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Historic vineyard farmhouse with fabulous sandy bay beach

Bedrooms 4
Half Baths2
Property type farmhouse
Minimum Stay 7 nights


Half Baths
Minimum Stay
7 nights

About the property

4 bedrooms, 2 full bathrooms, 2 half bathrooms, outdoor shower, sleeps 6 to 8

Charming turn of the century farmhouse with forever vineyard views only a short 400ft stroll through the vines to your sugar sand beach on the Peconic Bay with views of Shelter Island. Bring kayaks, or rent some, fish, bbq, swim and relax in lovely landscaped gardens with mature trees, sipping wine while overlooking the vines where the grapes are grown. One of the best sandy bay beaches with beach chairs and loungers provided for guests.

Inside the house, all 4 bedrooms are on the second floor, which has air conditioning (CAC, not window units). The master bedroom with quality Queen bed, separate sitting area and half bathroom, has partial water views to the private beach on Peconic Bay. The Ship Room, with hand painted vintage wall art also has a Queen bed. Two front bedrooms benefit for two twin beds in each add flexibility to the home's sleeping arrangements. There are two full bathrooms upstairs - the original family bathroom with bathtub and shower over, and a second full bathroom, with large shower cubicle was added in 2014. A cloakroom next to the laundry downstairs and an outdoor enclosed shower with hot and cold water add to the comfort and enjoyment of the amenities this home offers.

The private garden overlooks the vines and offers both shady and sunny areas to read and relax, sunbathe, BBQ and enjoy dining outdoors on either the covered deck or the enclosed porch. One mile to the nearest food store, close to farm stands and fishmonger for fresh local seafood. There are many local wineries to visit in the area.

Read what some of our prior guests have said about this home.

Guest Reviews: "Our family had a fabulous time in Southold! The property is spectacular & we enjoyed spending a lot of time outside & on the beach. Thank you so much for everything - we will be returning." Sicignano Family

"We really liked the house. We loved the property and the walk through the vineyard because it's so peaceful and relaxing. The house is so clean and big. Thank you so much." DiPenta family.

"We loved this place & everything about it. It was perfect for our family of 6. Beautiful property, vineyards, so close to the beach. House was very clean and had everything needed and more. Wine and fresh flowers were a nice touch. We will be back. Thank you." Shuman family.

"The Weinkaufs & Klass families had a fabulous time at the Old Bay Home. Loved the beach, the yard, the East End, everything. See you next year!"

"The Lane family had a terrific time! Beautiful location & lovely home. Thank you Joanna and Dennis for being so helpful."

"We've all had a wonderful time here on the North Fork. This home is really beautiful, and the yard and grounds....and the beach were all so wonderful. It's unbelievable to step out onto the back porch for breakfast, and look across the vineyards. Or to peak through the gate toward the beach, surrounded by so much peace and quiet. The private beach is beyond words."

"Our daughters (9 & 6) really enjoyed the mini-train ride on the north edge of Greenport, as well as the carousel there, right on Rte 25. They also were thrilled with the Atlantis Marine World Aquarium in Riverhead. It's a top notch facility with great exhibits.

And we ate well while we were here too. Most of our meals were cooked right here - lots of grilling, fresh vegetables (incredible corn) from local farms, and great clams, scallops and flounder from Brauns Seafood Market (about 15 minutes west on 25, south side of the road). It will be tough to leave tomorrow." The DeBenedittis Family, NYC

"We had the most wonderful time in The Old Bay Home here in Southold. We simply felt at home and were so lucky with the weather. Una and Aima did their little drawings for your guest book, Lulu and Terra will do the next ones when we all come again, hopefully! Nick was very happy here too, cooking for his family and we all thank you very much for a perfect holiday." Barbara, Lisina and family,



Professionally managed by Property Angels of Cutchogue.

More Details

Property Manager
Joanna Lane, Property Angels, Licensed RE Broker, Cutchogue NY
Member since: 2009
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
September 12, 2016


5/5 -
(2 traveler reviews)

Historic vineyard farmhouse with fabulous sandy bay beach
average rating of 5.0 based on 2 reviews

An enjoyable stay at the Old Bay Home.

  • 5 of 5

Wonderful home, just as peaceful and comfortable as a farmhouse in a storybook! Let's see:

THE HOUSE: Clean as a whistle; roomy; well laid out; lots of bathrooms; nice deck and porch, garage; big; comfy bedrooms. The premises are kept in perfect conditions.

THE BEACH: The water was clear and warm and at night the stars were endless. See the Observatory in town.

GREENPORT: Quaint and fun; lots of shops and good places to eat. We saw a wonderful live concert on the Green.

SOUTHOLD: Lots of farm stands with lots of fresh veggies locally grown. We attended a car show and had a blast.

WINERIES: Many, many of those, all different; each with fine wines of all types and tastes and sun filled settings.


Water (jet ski, fishing, kayaking etc.) all easily procured locally.

Golf - 'nough said!

Shopping - for the girls and guys.

Biking - safe and fun

Sightseeing - Shelter island is nice to check out.

I forgot all the things to do, there were so many! Thank you Joanna and Dennis, good job!

  • Submitted: Sep 16, 2016
  • Stayed: Aug 2016
  • Source: HomeAway
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Lovely Family Home

  • 5 of 5

We had such a great time at the Bay Home. The kids loved sitting on the terrace and having deer and rabbits stroll in and out of the well kept garden. This is our fifth stay at this cozy home and we hope to be back again.

Since last time there is an additional new bathroom with shower and modern toilet. I personably still prefer to use the outdoor shower. It is so lovely set under the big tree.

We did a few outings. Of course visited the next door Old Field Vineyard which has a lovely lawn to sit and taste their wines besides chicken and a goose.

We went riding in Mattituck at Highwind Farm. Fantastic instructors there. We also went wake boarding and water tubing with Peconic Bay Watersports who are just down the road from the house and we had an excellent dinner at the best restaurant on Long Island, the North Fork Table and Inn which is just down the road too.

All in all a very relaxing and good energy holiday.

  • Submitted: Jul 14, 2015
  • Stayed: Jul 2015
  • Source: HomeAway
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Nearest Airport
40 Miles
Islip MacArthur
Nearest Barpub
1 Miles
Nearest Ferry
7 Miles
Nearest Golf
3 Miles
Islands End Golf
Nearest Train
1 Miles
Southold LIRR
Nearest Motorway
18 Miles
Long Island Expressway LIE at Riverhead
Nearest Restaurant
1 Miles
North Fork Table and Inn
Nearest Beach
On site
Car: recommended

The North Fork of Long Island boasts the majority and the best of the vineyards in Long Island Wine Country. A rural countryside setting with many farms, cultural and artistic events may be enjoyed, fresh farm produce at the roadside stands, many organic growers. Fine dining or family style, there are many fantastic choices with local seafood specialities as well as increasing amount of locally raised poultry and other meat, cheese and other artisan delights. The area is known also for its sandy beaches, boating, pretty villages and as a friendly resort area where a relaxing vacation can be enjoyed throughout the year and it's never over crowded. There are numerous festivals, holiday and special events, including Southold Village July 4th parade, Greenport's Maritime Festival in September and Columbus Day. Easy access to both the Hamptons on the South Fork and Manhattan for day trips.

Other Activities: wine tasting, wine tours, Victorian carousel, swimming, kayaking, birdwatching


Rates & Availability

Enter dates for accurate pricing

Additional information about rental rates

End of stay Cleaning $200
Tax Rate 3.0%

Owner is authorized to collect Suffolk County Short-Term Rental Tax of 3% on all rentals of less than 30 days. Minimum rental 14 days per Southold Town Code. Call for more information. Security Deposit: 10%, which is refundable if the house is left as found subject to contract. Weekly Rental Rates include Wifi, basic cable TV, phone, linens and towels, beach towels, duvets for cooler season, central air conditioning (CAC), utilities, BBQ gas, trash removal. Discounts available for rentals of 1 month or more. Call or email for details!

To confirm a booking, we ask for signed contract and 50% holding deposit, the balance paid 8 weeks before arrival. If you book within 8 weeks, the total amount is due at the time of booking.

Cancellation Policy: All advance monies are fully refundable less a $200 administration charge if the property is re-rented for the same rate or higher rate, otherwise the difference is forfeit.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.
Available arrival
Available stay (no arrival)
Calendar not updated in over 2 months and may not be available. Look for rentals with Request to Book or updated calendars.


Southold Farmhouse Accommodation and Amenities

Property Type:
  • farmhouse
  • Guests provide their own meals
  • Housekeeper Included
Floor Area:
  • 1800 sq. ft.
Location Type:
  • Beach ...
  • Beach View ...
  • Beachfront ...
  • Downtown ...
  • Near The Ocean ...
  • Resort ...
  • Rural ...
  • Water View ...
  • Waterfront ...
  • Away From It All
  • Family
  • Activities Guide
  • Air Conditioning
  • Alarm Clock
  • Basic Soaps
  • Broadband Access
  • Clothes Dryer
  • Fireplace
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Parking Off Street
  • Shampoo
  • Telephone
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Blender
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher
  • Freezer
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Child's Highchair
  • Dining Area
  • seating for 8 people
  • 2 Bathrooms
  • 2 Half Baths
  • Bathroom 1 - toilet , ensuite to Master Bedroom
    Bathroom 2 - toilet , combination tub/shower , 2nd floor
    Bathroom 3 - toilet , 1st floor
    Bathroom 4 - outdoor shower , hot and cold
    Bathroom 5 - toilet , shower , New for 2014 on the 2nd floor
  • Hairdryer in full bathroom
  • 4 Bedrooms, Sleeps 8
  • Master ensuite - 1 queen , with sitting room and half bath
    The Ship - 1 queen
    Twin 1 - 2 twin/ single
    Twin 2 - 2 twin/ single
  • Travel cot (Portacrib) and high chair available on request at no extra charge. The house also has removable stair gates.
  • Books
  • Books for Adults
  • Books for Kids
  • DVD Player
  • Satellite / Cable
  • Television
  • VCR
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Screen Porch / Veranda
  • Small Cooler
  • Unscreened Porch / Veranda
  • Walkway to Water
  • Wood Deck
  • 6 garden chairs
  • 6 beach chairs
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible
Onsite Services:
  • Chauffeur
  • Housekeeper
  • Massage
  • Private Chef
  • autumn foliage
  • bay/sound
  • churches
  • cinemas
  • duty free shops
  • library
  • live theater
  • marina
  • museums
  • restaurants
  • synagogues
  • water parks
  • winery tours
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • horseback riding
  • outlet shopping
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • equestrian events
  • fishing
  • golf
  • hiking
  • hunting
  • ice skating
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
Enclosed outdoor shower with hot and cold water.

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