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300+ Rentals · Southold
300+ 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...
**Note our Legal Multi Family property is NOT effected by the new Minimum 14 night rental law. Law applies to SINGLE family residences. You are free to rent at the White Blossom House with only a minimum 2 - 3 night stay.** 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 furniture. 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...
Beautiful mid-century modern 4-bedroom home with pool set directly on the water. Incredible sunset views, bike to beaches, farm stands and vineyards. Kayak right off the lawn or head to the basement ping pong table. Basement can easily sleep additional kids, guests, etc. Learn More
You'll have access to the whole house - huge front yard, large backyard that slopes directly down to the water, the pool, the playroom in the basement with a ping pong table....there's no shortage of entertainment options here. We love the North Fork and are happy to offer tips, favorite spots, and any assistance necessary during your stay. The house is directly on the water, close to incredible vineyards, great restaurants, beaches and a natural preserve with trails. We are equidistant f...
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 ...
Waterfront with private beach 2Bed 2Bath condo, full kitchen, balcony and pull out queen size living room bed, fits 6 people Learn More
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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 ...
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. 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. Greenport Annual Maritime Festival Sep 25 - 27, fantastic weekend you don't want to miss ! Efficient Refrigerator, coffee maker, and grill available upon request. Please ask the host for breakfast and lunch special request. Private entrance, stairway to a lush rose lined veranda. Welcome guests! My rental set in a lovely private comm...
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14 day minimum (prefer 1 month). Private pool area, cathedral ceilings, indoor/outdoor living on 3/4 of an acre. Less than a mile to village and beaches. Charming One Woman winery down the quiet street. Southold Cellars down the other street. Learn More
14 day minimum (prefer 1 month). Spacious, private, quiet, has a pool and huge deck, and is 1 mile from the Bay and the Sound. This is a three bedroom, 3/1/2 bath with cathedral ceilings on the most beautiful street in Southold. 1 mile from Southold village and 3 miles from Greenport village. Jitney/LIRR stops in Southold. Large kitchen with island. Counter flows into great room, pool area and upper deck off kitchen. Lots of windows and french doors. Bottom floor separate suit/bedroo...
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...
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...
Beautiful house surrounded by trees, but only a 10 minute walk to the beach and closest vineyard. Large lawned garden and covered porch - perfect for night time get togethers. Double height light-filled reception and 4 bedrooms, 2.5 baths Learn More
If you want to have wooded seclusion but be walking distance (10mins) to the beach, and be able to accommodate a group of friends for bbqs on the lawn, you'll enjoy what my home has to offer. The home comfortably sleeps 8 in 4 double bedrooms. 3 bedrooms are en suite on the second floor. The 4th is on the first floor next to a half bath. The home has a back deck with propane bbq, and a large covered porch to enjoy bug-less cocktails in the evening! Steps down from the deck land you on a ...
Cedar shingle cottage has large deck with steps down to own private beach. Magnificent views of setting sun. 2 bedrooms can sleep up to 8. Modern kitchen has dishwasher. Updated bath. Ceiling fans and air conditioners for cooling. WiFi, cable. Learn More
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...
SUN FILLED CONTEMPORARY HOUSE ON THE BEAUTIFUL EAST END OF LONG ISLAND. STEPS TO PRIVATE BEACH, MAGNIFICENT WATER VIEWS, GREAT SUNSETS. 3 BEDROOMS, 1.5 BATHS, MUSIC ROOM WITH STEINWAY GRAND PIANO. CENTRAL AC, FIREPLACE. Learn More
Beautiful light filled rooms. An open plan with livingroom/diningroom and kitchen. There are two bedrooms on the main level, one with a queen size bed and a smaller room with a double bed. The upper level has one bedroom with a double bed. There is a full bath on the main level and a 1/2 bath on the lower level. The music studio with the piano is on the lower level. During the summer months the outdoor shower has hot and cold water. Close to wineries, all water sports and boating, hiking...
GREAT OPPORTUNITY TO VACATION ON KENNEY'S BEACH AND ENJOY THE WINERIES ON THE NORTH FORK! AIRY, OPEN FLOOR PLAN & HUGE DECK. 4BEDRMS WIFI & CABLE. WILL PROVIDE PERMIT FOR ALL BEACHES. Learn More
Beautiful, airy open floor plan. High ceilings. Huge deck. All beaches in town of Southold. Access to award winning wineries! Wifi and cable. upon request Best beach on the North Fork! Train taxi bus vggvj All beaches in town of Southold. Access to award winning wineries! Wifi and cable. upon request Best beach on the North Fork! Train taxi bus vggvj All beaches in town of Southold. Access to award winning wineries! Wifi and cable. upon request Best beach on the North For...
The cottage is an original 1930 cottage with few changes. The appliances are new. It is on Hashamomuck Pond which is a salt water tidal lake that is connected to the Peconic Bay by passing under a railroad bridge. There is snapper fishing in the pond as well as swimming. The Town Beach is across the street. There are many restaurants, wineries and farms very close. There is a row boat for use as well as an adult bike & a kid's bike. Learn More
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