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300+ Vacation Rentals · Southold
300+ Vacation Rentals · Southold
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.
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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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.
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...
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.
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.
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...
Great value in Southold on the North Fork of Long Island. Very spacious, private entry suite, with large bedroom, large living room, brand new bathroom, cable tv and CAC. Minutes from wineries with beach rights. Seasonal access to in ground pool.
We can provide winery tours for a modest fee. The Hampton Jitney stops .4 of a mile from our home. We can pick you up and provide transportation for a modest fee. This apartment requires a 2 week minimum rental by Southold Town statute. There will be no exceptions. The weekly rate is $275 with a 2 week minimum.
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.
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...
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.
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.
Lovely 3 bedroom house across street from water in Southold, Long Island. Enjoy the tranquility of the country and a view of Hashamomock (Arshamonaque) Pond - an inlet of the Bay. Located on a peaceful dead end street, a short walk (2 houses down and across street) from the public boat access of Hashamomock Pond - great swimming, wildlife viewing, fishing, and boating. We are walking distance from Farmer Joe's Farm Stand, a 5 minute drive from Southold's Sound Beach, and less than 10 minutes ...
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.
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...
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
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Spacious 4 bedroom, 3 bathroom home in the heart of Wine Country on Long Island’s North Fork. Just steps to bay beach. Short drive to Main St. & Greenport. All seasons incl Winter Wine wknd, girls' getaway or bachelorette & wedding parties.
LOCATION: •Southold, North Fork of Long Island. •Antiquing, fishing, kayaking, bike riding, golfing or just lounging on the beach. •Just minutes from Greenport Village •Short drive to Tanger Outlets and Splish Splash Water Park DETAILS: FIRST FLOOR •Bedroom 1 – Queen-sized bed with en-suite Bathroom 1 with tub, also sitting room with skylight •Bedroom 2 – Two twin beds, bay window. •Bathroom 2 – Full bathroom ...
A great modern open floor plan . Gourmet kitchen, fire place Hot tub, pool, outdoor shower . 4 bedrooms , 3 baths. All high end renovation. Chic, loft like living space. Outdoor space is an oasis. 3 houses to a private beach Plus centrally located to all the vineyards on the east end.
All brand new completely renovated house. Every amenity Imaginable. Guests can walk to the beach. Guests can enjoy in the summer months ,a beautiful pool and outdoor shower. Hot tub all year. Close to all vineyards on the north fork. As often as they would like. Beach, vineyards, restaurants, boating, nature, gorgeous landscape. Easy Fall/ winter enjoy restaurants and all vineyards. The house has a beautiful fire place and hot tub for year round enjoyment. Cable surround sound flat sc...
**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.
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.
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...
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!
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...
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