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Vacation Rentals near Sag Harbor Sailing

51 Pine Neck Ave, Sag Harbor, New York 11963-1702
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    Travelers to Sag Harbor are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 62 Rentals in Sag Harbor
    Chic and Modern Beach retreat with heated Pool1 / 16
    (1)Excellent
    0.4 miles from Sag Harbor Sailing
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Cottage in the historic district1 / 11
    (1)Excellent
    2.8 miles from Sag Harbor Sailing
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Elegant Designer Hamptons Retreat in Sag Harbor1 / 28
    (5)Excellent
    2.3 miles from Sag Harbor Sailing
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Sag Harbor designer home, Chef's kitchen & one block from the water1 / 14
    (2)Excellent
    0.9 miles from Sag Harbor Sailing
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Yard
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 12, 2017
    We loved everything about this place. From the outdoor fire pit to my elderly parents having the time of their lives. Everything was impeccable. We look forward to returning...
    Reviewed March 23, 2017
    Our family enjoyed a great week in Sag Harbor and wonderful accommodations. The house is as advertised, nicely and warmly decorated with beautiful pool and outdoor grounds. The...
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    About this property
    For a truly authentic experience of Sag Harbor, stay at this delightful 5-bedroom, 2-bathroom designer's home with oversized heated pool and ideally situated just 2 blocks from Long Beach . With 2,800-square feet of living space and enough sleeping accommodations for up to 10 guests, this residence...
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    Sag Harbor, Hamptons
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    2.0 miles from Sag Harbor Sailing
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Yard
    • Wi-Fi
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful custom built 2 bedroom home offers authentic charm and elegance from the finishing to the furnishings. It is located in a waterfront community just steps to the Peconic Bay with access to launching your boat! Enjoy the view of the heated pool from a spacious deck overlooking a large...
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    Sag Harbor, Hamptons
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.8 miles from Sag Harbor Sailing
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a newly renovated bungalow with 2 bedrooms, full living room, eat-in kitchen, closed in and sunny porch, roomie deck with outdoor furniture (in season). It is a 5-10 minute walk to the village, fine restaurants, museums, shops, churches and temple and beach.This is a prime location. The...
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    Sag Harbor, Hamptons
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1.9 miles from Sag Harbor Sailing
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
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    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy 2 acre beautiful parcel adjacent to hundreds of acres of town reserve sits this updated light filled home with sweeping lawn, and reserves on 3 sides for complete privacy. Spacious with 4 bedrooms and 3.5 baths,Two masters with king beds and private baths, two additional bedrooms one...
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    Sag Harbor, Hamptons
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Sag Harbor Village Fringe, Great Location1 / 18
    (1)Excellent
    3.7 miles from Sag Harbor Sailing
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 29, 2018
    Was very happy with house , I had a wedding in Sag harbor and close proximity to town was perfect. Lovely property just wish it was warm enough to use the pool....
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    About this property
    This property has just gone through a hi-end renovation. It has a beautiful updated Viking kitchen, amazing yard with a 50 ft gunite pool with shallow end 'tanning bed', great for kids and adults alike! There are four bedrooms, 3 full baths in the main house, plus an additional full bath in the...
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    Sag Harbor, Hamptons
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1.0 miles from Sag Harbor Sailing
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    OPEN HOUSE!! Sunday May 18 One of the last houses in the area with pool AND tennis! MD-LD $60,000 Please call first. Welcome to my paradise! My home has everything you need for a fantastic summer. 6 bedroom/4 bath contemporary home on 10 secluded acres. Heated in ground 20x40 pool, all weather...
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    Sag Harbor, Hamptons
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Beech Tree Cottage1 / 16
    (5)Excellent
    2.1 miles from Sag Harbor Sailing
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Shared Yard
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    • Outdoor Dining Area
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    • 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1.6 miles from Sag Harbor Sailing
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
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    • Grill
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy acre beautiful parcel sits this updated light filled home in a Development with wide street for walking. With 4 Master Ensuite bedrooms, spacious with 2 masters with king beds and private baths, one with queen bed and private baths and the other with two twin beds and private bath...
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    Sag Harbor, Hamptons
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    2.5 miles from Sag Harbor Sailing
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning, spacious three bedroom home, with water views from every room, and a heated gunite pool, will be your dream-come-true vacation rental. You will be minutes away from several gorgeous beaches as well as 1 mile from the lively and historic village of Sag Harbor. Decorated to a high...
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    Sag Harbor, Hamptons
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.6 miles from Sag Harbor Sailing
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Grill
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is nestled in a park like setting with a private tree-lined yard. You will have all the privacy you want. Enjoy a beautiful built in pool & jacuzzi. The home is clean, stylishly decorated, and steps away from a gorgeous North Sea bay beach. Visit Southampton or Sag Harbor town only 3 min...
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    Sag Harbor, Hamptons
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2.3 miles from Sag Harbor Sailing
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Wi-Fi
    • Patio
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect Summer rental! 3 bed, 2.5 bath Cape Cod style home with partially finished basement. Backyard oasis with pool, grill and fire pit. Meticulously maintained and lots of sunlight. Open concept kitchen, dining and living room. Master bedroom with king bed and ensuite on first floor with...
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    Sag Harbor, Hamptons
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3.6 miles from Sag Harbor Sailing
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Our beautiful Beach Song Cottage is located in the private beach community in the village of Sag Harbor. Bike or walk to the beach, take an afternoon stroll with a bottle of wine and enjoy the Perfect Sunset. The cottage is fully furnished, beautiful outdoor space to barbecue or have afternoon...
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    Sag Harbor, Hamptons
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.5 miles from Sag Harbor Sailing
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay at our Cozy Beach House located in the village of Sag Harbor. This beautifully renovated, three-bedroom, two-bathroom beach home. This 5-star home comes with 5-star services to match. When booking this home, you are granted access to the incomparable perks of Checkkin, your custom vacation...
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    Sag Harbor, Hamptons
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.1 miles from Sag Harbor Sailing
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Housekeeping Included
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abundance of natural light with 4...
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    Sag Harbor, Hamptons
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.9 miles from Sag Harbor Sailing
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Cable/satellite TV
    • Balcony
    • Grill
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your dream vacation awaits at this beautiful English manor on over an acre of private estate, just a two-minute walk from the beach overlooking the bay. Sag Harbor Luxury Estate is the ideal home for your next Hamptons holiday. Come and unwind by the 40-foot heated pool or take a trip to the town...
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    Sag Harbor, Hamptons
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    3.0 miles from Sag Harbor Sailing
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    • Grill
    • Patio
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The feeling of Zen surrounds you as you enter upon this European designer's hideaway..Custom appointments of quality and luxury fill this Hampton's home. Located 12 minutes walk to Main Street of the prestigious Sag Harbor Village....0.4 acres of beautifully manicured totally private lawns with...
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    Sag Harbor, Hamptons
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3.2 miles from Sag Harbor Sailing
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Our house is light filled and open. We are a 15 min. walk to town and a 10 min walk to the bay. The neighborhood is quiet yet close to all. We are also a short distance (5 min walk) to the Harbor Market where they have really great coffee and yummy healthy food to eat in or take out. We use...
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    Sag Harbor, Hamptons
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.7 miles from Sag Harbor Sailing
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is one of the most sought after spots in Sag Harbor Village. It's a traditional cedar shingle house on gorgeous waterfront property (with an 80-foot private dock) and couldn't be situated in a better location. The majority of things you would need or would want to do in the area are within a...
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    Sag Harbor, Hamptons
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    0.8 miles from Sag Harbor Sailing
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • Hot Tub
    • Ocean Views
    • Balcony
    • Grill
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, This is a wonderful beach house to stay over the summer. It has everything you want in it (Salt Water Pool, Wreck Room, Jacuzzi, Home Theater, Alarm Systems, etc...)! For those who want the best, come here. It has wonderful views of beaches. In under 100 yards, you can be at the best...
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    Sag Harbor, Hamptons
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2.7 miles from Sag Harbor Sailing
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    Village traditional on a quiet village street perfect for family gatherings. Magnificent backyard including a stone patio with fridge, grill, heated gunite pool and beautiful gardens. The park is accessible from our backyard allowing children to enjoy fields and playground and adults to have...
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    Sag Harbor, Hamptons
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Chic Bridehampton Pristine Designer Home + Free Pool Heating!1 / 20
    (8)Excellent
    3.6 miles from Sag Harbor Sailing
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 13, 2018
    We had a wonderful time at "the white house." It was light, bright, lovely, cheerful, clean and a perfect layout for the five of us - we were able to sleep in and enjoy...
    Reviewed March 14, 2018
    This house is amazing! We celebrated a girls weekend with 6 people, and it was perfect for us — so spacious, clean, bright and beautiful. Every guest was blown away by the house...
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    About this property
    Bridgehampton White House RATES INCLUDE THE FOLLOWING: Electric consumption, cable TV & wi-fi, propane consumption, telephone, trash removal, lawn & pool service and pool heater set to 85 degrees between Memorial Day and Labor Day** OVERVIEW OF HOME: 3 bedrooms 3 bathrooms Finished Basement with...
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    Bridgehampton, Hamptons
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beach House In Wine Country; walk to beach, large sun room, outdoor dining1 / 16
    (2)Excellent
    4.4 miles from Sag Harbor Sailing
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Air Conditioning
    • Porch
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    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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    Southold, North Fork
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Spacious Home with Pool in Heart of the Hamptons!1 / 33
    (2)Excellent
    3.1 miles from Sag Harbor Sailing
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Grill
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 19, 2016
    All I can say is WOW! Patrick's home is a dream!! Patrick has done an amazing job decorating this home. It was so comfortable inside and out from tasteful furnishings, a...
    Reviewed July 18, 2016
    This has it all, in a Perfect location, convenient to Hamptons shopping, beaches, restaurants, with the quiet of a private retreat. The house has large open rooms for...
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    About this property
    This beautiful home is in a great location, was just renovated and is luxuriously furnished and thoughtfully appointed (including original art, and luxury linens, kitchenware and dishes new for 2016). Perfect for relaxation and entertaining, highlights include: -Large open concept family room...
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    Water Mill, Hamptons
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2.5 miles from Sag Harbor Sailing
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely home on prime BH North Street, with privacy and lots to do around. Gourmet kitchen with good knives and all clad. Garden is organic with lots of herbs and flowers. There are 3 whirlpool baths. One king. Size bed is sleep number. Owners want you to enjoy!
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    Bridgehampton, Hamptons
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Bridgehampton Village Beauty1 / 26
    (1)Excellent
    4.9 miles from Sag Harbor Sailing
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2018
    Beautifully decorated and spacious house. The perfect summer getaway! Everything from the pool, to the fireplace outside, and everything else made my stay enjoyable and super...
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    About this property
    Our home is a beautiful and serene oasis in the heart of Bridgehampton Village. A gourmet kitchen, three dining areas, an indoor and outdoor fireplace, four separate sitting and relaxation areas, a pool house with a bar and large screen tv. The house is a place where multiple generations can...
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    Bridgehampton, Hamptons
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4.2 miles from Sag Harbor Sailing
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4.5 miles from Sag Harbor Sailing
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated with top of the line furniture, this house is close to: world renown Sunset Beach restaurant by famed owner Andre Balazs, Commander Cody's, Marie Eiffel Dockside Market, Mashomack Preserve, Salt Restaurant, Sylvestor Manor, Gardeners Bay country club, Shelter Island Heights, and the...
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    Shelter Island Heights, Shelter Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.6 miles from Sag Harbor Sailing
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    • Patio
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well appointed 7000 sq. ft. traditional Hamptons home situated on 1.40 acres bordering a 32 acre reserve. 6 bedrooms and 5.5 baths, huge eat in kitchen, formal living and dining rooms, bar and an oversized gunite salt water pool and spa. Center foyer opens to a dining room with butler's pantry,...
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    Water Mill, Hamptons
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3.7 miles from Sag Harbor Sailing
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Patio
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    • Private Outdoor Pool (Heated)
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful contemporary home set on 1.6 private idyllic acres. Walk to town, near beaches. Easy drive to Sag Harbor, Southampton and East Hampton. Right by Hampton Classic and Polo grounds. New designer furnishings and linens. Separate master suite with Jacuzzi and steam shower. 3 Additional...
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    Bridgehampton, Hamptons
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Romantic Getaway in Southampton (private room/bathroom)1 / 14
    (1)Excellent
    2.8 miles from Sag Harbor Sailing
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 21, 2018
    Great location. Beautiful grounds. Gracious host. The home was easy to find, peaceful and located in an area of that made getting around central Long Island simple and...
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    About this property
    Newly renovated house with nice spacious rooms with comfortable new double beds. Double occupancy room /private bathroom/entrance, queen size bed newly renovated 4 bedroom-3 bathroom home in prime Southampton location. Close to bay, beach and town. Directly across the street from the fascinating...
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    Southampton, Hamptons
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Very Private and Tranquil  House in wooded estate.1 / 20
    (6)Excellent
    2.8 miles from Sag Harbor Sailing
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 25, 2017
    Let me share my impression in short: very convenient location, exceptional cleanliness in rooms, outdoor pool, beautiful plot, very friendly host Lydia. There is not better...
    Reviewed August 15, 2017
    Wonderful casa tua! Very welcoming , beautiful house , gracious hosts , great breakfast and beautiful backyard and pool.Highly recommend!
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    About this property
    This well-appointed and maintained 2,200 sq.ft., 4 bedroom, 3 bath Contemporary has a bright sunlit breakfast area directly off the gourmet kitchen, Situated on a sprawling manicured acre with a 20x40 sparkling swimming pool and directly across the street from the fascinating Peconic Bay with...
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    Location Information
    Southampton, Hamptons
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3.8 miles from Sag Harbor Sailing
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely 4 bedroom home backs to preserve and is located just north of the village with an open floor plan and wonderful light and high ceilings throughout. Main floor has guest bedroom and bath, living room with fireplace and double height ceilings, separate dining area and eat-in kitchen, which...
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    Location Information
    Bridgehampton, Hamptons
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3.3 miles from Sag Harbor Sailing
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of the Hamptons- Pet friendly 4 Bedrooms, 4 Bathrooms, Sleeps 8 This cozy getaway is located off of Deerfield Road in Southampton and provides easy access to the towns of Southampton, Sag Harbor, Bridgehampton and Water Mill. It is just a short drive to restaurants, shopping,...
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    Location Information
    Water Mill, Hamptons
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3.5 miles from Sag Harbor Sailing
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy furnished country-style farmhouse sleeps ten people comfortably and is minutes to ocean or bay beaches, shopping, and restaurants. The house sits on over an acre of land adjacent to 1,000-acre Long Pond Reserve. Out back is a wooden deck, an in-ground pool, and a pool house. There are 8...
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    Bridgehampton, Hamptons
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3.6 miles from Sag Harbor Sailing
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    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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    Location Information
    Southold, North Fork
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.4 miles from Sag Harbor Sailing
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    • 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    4.3 miles from Sag Harbor Sailing
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Housekeeping Included
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the front is a beautiful woodland garden with rare woodland flowers and ferns, moss-covered boulders and miniature ponds. In the rear is a Japanese garden, complete with a moon bridge over a babbling brook, a waterfall you can swim behind, a pond house with a deck you can sunbathe or dive from,...
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    Southampton, Hamptons
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3.9 miles from Sag Harbor Sailing
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Yard
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southampton, Luxury 4 Bed 2 Bath home with pool, minutes to everything! New 25 x 50 Salt Generated Pool, no maintenance and much easier on the eyes! 3 Minutes to Private Beach! Free Parking, NO Beach Passes needed! This 4 bedroom, 2 bath home is nestled on 1.5 acres which abuts a 10 acre...
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    Southampton, Hamptons
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bridgehampton South, Village Gem.  Location, Location, Location!1 / 16
    (4)Excellent
    4.8 miles from Sag Harbor Sailing
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 6, 2018
    The house is really idyllic. It's close enough to everything so you can easily feel part of the action but secluded enough on a tucked away road that you can cocoon yourselves...
    Reviewed March 5, 2018
    Susan’s Bridgehampton home was the absolutely perfect getaway spot for my fiancé and me. This home is a gem. The perfect charmer that’s hard to find among all the ubiquitous...
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    About this property
    Location, location, location!! Centrally-located, south of the highway charmer with easy layout and great vibe. Sun drenched, post modern with vaulted ceilings, oversize windows and exposed beams running throughout house. Expansive great room and open floor plan is fantastic for entertaining,...
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    Location Information
    Bridgehampton, Hamptons
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.0 miles from Sag Harbor Sailing
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Cable/satellite TV
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    • Balcony
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    • 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4.7 miles from Sag Harbor Sailing
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3500 sq ft Hampton's styled home has a large light filled living room with fireplace and sliding glass doors to the expansive deck with heated pool. The open floor plan makes this home perfect for entertaining. This home is situated on .75 of an acre of property that backs up to a private...
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    Location Information
    Water Mill, Hamptons
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    3.1 miles from Sag Harbor Sailing
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely Hamptons Cottage. 2BR with w/d on site and plenty of off street parking. Lovely ponds and peaceful environment. Central to accessing all of the Hamptons. Internet, Cable TV, Wifi, contemporary design. New furniture. Full kitchen. Outdoor patio. Lovely landscaping. Nature walks. Enjoy a...
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    Bridgehampton, Hamptons
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3.0 miles from Sag Harbor Sailing
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Grill
    • DVD Player
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    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique, romantic beach cottage on the water 11 steps from actual water. Mini waves crash, ocean breezes, amazing water and sunrise views. Windows galore. Experience one of the most memorable getaways you will never forget. Cozy, romantic immaculate new beach cottage, just finished and slept in...
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    Noyack, Hamptons
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4.9 miles from Sag Harbor Sailing
    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Parking
    • Balcony
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the exclusive Wainscott hamlet of East Hampton and situated between East Hampton Village with its world renowned shopping and beaches, and the historic village of Sag Harbor; this 6 bedroom, 3.5 bath post-modern home comfortably sleeps 10 and is ideally located on a private cul-de-sac...
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    Location Information
    East Hampton, Hamptons
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 11
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    3.7 miles from Sag Harbor Sailing
    7 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Sauna
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful estate home in Water Mill, New York borders the prestigious Matt Lauer's 40 acre horse farm with distant ocean views. This estate features 7 bedrooms with 7 en suite bathrooms, 2 1/2 baths, two master bedrooms. There are five full masonry fireplaces, pool room, wine room, cigar...
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    Location Information
    Water Mill, Hamptons
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 10
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    3.9 miles from Sag Harbor Sailing
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful sundenched hamptons property recently renovated quiet and private yet centrally located to all ocean and bay beaches, shopping and transportation. Bike to beaches, towns of Bridgehampton and Sag Harbor. Vineyards and farm stands just up the street. Dead end street location great for kids...
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    Location Information
    Bridgehampton, Hamptons
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3.2 miles from Sag Harbor Sailing
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Private Yard
    • Secure Parking
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Guests are sure to enjoy a memorable vacation in this fully furnished, 6 bedroom/ 7 bath home in a private, gated, park like setting. The 3 master bedrooms have 2 bedrooms with a king-sized bed, 1 with a queen size bed while the remaining rooms are furnished with a full-sized bed (2) and bunk...
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    Location Information
    Southampton, Hamptons
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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