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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Spacious Entertainer's Dream Home 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 in 2014 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 a few hours
Response rate:
Calendar last updated:
August 9, 2017


Southold House Accommodation and Amenities

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
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • 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
  • Satellite / Cable
  • Television
  • 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 -
(36 traveler reviews)

97% Complete
2% Complete
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Spacious Entertainer's Dream Home Close to Wineries/Beaches, Featured on HGTV
average rating of 4.9722223 based on 36 reviews

Convenience on the North Fork

  • 5 of 5

Great lay-out for a vacation home. Spacious, with a great kitchen as the focal point for downstairs. Large bedrooms with comfortable beds and linens / pillows. Plenty of bathrooms and showers. Private sitting room with its own HDTV off of the dining area. Large family room with HDTV. Nice entry foyer. Just a very nice house, well kept, comfortable furniture. We felt right at home immediately. Convenient to the wineries, to Greenport. Cutchogue, the Orient Point Ferry.

  • Submitted: May 30, 2017
  • Stayed: May 2017
  • Source: HomeAway
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  • 5 of 5

What a beautiful home to celebrate any occasion or just spend time together. The house is gorgeous and the layout makes it able to spend time together without being on top of each other. The main living space is open concept with plenty of room. The house is beautifully furnished with everything you need at your fingertips. Location couldn't be better for enjoying all that the North Fork has to offer. The owner accommodated our every request, offered helpful advice and answered all questions we had. I can easily see our family coming back year after year!

  • Submitted: Apr 24, 2017
  • Stayed: Apr 2017
  • Source: HomeAway
Owner's Response: Thanks so much Ruth! We would love to have your family come and stay again!
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Nice design and spacious home close to beach

  • 5 of 5

We met here for a family reunion and the house worked perfect for what we wanted. Jackie communicated with us very well and in a prompt manner. We were here during the off season so didn't use the private beach nearby but looks like it would be nice and was within walking distance. House was well designed with lots of room to spread out yet plenty of room for all of us in the entertaining areas of the kitchen and dining room. The beds were very comfortable and although the bathrooms wee dated they were immaculately clean. We all enjoyed our stay very much! Everything you'd expect from a cozy coastal home.

  • Submitted: Feb 19, 2017
  • Stayed: Feb 2017
  • Source: HomeAway
Owner's Response: Thanks Jen! I'm glad you enjoyed your stay and hope you will stay again.
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Long Island


  • 5 of 5

This was such a lovely and warm home. It was immaculate and so spacious. The bedrooms was large and extremely comfortable. The owner was amazing to work with, quick response time and answered every question. All directions was easy to follow. We were a group of five women on a girls weekend and had a great time. Do no hesitate to book this house!! Everything you need is there.

  • Submitted: Feb 2, 2017
  • Stayed: Jan 2017
  • Source: HomeAway
Owner's Response: Thank you Janice, hope you will stay again!
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The home was beautiful and Jackie was extremely organized, helpful and responsive.

  • 4 of 5

Jackie was a wonderful help from the start of this process and during our stay. The home was spacious, inviting and the rooms were comfortable. The binder with nearby eateries and recommendations for activities was really helpful as was the binder for the hot tub and home instructions. Overall, it was a great girls' weekend in a wonderful home!

  • Submitted: Dec 18, 2016
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
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Great house

  • 5 of 5

The house is very nicely laid out, great for a group. Jackie is a pleasure to work with. Everything we needed was in the house. Close to many nice restaurants. The house was clean and comfortable.

  • Submitted: Nov 23, 2016
  • Stayed: Nov 2016
  • Source: HomeAway
Owner's Response: Thanks Ginny! I hope your group decides to stay again!
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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

Southold House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
August/Labor Day
Aug 1 2017 - Sep 4 2017
14 night minimum stay
Early Harvest 2017
Sep 5 2017 - Oct 23 2017
2 night minimum stay
Late Harvest
Oct 24 2017 - Nov 19 2017
2 night minimum stay
Thanksgiving 2017
Nov 20 2017 - Nov 30 2017
3 night minimum stay
December 2017
Dec 1 2017 - Dec 21 2017
2 night minimum stay
Dec 22 2017 - Jan 2 2018
3 night minimum stay

Additional information about rental rates

Cleaning Fee $180
Damage Deposit $500

**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.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.

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