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Long Island Cottages

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    Travellers to Long Island are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    24 Matching Rentals in Long IslandView all 517 rentals
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    Beautiful French Country Cottage1 / 23
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Charming Bay View Cottage1 / 19
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Unique  English Country Cottage1 / 22
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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 July 1, 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
    Beech Tree Cottage1 / 15
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Shared Garden
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 18, 2018
    With a full kitchen and living room, outdoor terrace and perfect so-close-you-can-walk-to-town setting, you will be so happy you snagged this spot! I’m picky, and I know what’s...
    Reviewed August 7, 2016
    Spent two nights at Beech Tree with my husband and grown son. Cottage is located within walking distance of town, in a nice residential neighborhood. Kitchen is well stocked, we...
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    About this property
    Beech Tree Cottage is a charming two-bedroom, one-bath guest cottage conveniently located in the historic district of Sag Harbor, NY - a 5-minute walk along the waterfront to Main Street and the center of the village. The beach is a short drive or bike ride away. The owners are full-time residents...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Lakeside Cottage, Walk to Beach. Beautiful Sunsets1 / 5
    (1)Excellent
    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
    Reviewed August 5, 2019
    We have staying at this cottage for many years and immensely enjoy the peace and quiet surrounded by the gorgeous views. We also love all the improvements over the years.
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    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
    Cutchogue Beach Cottage1 / 18
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • Air Conditioning
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 2016
    We had a very happy stay here. Contact with Julie was first class, the house is very tastefully decorated and comfortable. It is ideally situated to explore further but has...
    Reviewed August 8, 2016
    We so enjoyed our time here. You really can't find a more homey cottage and the close proximity to the great beach and scenic hilltop playground was tops. Julie was wonderful...
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    About this property
    Cutchogue Beach Cottage on the North Fork of Long Island. It has 2 bedrooms with queen sized beds and there is a sleeping loft appropriate for children over 9 years old (one queen sized bed and one twin). Deck and backyard with gas grill, outdoor picnic table, fire pit, and tire swing. Brand new...
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    Cutchogue, North Fork 11935
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    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 July 8, 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
    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
    Charming Cottage1 / 17
    (1)Excellent
    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
    Reviewed 2 weeks ago
    Absolutely loved our stay here. Beautiful spot, very peaceful and the flat was so well stocked for our stay. Thank you Leeanna
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • 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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    Location Information
    Fair Harbor, Fire Island 11706
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    The Victorian Seasons Cape1 / 34
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 5, 2018
    Had an Amazing stay .lovely grounds . Fell in love with the Gazebo and great hospitality. Very accommodating staff . Highly recommend.. enjoyably stay - Walking distance to a...
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    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 queen and bedroom #3 has 1 twin. Located close to beaches, ferry, Jitney...
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    Location Information
    East Marion, North Fork 11939
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    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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    New Suffolk, North Fork 11956
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    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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    Location Information
    Fire Island, Long Island 11706
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • 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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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Terrace
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For those seeking a peaceful, quiet, zen-like place to spend their vacation or honeymoon, 'The Shelter Island Hideaway Beach Vacation Cottage' is the home for you. The luxurious, waterfront 2-bedroom, 1-bathroom vacation rental cottage offers 1,125 square feet of sheer Caribbean-style elegance....
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    Shelter Island Heights, Shelter Island 11964
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
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    • DVD Player
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend a serene weekend with friends at this beautifully appointed 2-bed, 1-bath vacation rental cottage in East Hampton, NY. The home has an idyllic nature to it thanks to the shingle-style architecture, multiple outdoor seating areas, English-style flower garden with fresh herbs, and the elegant...
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    Location Information
    Springs, Hamptons 11937
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Wi-Fi
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    • Waterfront
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    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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    Southampton, Hamptons 11968
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
    5 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Place In The Sun This super bright and beach-themed home is located in the Ocean Beach Villiage on Fire Island and only two-hundred feet from the water. Each bedroom is fitted with twin beds with the exception of one room that has a full bed as a bottom bunk so there is room for the whole family....
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    Location Information
    Ocean Beach, Fire Island 11770
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 13
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely Elevated Home close to Smith Point Beach. Panoramic Water Views From The 2 level Deck. Great Area For Fishing With Access to 2 Marinas locally. 1 Bedroom Home With An Open Floor Plan including a loft. The Updated Kitchen Offers new appliances with lots of counter space. Full bath...
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    Mastic Beach, Long Island 11951
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Hot Tub
    • Cable/satellite TV
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    • 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
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
    About this property
    ** Please note that the homeowner lives on site, in a completely separate unit, and may be present during your stay ** Explore the oceanfront city of Long Beach from this 1-bed, 1-bath vacation rental cottage that sleeps 2! Located only steps away from the boardwalk and three blocks from the train...
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    Long Beach, Long Island 11561
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    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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    Montauk, Hamptons 11954
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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