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Long Island Cottages

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    Travellers to Long Island are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    34 Matching Rentals in Long IslandView all 426 rentals
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    Cutchogue Beach Cottage1 / 18
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Beach Cottage in Wine Country ,Walk To private bea1 / 20
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Beautiful French Country Cottage1 / 11
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Unique  English Country Cottage1 / 10
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2016
    The house was beautifully maintained inside and out with a fantastic outdoor area to sit chill and enjoy barbecues and watch the local wildlife with a pretty rocky road beach a...
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    About this property
    . North Fork- East Marion- Charming unique twin cottages with cedar roof and historical significance. Each cottage is new and elegantly appointed. Wide plank flooring and knotty pine doors. Complete kitchen with granite counters and dishwasher. New bath with Italian tiles. Central air...
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    Location Information
    East Marion, North Fork 11939
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    North Fork cottage getaway with private beach1 / 26
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2016
    The charming photographs of this lovely rental conveyed the atmosphere we wanted as a base for exploring Long Island. The chief purpose of our visit was for my son's wedding...
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    About this property
    Four bedroom/2 bathroom cozy cottage located in the heart of the North Fork. Offers 3 bedrooms and 1 bath in main house with separate guest quarters including guest room loft and private bath. Includes outdoor shower, firepit, large bbq with fridge and outdoor dining with fireplace area. Centrally...
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    Mattituck, North Fork 11952
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    North Fork Beach Cottage in  New Suffolk1 / 19
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Grill
    • Air Conditioning
    • Patio
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2016
    I stayed at the Farmhouse Beach Cottage over July 4th and my friends and I instantly felt at home at the thoughtfully set up and charming cottage. Just minutes walk from the...
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    About this property
    Short walk to the most gorgeous bay beach, restaurants and marina. This adorable spotless 2 bedroom beach cottage sleeps 2-5 people and has a fully equipped kitchen with dishwasher, gas stove/oven, refrigerator with freezer, cozy living room with sleeper sofa and plenty of seating, tv, cable,...
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    New Suffolk, North Fork 11956
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Patio
    • Waterfront
    • Grill
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An ideal spot for a comfortable, peaceful beach vacation. Our charming, renovated cottage is located in Lonelyville, on Fire Island a short drive or train ride from New York City. If you've never visited Fire Island you're in for a treat. Close to the city yet a galaxy away. There are no private...
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    Fair Harbor, Fire Island 11706
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach House In Wine Country; Huge Sun Room1 / 16
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2015
    An absolutely stunning and beautiful home. Clean, comfortable, fully updated, this house is perfect for peace and relaxation. The bright and spacious sun room is perfect for...
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    About this property
    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...
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    Southold, North Fork 11971
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    • Porch
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A renovated home in the heart of the North Fork near the beach and several wineries. Please inquire about weekends, weeks or monthly/summer rental for 2015. Sleeps 8 Enjoy a bright renovated home with 12 skylights, cathedral ceilings and entirely new furnishings only ¼ mile to Cutchogue harbor and...
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    North Fork, Long Island 11956
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ocean Front Cottage Montauk for rent1 / 25
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Air Conditioning
    • Patio
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2017
    This was a small cottage with a spacious feeling. The ceilings were high and it was the perfect size for 4 people. We were able to cook breakfast everyday and it had most of the...
    Reviewed 29 August 2017
    great location. close to everything. very family friendly. very clean, BBQ, outdoor shower as well as 1 full bath and 1 ½ bath. I would recommend this to my friends.
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    About this property
    It is a 1000 sq foot cottage which is private, surrounded by hedges with the master suite, kitchen, main room and decks all over looking the ocean. Very warm and cozy, with wood beam ceilings, modern kitchen with all new appliances including dish washer. This cottage has been in our family for...
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    Location Information
    Montauk, Hamptons 11954
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cottage by the Sea1 / 5
    (6)Average
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Balcony
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2016
    Great location! Cottage was also very clean and well kept, perfect for our family beach vacation. Will definitely go back
    Reviewed 30 July 2016
    The cottage was very clean, well equipped and inviting. The location was terrific, only a block from the beach and town. We enjoyed the open floor plan and the lovely yard...
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    About this property
    This newly renovated cottage in the heart of Montauk is 1000 feet from the ocean beach. It is a free standing cottage with a large back yard for entertaining. It has been in our family for over 70 years. It has central heat and air, with hard wood floors and modern. It is located between the...
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    Montauk, Hamptons 11954
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seasonal rental within a 5 minute walk to private beach, ten minute walk to Giorgio's. 5 minute drive to local horse riding farm and ten minutes drive to local north fork wineries. 10 minute drive to downtown Riverhead, Long Island rail road, outlets and restaurants....
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    Baiting Hollow, Long Island 11933
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Housekeeping Included
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1 Night stay is available. Please inquire negotiable rates for longer stay. BOOK 2 NIGHTS AND STAY 3RD NIGHT FREE up until May 1st. (Excludes Free Fri or Sat nights.) Each season brings fun festivities! Seasonal rates reduced, please inquire to negotiate! Fenced in backyard. Minutes from Hampton...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage is in the perfect spot. Go to the everything. It has 1 bedroom with a private deck. It's wonderfully cozy and a perfect place to come back to after adventuring around town or just lounging on the beach. Southampton Village is just 3 Cooper's Beach is 6 minutes. This cottage is...
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    Southampton, Hamptons 11968
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • DVD Player
    • Waterfront
    • Parking
    • Grill
    • Hot Tub
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique country cottage is situated on a spring-fed fresh water lake one block from Kenney's Beach - a sandy Long Island Sound beach staffed by Southold Town lifeguards. Designed to maximize the beauty of its pristine surroundings, the entire back of the house has French doors opening onto a...
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    Southold, North Fork 11971
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Central Heating
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This vacation rental cottage in the Sag Harbor area of the Hamptons is a cozy getaway with 3-bedrooms and 2-bathrooms, comfortably accommodating up to 6 guests. Newly renovated throughout, the property upholds the historic beach cottage charm of the Hamptons! Close to North and South Hampton with...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Balcony
    • Patio
    • Internet Access
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This rustic one bedroom is located directly on the newly sanded beach. This is a true beach house. This home has a brand new kitchen and outdoor hot/cold shower! This home sleeps 5 people with sofa bed and cot. Everything is fully furnished with towels, linens and everything you would need. The...
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    Wading River, Long Island 11792
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Patio
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the best of both worlds! Wake up and take your kayak or stand up paddle board across the street and out in the beautiful N. Sea Harbor & then head into nearby Southampton village for a nice relaxing lunch. Finish the day by soaking in the hot tub with a glass of wine & enjoying the...
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    Southampton, Hamptons 11968
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Terrace
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fire Island is a 35mile long barrier island located just off the South Shore of New York's Long Island. It is an island of many diverse communities. The house is located in a community called Lonelyville, one of the oldest on Fire Island. There are no cars permitted on Fire Island, the house comes...
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    Fire Island, Long Island 11706
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chic Sunny Private 2 bedrm Cottage (93 miles frm NYC) that step out on to your own secluded patio w/outdoor furniture + gas grill for easy BBQ meals. Cottage guests hv their own gate entry to the pool. You are minutes from World Famous Cooper's Beach, convenient to Village Shopping +Restaurants....
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Ocean Views
    • Waterfront
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    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful Sag Harbor VillageWaterfront Cottage for Rent 3 bedrooms, 4 queen size beds , 1 1/2 baths, A/C, Screaming Water views, multi level Decks, Private Sand beach, with Kayaks and fire pit. All inclusive utilities, Maid service (weekly) and wonderful clear Water and sandybeach. Grill,...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a newly renovated 3 bedroom cottage in the beautiful historic district of East Marion. Two new full bathrooms, beautiful full kitchen & dining room, den & living room. Bedroom #1 has 1 queen bed, bedroom #2 has 1 full bed and bedroom #3 has 1 twin. There is a sofa bed in the living room...
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    East Marion, North Fork 11939
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Parking
    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enter a world of tranquility and surround yourself with the beauty of nature! Decorated with an eclectic mix of antique and contemporary furniture, the home has three bedrooms, one bath, dining room, living room with large flat screen tv, sunroom with seating and dining area. Kitchen is remodeled...
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    Peconic, North Fork 11958
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is right on the sand, just a block away from a beautiful, uncrowded ocean beach in one of the world's most famous resort communities. Clean and comfortable, there is an upstairs deck off the living room and a downstairs patio off the eat-in kitchen, three bedrooms, two full bathrooms, a...
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    Amagansett, Hamptons 11930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Patio
    • Waterfront
    • Washer
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage can only be rented when its' bigger neighbor (the Luxury Beach House) is not rented. Available for monthly inquire. Brand new affordable beach cottage located directly on the beach! This adorable 1 bedroom beach house is perfectly located right on the beach, with a large patio, gas...
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    Wading River, Long Island 11792
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Water Mill, Hamptons 11976
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Terrace
    • DVD Player
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very private newly renovated cottage can accommodate 2 adults and is tucked away in corner of gated property South of the Highway on one of the prettiest Village Lanes with close proximity to shopping, dining, and village beaches. Cottage overlooks the pool and flowerbeds, has a large covered...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming, private, 2 story cottage with outdoor balconies. 'Treehouse' feel with great wooded views. Queen bed, one loft bed, full bath, hardwood floors on second floor. Sitting area, twin bed on first floor with washer/ dryer. Covered balcony with gas fire ring, warm and cozy! Amazon / Netflix...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This private and quiet waterfront cottage is the perfect Hamptons retreat for one or two people. A short drive to the ocean beach or Main Street in the village for strolling and dining. Located near Southampton Village, the cottage is convenient for wine tasting excursions, antique hunting,...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Balcony
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom waterfront cottage is a perfect family getaway. Located in a small beach community between Southampton and Sag Harbor, it is surrounded by water - from the dining room you look right out onto a serene lake, from the first floor you can see both lake and the bay beach. You are only a...
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    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 10 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Ocean Views
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Getaway to this charming Cottage on the water with spectacular views!! 3 Bedrooms & Baths in the main house with a separate guest cottage with Bedroom, Kitchen & Bathroom. Heated water front Gunite Pool, Hot Tub, Dock plus Kayaks & Bikes. Close to the village of Southampton, beaches and all the...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 10 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fully renovated cottage is perfectly located just one house off the Great South Bay & only a 2 minute walk to town. Sunny & bright, freshly painted with H/W floors. The well equipped kitchen has a breakfast bar and new tile floor. The dining area seats 6 comfortably. The 2 sweet air...
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    Ocean Beach, Fire Island 11770
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Grill
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two bedroom cottage with vaulted ceilings set on a double lot, last house on a dead end quiet road with a pond and a nature preserve across the road. Lots of outdoor living/dining space. Outdoor shower, gas grill, herb/flower gardens, washer/dryer. 5 minute walk to private neighborhood sound beach...
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    Location Information
    Montauk, Hamptons 11954
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This quaint 2-bedroom, 1-bathroom vacation rental cottage comfortably sleeps 6 and is sure to become your home-away-from-home on the South Shore of Long Island. Huge trees, blooming bushes, and lush green grass surround the property, providing a serene escape from the hustle of everyday life....
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    Location Information
    Bellport, Long Island 11713
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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