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300+ Vacation Rentals · Southold
300+ Vacation Rentals · Southold
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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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...
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...
**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...
Our three bedroom, one bath ranch is fully equipped for your stay--bicycles, beach umbrellas and barbecue included! We are a short walk to the beach and close to all the vineyards. 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...
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...
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 ...
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...
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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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.
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...
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...
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 ...
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. Learn More
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...
Don't miss out on this cozy bright renovated waterfront North Fork home, surrounded by nature. Spend the off season with us. Relax by the fireplace and enjoy the privacy. And book now for summer. Filling up fast! Learn More
Enjoy sunshine year round and abundant flowers in season. Join us at our three bedroom one bath renovated house. Private waterfront. Stone fireplace and central AC. Beautiful hardwood floors and custom light fixtures. Open and airy. Fully stocked kitchen with 5 burner stove, stainless steel appliances and custom built island. Large deck and great outdoor furniture. Nice selection of book and games. Access to both dock and pond and LI Sound, block away. Semi private Golf Course clo...
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
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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.
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