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Spacious Family Retreat Close to Wineries/Beaches, Featured on HGTV

Bedrooms 4
Space 3,000 sq ft
Property type house
Minimum Stay 2 - 14 nights


About the property

4 Bedroom, 3 Bathroom home on private lot in private beach association community

This home was renovated on the HGTV show 'Vacation House for Free'.

This newly renovated home, with it's coastal vibe, is perfect for a weekend getaway or summer long retreat. Located in a private beach association community, it boasts a brand new kitchen and open floor plan. The beautiful kitchen with it's oversized island opens up into a large dining and living area. The kitchen has brand new quartz countertops and stainless steel appliances, including a wine fridge. Gather around the kitchen island, which can seat up to 6, while dinner is being prepared. Enjoy your meal at the dining room table which can seat up to 8.

The sizable living room has a large flat screen tv with plenty of seating to gather round. In addition, there is a bright sunroom off the dining/living room that can be a quiet retreat to read a good book or watch a movie.

There are 4 ample-sized bedrooms, all with generous double closets, and 3 full baths. There are 2 bedrooms upstairs and 2 bedrooms downstairs, which makes this home perfect for 2 families to share. The first bedroom downstairs has a queen size bed and the other has a king size bed. The upstairs bedrooms are extra large and very spacious. The first upstairs bedroom has a king size bed and the second has four twin beds. Between to the two upstairs bedroom is a study area perfect for your laptop (Wifi throughout).

Off the kitchen and leading to the back deck, is a beautiful and airy tasting room, with a custom built reclaimed wood bar and wine barrel bistro table. From the tasting room, pass through one of the two sliding glass doors to the private backyard which features a hot tub (fits 6), Weber gas grill, and a large dining table that can seat 10 people.

The private beach association beach is a 3 minute walk from the house. Spend the day there to enjoy the cool breeze and watch the boats or head there after a day at the wineries, farms, and shops, to watch the beautiful sunset.

Lastly, the home has a large 2 car attached garage making it easy to bring in groceries and bags and to keep your car covered.

More Details

Jacqueline OConnor
Member since: 2014
Speaks english
Response time:
Within an hour
Response rate:
Calendar last updated:
June 20, 2018


Accommodation and Amenities for this vacation house rental in Southold, New York

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 3000 sq ft
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 12:00 PM
  • Max. occupancy: 10
  • Min. age of primary renter: 30
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • No more than 4 cars at the property at a time.
  • Away From It All
  • Family
  • Romantic
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace
  • Garage
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Child's Highchair
  • Dining
  • Dining Area
  • seating for 8 people
  • 3 Bathrooms
  • Bathroom 1 - toilet , combination tub/shower , shower , bidet
    Bathroom 2 - toilet , shower
    Bathroom 3 - toilet , shower
  • 4 Bedrooms, Sleeps 10
  • Bedroom 1 - 1 queen
    Bedroom 2 - 1 king
    Bedroom 3 - 1 king
    Bedroom 4 - 4 twin/ single
  • DVD Player
  • Ping Pong Table
  • Television ...
  • Toys ...
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • long term renters welcome
Pool / Spa:
  • Hot Tub
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • marina
  • museums
  • playground
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • boating
  • miniature golf
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • hunting
  • ice skating
  • jet skiing
  • kayaking
  • pier fishing
  • sailing
  • sound/bay fishing
  • swimming
  • water tubing
  • wind-surfing


Exceptional! 5/5 -
(45 traveler reviews)

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4% Complete
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Spacious Family Retreat Close to Wineries/Beaches, Featured on HGTV
average rating of 4.9555554 based on 45 reviews

Wonderful stay close to everything

  • 5 of 5

The house was super clean, beds were comfortable and had more than everything we could hope for. Jackie was a huge help with our millions of questions and very prompt in her responses. We couldn’t have asked for a better stay! We will definitely be back and recommend to friends.

  • Submitted: 4-Jun-2018
  • Stayed: May 2018
  • Source: HomeAway
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Amazing Family Vacation Home

  • 5 of 5

Jackie was so wonderful to work with and her home is just the perfect family vacation home! We stayed with my family for my wedding weekend and it was just wonderful to be able to have everyone under one roof! Her home is spacious and absolutely beautiful! The outdoor seating and hot tub were real fan favorites and the kitchen is spectacular! Highly recommend staying at Jackie’s home, I know we will be back again!

  • Submitted: 2-Jun-2018
  • Stayed: May 2018
  • Source: VRBO, from HomeAway
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Picture perfect!

  • 5 of 5

This property is everything the listing promises and more. I stayed here to celebrate my friends 40th birthday. There was plenty of room for all 10 of us. We cooked dinner together for each of the 2 nights we stayed and the kitchen was perfect for chatting, snacking and cooking. The finishes were superb and felt like we were staying in a luxury resort. The location is perfect for some day trips to the local wineries. Greenport Harbor Brewing is perfect for a quick lunch and a brew. I would highly recommend this house and would love to spend my 40th birthday there as well!

  • Submitted: 31-May-2018
  • Stayed: May 2018
  • Source: HomeAway
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  • 5 of 5

Wonderful stay for a family weekend! The owner is very accommodating and the house is beautiful. The kitchen/living area is perfect for entertaining. Would highly recommend!

  • Submitted: 23-Apr-2018
  • Stayed: April 2018
  • Source: HomeAway
Owner's Response: Thanks so much! I hope you will stay with us again!
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Beautiful updated rental! Everything we needed!

  • 5 of 5

Beautiful house. Sparkling clean. We are a group of 10 ladies celebrating together. Large space was perfect for gathering. Wine fridge was perfect touch. Kitchen had everything we needed. Cleanest and nicest hot tub I've ever experienced in a rental. Nice short walk to the beach. Location central to everything but far enough from main road so that it was peaceful & quiet. Hostess communication was quick & thorough. We really appreciate her hospitality!

  • Submitted: 15-Apr-2018
  • Stayed: April 2018
  • Source: HomeAway
Owner's Response: Thanks so much Kathleen! I hope you will stay again!!
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Very nice, CLEAN, well equipped house

  • 4 of 5

My friends and I love to rent a nice house for our “Girls Weekends” a few times a year! We have rented on Long Island, Connecticut and do not always get a place that has everything you might need, is immaculately clean AND has a perfect set up. You DO however, get that in this house!!

Also very important is how responsive the owner is and Jackie replies promptly to emails. Overall, I would recommend this house without reservation.

  • Submitted: 14-Jan-2018
  • Stayed: January 2018
  • Source: VRBO, from HomeAway
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Nearest Ferry
16.7 Miles
Cross Sound Ferry
Nearest Train
3.4 Miles
Southold LIRR
Nearest Beach
0.2 Miles
Bay Haven Association Beach
Car: necessary

Centrally located in the North Fork, this house is close to wineries, farms, shopping, restaurants, beaches, and marinas.


Rates & Availability

Rental Rates for this vacation house rental in Southold, New York

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
June 2018
May 29 2018 - Jun 30 2018
3 night minimum stay
July 2018
Jul 1 2018 - Jul 30 2018
7 night minimum stay
August 2018 - Labor Day
Aug 1 2018 - Sep 3 2018
14 night minimum stay
Early Harvest 2018
Sep 4 2018 - Oct 28 2018
2 night minimum stay
Late Harvest 2018
Oct 29 2018 - Nov 20 2018
2 night minimum stay

Additional information about rental rates

Refundable Damage Deposit C$664.2
Cleaning C$239.11

**Newly enacted town law requires that all short term rental contracts be for a minimum of 14 nights. Please contact owner to discuss**

Cancellation Policy - 100% refund if canceled at least 30 days before arrival date.

Memorial Day 2018-Labor Day 2018 = $32,500

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.
Contact Owner