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Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992
Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

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

Bedrooms 4
Separate WC's1
Property type house
Minimum Stay 5 nights


About the property

4 Bedrooms, 1-1/2 Bathrooms, indoor & outdoor shower, sleeps 6

The Orient House is accepting reservations for summer 2018!

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:
14 March, 2018

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 Orient

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 Town of Southold Town

Property Type:
  • house
  • Self-catering
  • Housekeeper Included
House Rules:
  • Check-in: 14:00 / Check-out: 11:00
  • Max. occupancy: 7
  • pets considered ...
  • children welcome
  • non smoking only
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 -
(11 traveller reviews)

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Charming 1720 Historic Home, Easy Summer Living For Friends And Family.
average rating of 4.818182 based on 11 reviews

Lovely rustic farmhouse

  • 5 of 5

Real farm house experience in Orient. Owner has created a wonderful seamless environment. Will be back.

  • Review Submitted: 10-Oct-2017
  • Date of Stay: October 2017
  • Source: HomeAway
Owner's Response: They were lovely guests: tidy, considerate, and pleasant to have. We ighly recommend them as guests!
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Idyllic country retreat!

  • 5 of 5

We had a wonderful stay at Deb's charming farmhouse. The house has a wonderful historic farmhouse feel. It is simply and charmingly decorated and well equipped with everything you need to enjoy a vacation on the North Fork. Even though it's on the main road, the way the house is situated really feels like you're in the country. It's a short, charming walk or bike ride to a little beach and to the village. Deb was very responsive to questions during our stay. Overall we had a wonderful time at the house and hope to return!

  • Review Submitted: 15-Sep-2017
  • Date of Stay: August 2017
  • Source: HomeAway
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Great old house

  • 4 of 5

You can't beat the location and the house itself is really charming.

  • Review Submitted: 28-Jul-2017
  • Date of Stay: July 2017
  • Source: HomeAway
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Charming, historic getaway

  • 5 of 5

This rustic and charming historic cottage in Orient is a magical place to stay. Just a short walk or bike ride to the beach on a road that was quiet enough for our 4 year old to ride his bike with us. The house has everything you need and we were impressed by the owner's loving efforts to restore this wonderful old home. You feel very comfortable while at the same time at one with the nature around you. Dinners on the deck in the evening watching the fireflies, blowing bubbles in the garden, finding hermit crabs on the peaceful local beach (potato beach), reading books on rainy days, strawberries and zucchini from Latham's farmstand were just a few of the highlights. Highly recommend.

  • Review Submitted: 28-Jun-2017
  • Date of Stay: June 2017
  • Source: HomeAway
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Charming Historic Home in Prime North Fork Location; Ample Space for a Large Family

  • 5 of 5

The owner, Deb, was wonderful and easy to work with while arranging our accommodations. We loved the history of the place and it's vicinity to the vineyards and ocean. The outdoor shower, covered in blooming wisteria, was our favorite.

  • Review Submitted: 24-May-2017
  • Date of Stay: May 2017
  • Source: VRBO, from HomeAway
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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: 24-Sep-2016
  • Date of Stay: August 2016
  • Source: HomeAway
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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

Ask Owner a Question

Additional pricing information

Pet Fee £71.02
Damage Insurance £56.11

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.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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