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Book Online or call HomeAway Booking Assistance +44-800-085-3815

Charming 1720 Historic Home, Easy Summer Living For Friends And Family.

Bedrooms 4
Separate WC's1
Property type house
Minimum Stay 2 - 5 nights
Popular Features
  • Internet
  • Washing Machine
  • Parking
  • Barbecue


About the property

4 Bedrooms, 2 Bathrooms, Sleeps 7

The Orient House is accepting reservations for summer 2017!

The Orient house makes for a classic eastern Long Island casual summer vacation: outdoor porches, fishing, bike to the beach, barbecues, local wine, fresh produce from the farm stand down the street, long days outdoors, warm nights, sky full of stars.

Its a great family house, children are welcome, the yard is fully fenced. We welcome your well-behaved pet.

Deborah Winsor
Member since: 2015
Speaks English
Response time:
Within a day
Response rate:
Calendar last updated:
15 May, 2017

About Deborah Winsor

I am a grade school educator and woodworker, previously having worked at residential and wooden boat restoration. The Orient house has been an ongoing labor of love and been host to many friends and families over the years. I'm sure you'll enjoy it as much as we do.

Deborah Winsor purchased this house in 1991

Why Deborah Winsor chose North Fork

The Orient house has been a home and vacation place for our friends and family for decades. Orient is a gracious peaceful area, rich in history, quiet and relaxed,

The house was built in 1720, it's a charming historic home with a comfortable family feel: exposed oak beams, hand-numbered mortises and old wood floors and doors that speak of the craftsmen who built the house.


Accommodation and facilities for this holiday house on the Orient on the Southold Town

Property Type:
  • house
  • Self-catering
  • Housekeeper Included
House Rules:
  • Max. occupancy: 7
  • non smoking only
  • pets considered ...
  • children welcome
Location Type:
  • near the sea ...
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Clothes Dryer
  • Heating
  • Internet
  • Linens Provided ...
  • Living Room
  • Parking ...
  • Towels Provided ...
  • Washing Machine
  • Wood Stove ...
  • Coffee Maker ...
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Oven
  • Refrigerator
  • Hob
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 1 Bathroom
  • 1 Separate WC
  • upstairs bathroom - Toilet , Bath with Shower
    downstairs bathroom - Toilet , Outdoor Shower
  • 4 Bedrooms, Sleeps 7
  • upstairs white room - 1 Large Double Bed
    upstairs child room - 1 Single Bed , suitable for child
    downstairs bedroom - 1 Large Double Bed
    upstairs blue room - 1 Double Bed
  • Games ...
  • Satellite / Cable
  • Television
  • Bicycles ...
  • Terrace
  • Garden
  • Barbecue
  • limited accessibility ...
  • churches
  • festivals
  • marina
  • museums
  • playground
  • restaurants
  • winery tours
Leisure Activities:
  • antique hunting
  • beachcombing
  • bird watching
  • Boating
  • Miniature golf
  • outlet shopping
  • photography
  • scenic drives
  • Shopping
  • sight seeing
  • walking
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • hiking
  • jet skiing
  • Kayaking
  • sailing
  • bay fishing
  • swimming
  • wind-surfing


Wonderful! 4.8/5 -
(6 traveller reviews)

Charming 1720 Historic Home, Easy Summer Living For Friends And Family.
average rating of 4.8333335 based on 6 reviews

Perfect Summer Vacation House

  • 5 of 5

My family and I had a glorious vacation in Deb's house. The house is charmingly rustic and clean and well equipped with plenty of room for all and a huge backyard. We biked to many different beaches each day and feasted on the local produce, seafood and wine. The kitchen had everything a cook would want and both a gas and charcoal grill are provided. Dinners on the back porch were festive and we'll think of them as the weather turns cold. Deb is a warm, welcoming and attentive host. We all hope to return next summer.

  • Review Submitted: Sep 24, 2016
  • Date of Stay: Aug 2016
  • Source: HomeAway
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1 0

Beautiful, relaxing, and easy to use

  • 5 of 5

We had a wonderful time in Deborah's house. It was close to everything, it was comfortable and beautiful, and Deborah was easy to reach and very friendly. Thank you, Deborah!

  • Review Submitted: Aug 18, 2016
  • Date of Stay: Aug 2016
  • Source: VRBO, from HomeAway
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0 0
New York

The house is a true gem as is the property. It was clean and comfortable and had what we needed

  • 5 of 5

Deb was there to greet us on arrival. She was very accommodating and gracious host. All our needs were met. Fresh sheets clean towels beach chairs outdoor grill washer/dryer beautiful outdoor shower the list goes on and on.

We were two couples each with one infant child in the house, which was very safe and comfortable. To note, for parents, there a staircase and the master bedroom on the ground floor has a ladder. Otherwise, totally safe and wonderful.

We would love to stay here again in the future. The North Fork is a wonderful.

  • Review Submitted: Aug 2, 2016
  • Date of Stay: Jul 2016
  • Source: VRBO, from HomeAway
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0 0
Sunnyside, NY

History in a House

  • 4 of 5

What a great historic home, almost 300 years old. They have done an good job of adding some modern touches into it. Well situated right on Main Rd. in Orient, although traffic and the noise may be an issue in really busy months. Easy walks or bike rides to both the north beaches and the southern bay/marsh areas. There is a gas station/deli right across the street so a quick morning coffee and egg sandwich is right there if you don't feel like making your own.

Fenced in yard all the way around is great for pets and gives them lots of room to run around and you don't have to worry about them getting loose.

Only issue was the outdoor shower didn't work, not sure if it was broken or the water to it was shut off, so there was no way to take a stand up shower during our stay, had to make do in the upstairs bathtub. Also, winter stays would also mean no stand up shower.

  • Review Submitted: Sep 27, 2015
  • Date of Stay: Sep 2015
  • Source: VRBO, from HomeAway
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0 0

Cool and cozy, great location!

  • 5 of 5

We had another property cancel on us at almost the last minute, but luckily, this house became available at almost the same time. It is comfortable, cozy and super convenient to Greenport and the local farms, beaches and parks. It definitely has the charm of a nearly 300-year-old house, but is well-equipped with everything you'd need from the 21st century (plus toddler toys, which our 3 year-old loved). One helpful note: we've been in other properties from the early 18th century that tend to have low ceilings, this is NOT a concern here - nice, high ceilings with exposed beams. Also the owner was extremely flexible and helpful, and even went down to the town clerk before we arrived to get us our beach parking permit in advance. Our favorite spot ended up being the little "Potato Beach" just down the road -- a calm, quiet, bayside beach perfect for swimming and splashing on a hot day. All in all, a great place to stay and enjoy a relaxing weekend on North Fork with the kids!

  • Review Submitted: Sep 1, 2015
  • Date of Stay: Aug 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you. I'm glad the house worked out for your family, and that you were able to take in so many of the great things the area has to offer! And, thanks for being such considerate guests. Enjoy the rest of the summer, a gorgeous autumn is on it's way!
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1 0
Philadelphia, Pennsylvania, USA

Cozy, comfortable, charming and close to everything we needed on the North Fork

  • 5 of 5

This house has a very warm and special feeling and was perfect for our stay in Orient. It is very comfortable and cozy, lovingly restored, combining charm with modern function. It has all of the modern amenities while maintaining its historic character. We especially loved the outdoor shower, creatively crafted of old wooden shutters! We grilled outside and enjoyed most of our meals out on the deck under the grape arbor. It was great have access to the bikes the owners provided for the five minute ride to the beach, explore the town and surrounding areas, and look up at the stars from the back deck at night. Everything we needed was nearby: The fish market in Southold is a short drive away and boasts an array of the freshest local and imported fish and shellfish. The North Fork is a winery destination and we enjoyed trying the local wines and pairing them with the fish and produce from the many farm stands. And The Orient Country Store carries delicious home-baked treats and last minute necessities. We felt completely at home in this lovely house, we so very much enjoyed our time there, and were sad to leave. We plan to return with family and friends to once again enjoy all that the house, Orient and the North Fork of Long Island have to offer.

  • Review Submitted: May 14, 2015
  • Date of Stay: May 2015
  • Source: VRBO, from HomeAway
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6 0


Nearest Airport
60 Miles
All NYC 2 hours, Macarthur (LI) 1 hr
Nearest Barpub
6 Miles
Greenport, several
Nearest Ferry
3 Miles
Orient Point, NY
Nearest Golf
3 Miles
Islands End Golf and Country Club
Nearest Train
6 Miles
Greenport, NY (LIRR)
Nearest Restaurant
6 Miles
Greenport, several
Nearest Beach
0.5 Miles
Car: recommended

Orient and the North Fork is renowned for it's vineyards, local fish markets and outstanding farm stands. The house at Platt Road is a base for an awesome cooking or dining out vacation. There are several lovely beaches within sort bike ride or driving, great for families or quiet sitting. For birders or walkers Orient and the North Fork offer miles of varied trails, and of course the water is just down the street for sea and bay kayaking, swimming, and small boat sailing.

Greenport, Shelter Island and the North Fork towns offer wonderful shopping, libraries, and activities for children. Riverhead, 30 minutes west has a great Tanger Outlet and several shopping malls, Six Flags Water Park, miniature golf, and Riverhead Motor Speedway for a fun change of pace.


Prices & Availability

Prices for this holiday house on the Orient, Long Island

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
Summer 2017
27 Apr 2017 - 30 Oct 2017
2 night minimum stay
for 2 nights
My Standard Rate
5 night minimum stay
for 5 nights

Additional pricing information

Pet Fee £77.3
Property Damage Protection £61.07
Tax Rate 4.0%

Owner's Cancellation Policy

  • 50% refund for cancellations more than 30 days before check-in date.
  • 100% refund for cancellations more than 60 days before check-in date.
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