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Cutchogue Vacation Rentals

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    All 24 Rentals in Cutchogue
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    Cutchogue Beach Cottage1 / 18
    (9)Excellent
    Cutchogue
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Cutchogue
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cutchogue
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Cutchogue
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A new Fleets Neck home( May 2017), 2 blocks from Wickham Creek and a 10 minute walk to a lifeguard protected town beach and park. Beach parking permit supplied. Enjoy great restaurants and wineries near by. Sit on the covered front porch and commune with the wildlife while enjoying morning coffee....
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    Cutchogue, North Fork 11935
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cutchogue
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience Long Island's vibrant North Fork wine country like a local when you stay at this charming 'Vintage Cottage.' Nestled in the sought after beach community of Nassau Point in the heart of wine country, this 4-bedroom, 1.5-bath vacation rental for 10 is the perfect place for your Cutchogue...
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    Cutchogue, North Fork 11935
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    The following rentals are within 5 miles of Cutchogue.
    PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES1 / 17
    (2)Excellent
    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Central Heating
    • Balcony
    • Grill
    • Washer
    • Terrace
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 2016
    What a lucky find. This home has everything - location, setup and an owner to gives you complete backup for your holiday break.
    Reviewed September 24, 2015
    We had a wonderful time at Hickory House. The location in Southold is perfect for visiting the beach, wineries and farmers markets as well as Greenport and Mattituck. The home...
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    About this property
    3 bedrooms, 2 1/2 baths, sleeps 6 private Pristine, year round, vacation getaway, within 5 minute walk to two white, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home....
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    North Fork cottage getaway with private beach1 / 26
    (1)Excellent
    Mattituck
    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southold, NY Beach Cottage, Minutes walk to Beache, Farm Stands, Wine, Shopping, Let us know your dates! BI - Weekly Rental - Bring the Dog(s) & Work Here! WIFI & CABLE Beautiful Restful Retreat! Come experience award-winning wineries, antique shops, art galleries, Summer 2017 - Let me know your...
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    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southold
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Washer
    • Parking
    • Internet Access
    • Air Conditioning
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated with two new full bathrooms, new kitchen and second floor bedroom/family room with glorious views overlooking the Long Island Sound, the Shorecrest Beach House has never looked so good! The Shorecrest beach house is located on a grassy bluff overlooking the ocean and available for...
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    Southold, North Fork 11971
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beach House In Wine Country; Huge Sun Room1 / 16
    (2)Excellent
    Southold
    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 May 3, 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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    Location Information
    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Mattituck
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Waterfront
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    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house has completely been renovated with a brand new kitchen. It has amazing panoramic views and a large wrap around deck. Kitchen, bathroom and outdoor shower. This home is directly on the beach and located in the heart of the North Fork right by all the vineyards and farm stands! Comes with...
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    Mattituck, North Fork 11952
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Ocean Views
    • Washer
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    near beach 3 Bedrooms and 1.5 baths Plus and outdoor shower, nice yard,WiFi,bbq Begin Description: Awesome Beach House (less than 50 yards [30 second walk to the beach] from private sandy bay beach) location location location This House was built in the 1700's (revolutionary era) and has been...
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Patio
    • DVD Player
    • Grill
    • Housekeeping Included
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peaceful Year-Round Escape in the Middle of Wine Country It's starting to warm up so come to the North Fork - Sip local wine on the front porch or watch the waves at the private beach which is just a short walk away. Relax and kick back in our 3 bedroom house in Long Island's North Fork. Close...
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Southold
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Grill
    • Private Yard
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large beach front with 5 bedrooms (2 ensuite), 4 living rooms, 3.5 baths This is the perfect home for the extended family vacation, with not only 5 bedrooms, including 2 with ensuite bathrooms but 4 separate sitting/family/den or game rooms plus a pool room! The unique layout offers areas to gather...
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    Southold, North Fork 11971
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Southold
    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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    Location Information
    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southold
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Ocean Views
    • Porch
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to this idyllic beachfront located directly on the Sound in Southold NY, only 1 hour 45 minutes from NYC. Open-air, camp-style rooms are part of the house's simple charm. Linger over meals with family and friends on the screened-in porch, watch mesmerizing sunsets, swim in the salt water,...
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    Location Information
    Southold, North Fork 11971
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms 3 Bathroom home for rent. Beautiful landscape and privacy on a full acre with gigantic fenced in backyard with playground. 5 minute walk or 1 minute drive to private community Peconic Bay beach. Excellent condition and comfort. Weber Grill, sun filled deck , quality entertainment system....
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    North Fork Beach Cottage in  New Suffolk1 / 19
    (1)Excellent
    New Suffolk
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Yard
    • 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Yard
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Guests are sure to enjoy a memorable vacation in this Pristine 3 bedroom/2 bath contemporary property in a quiet bay front community located steps away from a private beach facing Shelter Island and across from a well known North Fork vineyard. This property is located on a quiet dead end street...
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    North Fork Beach House on LI Sound1 / 14
    (1)Excellent
    Peconic
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 27, 2018
    House had everything we needed to enjoy a vacation at the beach. Great outdoor barbecue area, huge outdoor shower. Sunsets are amazing from the deck!Comfortable beds and...
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    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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    New Suffolk
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    • Porch
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    • 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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mattituck
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Housekeeping Included
    • Central Heating
    • Terrace
    • Grill
    • Ocean Views
    • Balcony
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This modern renovated beach house sits on landscaping that feels like an estate. Right on the Mattituck Inlet that opens up to the Long Island Sound a few yards away, boats pass though all day - the view is magical, yet you feel completely private, hidden behind thoughtful landscaping. A large...
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    Mattituck, North Fork 11952
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Mattituck
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Washer
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Space The New York TImes Real Estate Section on Sunday, Feb. 9th, 2014, talked about the multi-million dollar homes being built in the Hamptons. The article said, 'The look of the homes is evolving: modern is making a comeback, but modern in the guise of barnlike. 'The modern barn is the...
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    Mattituck, North Fork 11952
    Condo/Apartment - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    Mattituck
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Central Heating
    • Terrace
    • Housekeeping Included
    • Grill
    • Washer
    • Patio
    • Balcony
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful summer home with private dock and close to famous Long Island vineyards. Few minutes away by boat/kayak from famous steak houses restaurant. This home has a magnificent view of Mattituck inlet. The house is furnished tastefully with top of the range stainless steel appliances and huge...
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    Location Information
    Mattituck, North Fork 11952
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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