our bathroom is also brand new with stone and marble tile, a cathedral ...
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! 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 an...
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...
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. Learn More
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...
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...
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...
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 Learn More
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.
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. Learn More
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...
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...
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...
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