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Secluded Getaway W/pool in the Heart of Long Island's Wine Region & Near Beach!

Star Rating



5.0 / 5Exceptional
2 reviews


  • Pool
  • Kitchen
  • Air Conditioning
  • Pet Friendly


What's nearby

  • Popular Location
    Raphael Winery
    9 min drive
  • Popular Location
    Pindar Vineyards
    10 min drive
  • Popular Location
    Sylvester Manor
    35 min drive
  • Airport
    New Haven, CT (HVN-Tweed - New Haven Regional)
    196 min drive

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    About this area


    This vacation home is located in Southold. Horton Point Park and Goldsmith's Inlet Park reflect the area's natural beauty and area attractions include Shelter Island Tennis Club and Harbes Family Farm.

    What's nearby

    • Popular Location
      Raphael Winery - 9 min drive
    • Popular Location
      Pindar Vineyards - 10 min drive
    • Popular Location
      Sylvester Manor - 35 min drive
    • Popular Location
      Havens House - 37 min drive
    • Popular Location
      Mashomack Preserve - 39 min drive

    Getting around

    • Southold Station - 7 min drive
    • Westhampton, NY (FOK-Francis S. Gabreski) - 38 min drive

    About this property

    Secluded Getaway W/pool in the Heart of Long Island's Wine Region & Near Beach!

    This beautiful home is located in the Harbor lights community in Southold on a serene half acre that has a nature preserve behind the backyard allowing you to really unwind from city life no matter the time of year. Walk out the back of the house onto the deck and see the 16 x 32' pool, a fire pit, lounge chairs, and a gas and charcoal BBQ. When your on the large deck relaxing, I promise you will see more deer and wildlife than people and houses. There is truly no better place to get away from it all while still being in the heart of the North Fork wine country, restaurants, and nightlife. You can walk to the private deeded beach where you can leave your kayak, light up one of the provided barbecues or just lay in the sand if you choose. This beach is only open to residents of the Harbor Lights Community and really feels like a small town beach when you go. Being on the North Fork also means that you have easy access to the various Southold Town beaches as well. The spacious house is recently renovated inside and out as well as tastefully decorated. It is a fully furnished 4 bedroom, 4 bathroom home with a finished basement, and a massive open floor plan on the main floor which makes it perfect for entertaining or spending quality time with the family. A large handmade dining room table seats 8 - 10 comfortably and so does the custom picnic table outside if you want some vitamin D. The backyard has a pool with a deck all around with several lounge chairs; right down the stairs is beach pebble hang out with a firepit & BBQ. The house is as perfect for large groups looking for a shorter trip to do some vineyard hopping and North Fork exploring as it is for a couple looking to get out of the city for an extended getaway that is close to home and everything in between. Ask us about our special for bachelorette parties and weddings!

    Property manager

    property manager


    Speaks English, Spanish, Greek



    Check-in time starts at 4:00 PM

    Special check-in instructions

    Guests will receive an email from the property manager with check-in and check-out instructions.


    Check-out before 11:00 AM

    Children and extra beds

    • Children are welcome.


    • Pets allowed
    • Restrictions apply
    • For more information contact the property at the number on the booking confirmation

    Payment types

    Important information

    You need to know

    Extra-person charges may apply and vary depending on property policy.
    Government-issued photo identification and a credit card, debit card, or cash deposit are required at check-in for incidental charges.
    Special requests are subject to availability upon check-in and may incur additional charges. Special requests cannot be guaranteed.
      Parties and events are allowed on site. 

    We should mention

    Guests can arrange to bring pets by contacting the property directly, using the contact information on the booking confirmation. A car is recommended for transportation to and from this property.

    Property is also known as

    • Remodeled Summer Escape House
    • Remodeled Summer Escape

    Property amenities


    • Private pool


    • Internet access

    Parking and transportation

    • Onsite parking


    • Refrigerator
    • Stovetop
    • Microwave
    • Oven
    • Dishwasher
    • Cookware/dishes/utensils
    • Toaster
    • Coffee/tea maker


    • 4 bedrooms
    • Bed sheets provided


    • 4 bathrooms
    • Shower/tub combination
    • Towels provided

    Living spaces

    • Fireplace
    • Living room
    • Dining room


    • TV with cable/satellite service
    • Pool or billiards table
    • Stereo

    Outdoor areas

    • Patio


    • Washing machine and dryer


    • Air conditioning
    • Heating


    • Smoke-free property

    Things to do

    • Water skiing nearby


    • Sleeps 14
    • Unit size: 2301 sq ft (214 sq m)

    Nearby things to do


    The recreational activities listed below are available either on site or nearby; fees may apply.
    • Water skiing nearby


    5 - Excellent
    4 - Good
    3 - Okay
    2 - Mediocre
    1 - Poor

    5/5 Excellent

    A wonderful stay in Southold.

    Theo's home is wonderful for a vacation spot. Not only is the property centrally located to the shops and town it is also a short walk to the bay. A quick ride away from Greenport this location is everything. It is in a quiet neighborhood and the house is beautiful and spacious to relax with your family. I would recommend this house to anyone who is looking for a getaway. An added bonus is that Theo allows dogs which is perfect for the dog-friendly North Fork.

    5/5 Excellent

    Nice place and very relaxing!

    Very comfortable house in the north fork area. Spacious with a great back yard with a nice bbq. In the morning we had deer strolling around. Unfortunately the pool wasn’t open, because of the temperature. A great home base from where you can go to the hamptons, New York and a lot of great parks and beaches. Theo had a lot of nice suggestions and was a great host!

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