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Old Bay Home

North Fork Waterfront Vacation Rental Home

Quintessential North Fork farmhouse with a stunning and private sugar sand beach, large mature garden with specimen trees, waterfront and vineyard views. Seasonally available from May through Summer and Fall, including all the major US holidays celebrated throughout the Hamptons and North Fork. Enjoy this renovated NOFO home, which accommodates 8 people comfortably in 4 double bedrooms, with 2 full family baths, 2 half baths and an outdoor hot shower.

and reach out for best rates and current availability.


Please enjoy the 2 minute video below, inquire here for 2025 availability and we’ll put you in touch directly with the owner, who is now managing his rental agreements directly. We will still manage the property during your stay.


 

A fully equipped farmhouse kitchen offers cooker, fridge freezer, dishwasher, microwave, filter coffee maker, blender, toaster and plenty of pots and pans, dishes, glasses and cooking utensils etc. Open plan layout in the Dining Room, Study and Living Room, leading to a lovely 3 seasons screened porch. Laundry at Ground floor level, also a Cloakroom with half bath and an outdoor shower to freshen up after enjoying time at the beach!

The cosy Living room has a working fireplace, smart TV with Cable TV and Wifi Modem, also a study area for reading and writing.

While retaining many original features lovingly maintained by the owner, modern conveniences include Central Air Conditioning (CAC) serving all sleeping areas and updated to add a contemporary full family bathroom with glass door shower cubicle, adding to the original full family bathroom with bathtub and a Master Bedroom En-Suite half bath with basin and lavatory. There’s also a brand new powder room on the ground floor.

In addition to the Master Suite with partial water views, there are 3 additional bedrooms. The Ship Room, named for the original hand painted murals adorning the room, reflected in the chic decor. The Ship room has a Queen size bed. The other two bedrooms each have two twin (single) beds each, affording generous and comfortable accommodations for 8 guests and plenty of space for an infant cot if needed as well.

Each bedroom has a dresser, closet, bedside chair and a cooling fan in addition to the Central AC, and plenty of space for guests to read and relax in privacy. All bedrooms are stocked with 100% cotton linens, bath towels and beach towels are also available for the maximum 8 guests occupying the house. For warmth, all beds have duvets with fresh laundered covers between guests.

We’re pet friendly too!

Relax in this charming and historical setting overlooking one of the oldest vineyards on The North Fork — all this and only 400ft away to access your private beach, one of the best beaches anywhere on the North Fork or The Hamptons. Shady trees, BBQ gas grill and garden chairs add to the amenities this house offers.

Your beautiful 110ft sugar sand beach is on Southold Bay, with magnificent views towards Shelter Island. Perfect for kayaks and paddle boards, to fish, swim, or sunbathe on the calm Peconic Bay, home to some of the best oysters and clams and local fish. Browse the photos to imagine a restful and relaxing vacation in this unique east end North Fork 4 bedroom seasonal rental home.

Here are some of the repairs and upgrades to the house:

2023 New Kitchen – all new cabinets, countertops, appliances and floor.
2023 New Powder Room – basin, lavatory, pocket doors and floor.
2022 Renovated Front screened in porch
2022 Rear Deck Renovation
2021 Rear Deck Renovation
2020 Replaced Weber BBQ, beach loungers, umbrellas, outdoor chairs. Trees and hedges pruned back to enhance scenic views (waterfront and vineyard). Repairs/maintenance to front porch screens.
2019 Painted garage exterior’s east and south sides
2018 Painted 1st-floor exterior windows
2017 SE bedroom lighting, new large porcelain basin and fittings in 1st floor cloakroom.
2016 Rear patio pavers, NE bedroom lighting
2015 Chimney repair
2014 New tumble dryer, new yellow bathroom with contemporary fittings and large shower cubicle.
2013 New outdoor shower
2012 New furnace, hot water heater, fuel oil tank, sanitary & drain lines in house
2011 New roof, new dishwasher
2010 New electrical service, New cesspool

More Questions?

Send us an inquiry using the form below.

    Filed Under: Exclusives, Home-exclusive, The Old Bay Home

    FAQ The Old Bay Home

    Frequently Asked Questions About Vacation Rentals

    1. What is The North Fork like?
    2. What’s the best way to transfer from Manhattan or the airport?
    3. Do we need a car?
    4. How close is the Old Bay Home to the beach?
    5. Are the beaches private, clean and suitable for swimming?
    6. Can we bring our own boat or rent one?
    7. What phone and internet service do you provide?
    8. Why is the occupancy limited to a maximum of guests?
    9. How is the house laid out for sleeping arrangements?
    10. Is the water safe to drink?
    11. Do you allow pets?
    12. Is this a non-smoking house?
    13. What are the rates and are they negotiable?
    14. Is there any Sales tax?
    15. Are there any charges on top of the rent?
    16. What are the payment options?
    17. What is your cancellation policy?
    18. How do we proceed and when will our reservation be confirmed?
    19. What happens if there is a problem in the house that needs attention during our stay?
    20. How can I get answers to additional questions?

    1. What is The North Fork like?

    Southold Township, including the towns and areas of Laurel, Cutchogue, Mattituck, New Suffolk, Nassau Point, Peconic, Southold, Greenport, East Marion, Orient and Orient Point, is on East End of the North Fork of Long Island, New York, approximately a 55 minute drive from MacArthur Islip Airport (ISP), 1-1/2 hours from JFK International Airport and 2 to 2-1/2hours from Manhattan, depending on traffic and time of day you choose to travel.

    Long Island is shaped like a fish, with JFK airport near the eye of the fish and the North and South Forks making up the forked tail. Locally, the North Fork is known as the “Un-Hamptons”, being less developed than the better known Hamptons on the South Fork. We do not have the same crowds, traffic and price tags of the Hamptons, yet we can boast an increasing number of amenities whilst retaining the natural beauty that make it all the more attractive as a holiday venue.

    At the heart of Long Island’s Wine Country, the Township of Southold has many of the 40 or so boutique vineyards and wineries offering wine tasting, cultural and social events throughout most of the year. The area also retains many family owned and run fruit and vegetable farms offering fresh produce – the best white peaches, apples, beans, peppers, squash, zucchini, tomatoes, potatoes, broccoli and cauliflower you will ever taste.

    The North Fork is known locally as the NOFO, and comprises many small villages, each with its own unique character, and charm, also beautiful beaches and parks, historic buildings, antique shops, arts and crafts galleries, designer stores, a few fun and lively bars and wonderful restaurants for both casual, family style and fine dining. With it’s two coastlines, one on the Sound, the other on the Bay, there is a variety of beaches to chose from, some facing Shelter Island and the Hamptons, with white sandy beaches, others with high bluffs and dramatic sunsets over the rocks that face the Connecticut shoreline.

    The Old Bay Home is on the open bay facing Shelter Island, with white sandy beach and shallow water suitable for swimming, located in the desirable residential area about a mile outside the town of Southold, only a few minutes drive to Greenport Maritime Village.

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    2. What’s the best way to transfer from Manhattan or the airport?

    Many of our visitors arrive by air, from destinations including Europe and the US West Coast, and want to combine a relaxing week at the beach with time in the bright city lights of Manhattan. While we sometimes hear from departing guests that they would rather have skipped the city and spent more time with us, a combined holiday can work very well. One option is to base yourself on the North Fork and take day trips to NYC, 2 hours each way, but if you plan to do this more than once or twice during a week’s stay, you might want to split your holiday and spend a week with us followed by a week in the city, or visa versa. We appreciate that you have many choices, so the following information is simply intended as an introduction to some of the options available to you, and is not meant to steer you in any particular direction.

    Transferring to and from Manhattan. An easy way to transfer between The North Fork and Manhattan is by luxury coach, picking up a hire car locally. The trains are good, but run infrequently and involve one or two changes. With luggage, this is not a good option. Everyone, including locals, uses Hampton Jitney , which has a convenient schedule, movies and a lavatory on board, and takes 2 to 2 1/2 hours, depending on where you are staying. Click “North Fork/NYC” line for schedules and to book in advance online or by phone.

    For local car hire, Enterprise Cars has an office only a few 100 yards from the Hampton Jitney stop in Riverhead, where they will pick you up with your luggage and take you back to their office to complete the paperwork for your car. To pre-book online, enter Zip Code 11901. It’s important to note that on a Saturday, Enterprise closes at 12noon for the whole weekend, so you MUST take one of the earlier coaches to arrive around 11am if you are checking in on a Saturday. If your check-in is between Saturday noon and Monday morning, this is not an option.

    We also have Hertz Car Rentals in Cutchogue.

    From Riverhead to Cutchogue, Southold or Greenport, it’s then a simple, but very scenic drive through all the villages of about 25 minutes, and there are many interesting places to stop along the way.

    Transferring to and from the airport. The nearest international airport is JFK (John F Kennedy) in Queens. To transfer directly to Southold, we recommend that either you hire a car at the airport, or arrange to be picked up (see below), then hire a car locally in Riverhead (see above). Allow an hour and a half. The first hour is mainly LIE (Long Island Expressway), which is motorway, followed by a half hour drive through all the small villages on the North Fork. If you are not experienced with freeway driving in the US, or just want to kick back after your flight, then we recommend you take advantage of being picked up at the airport.

    Travel Tip: Whoever you use for car service, you may need a Minivan to accommodate a family of 4 with luggage rather than a normal saloon car. If a saloon car is adequate, make sure you order a “Town Car”, which is a good quality, private saloon car, the equivalent of a high end minicab service in the UK. Do not confuse this with a cab, taxi or stretch limo. It’s not the same thing. Taxis are shared by working people who do not own a car and need to go food shopping, commute to work and take their sick pets to the vet etc.. If you order a “taxi”, expect it to go on a circuitous route, picking up and dropping off others along the way, everyone squashed together with their shopping, pets etc. Do not expect it to arrive on time, or to head off in the direction you want to go. It’s not uncommon for it to break down either, so whilst this makes for an interesting experience, as a general rule, do NOT order a “taxi”!!! A “cab” is the yellow cab you hail to get around Manhattan. Yellow cabs do not serve Long Island. Although yellow cabs are available at the airport to take you to the city, if you attempt to get into one and ask them to bring you to Southold, they will tell you to get out. If not, get out anyway. You do not want to pay the fare they will charge. Just to add to the confusion, a town car is sometimes also called a “limo”, so make sure any “limo” you are offered is not a “stretch limo”, or you can expect one of those very long white cars with smoked windows that take up to 24 people, with a uniformed chauffeur, TV and cocktail bar. This will cost about $100 an hour, so unless you want to be Prom King and Queen for the day, stick with a Minivan or Town Car from Long Island Limos, and you won’t go far wrong.

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    3. Do we need a car?

    Yes, or a bicycle at least, available to rent locally. Few rentals offer stores within walking distance, so you will need a car or bicycle for a short ride into the village center and to access the food stores, restaurants, tasting rooms etc. There are many things to do, whatever the season, and in the summer, two visitor information booths offer maps and guides to suit all tastes. The nearest large town is Riverhead, where you will find a tax free designer outlet center, world class aquarium, a nearby Water park, dinosaur museum and restored Vaudeville theater, amongst other attractions. Moving east, Love Lane in Mattituck has a wonderful Cheese shop, Bakery and Candy and Chocolate Shop, a must for romantics on Valentines Weekend, or any time of year. And beyond Southold, Greenport is a bustling seaport with a historic village center, fine restaurants, sidewalk cafes, fishing charters, arts and craft galleries, antique stores, a movie theater, many historic buildings, a working Victorian Carousel and when the temperature drops below 50 degrees Fahrenheit, an outdoor ice rink. From there, you can take a 10 minute ferry ride over to exclusive Shelter Island, or continue on to magnificent Orient State Park, at the very tip of the North Fork. Whether your thing is ice sailing in the winter or taking a trip round a lighthouse in the summer, there’s always something to do on the water. For local car hire, we recommend Enterprise in Riverhead or Hertz in Cutchogue. Please scroll up for information about transferring to and from the airport and Manhattan.

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    4. How close is the house to the beach?

    That depends on the vacation rental home you pick, but the beach is never far away on the North Fork. At the Old Bay Home, it’s a short 400ft stroll through the vines to your private beach.

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    5. Is it a swimming beach?

    Yes, you will see many people swimming on the North Fork from around the beginning of June through October. In the USA, a private beach means that you own the land to the point where it is covered by water at high tide. Other people may walk the beach at low tide so far as the high water mark, but not beyond that point. In reality, few take advantage of the beach as there are many very beautiful public beaches on the North Fork. The beach is on the open bay, which has good tidal flow, but is protected from strong tidal currents by Shelter Island and the land of the twin forks. All guests swim at their own risk and are responsible for supervising their children properly.

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    6. Can we bring our own boat or rent one?

    The Old Bay Home does not have any overnight mooring, but it’s perfect for a kayak or canoe, which you are welcome to bring or rent locally. Same for paddle boards. It does not however have any amenities for overnight mooring. There is a public launch for small boats in Founders a short distance away, and may be short term moorings available at some of the local marinas, which also rent boats.

    Kayaks are available to rent locally, and they will deliver to the house and pick up, also Private Charters are available in Greenport .

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    7. What phone and internet service do you provide?

    The Old Bay Home includes Wifi and FREE local, long-distance and US calls. You may also receive incoming international calls, but the line is blocked for all outgoing international calls. WIFI Internet provider is Optimum Online. We do not provide a computer, but feel free to bring your own devices and connect anywhere in the house, it even works on the decks outside. Also, if you have “Skype” on your computer, you can make and receive international calls that way for free, and there are many other phone apps as well.

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    8. Why is the occupancy limited to a maximum number guests?

    Some vacation rentals will happily accommodate more occupants in a house of equivalent size than 8 people. We set a lower limit for good reasons. We want our guests to have the best experience, which includes enough space to be comfortableIe. Also, if you are familiar with Southold and the North Fork, then you know that we do not have municipal sewerage and that each house has its own septic system. For this reason, typically, the houses cannot cope accommodate larger groups of functions. We want you to have a problem free vacation.

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    9. How is the house laid-out for sleeping arrangements?

    All bedrooms are upstairs. There are 4 double bedrooms comprising the master bedroom suite with queen bed and half bath, guest room with queen bed and two twin bedrooms with 2 single beds in each. Add 2 full bathrooms with tub and separate cubicle shower, and there’s plenty of room for up to 8 people. We can squeeze in anadditional infant cot in any of the rooms if needed.

    It is our desire to provide guests with a comfortable living environment, and we will not accept requests to reserve for more than the maximum number of guests stated in total.

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    10. Is the water safe to drink?

    Yes, the house is supplied with town/ municipal water.

     

    11. Do you allow pets?

    Occasionally, subject to approval on a case by case basis and subject to separate Pet Contract.

     

    12. Is this a non-smoking house?

    Yes. Smoking inside any of our rentals will result in the forfeit of your deposit and immediate termination of your lease. You may smoke outside provided you dispose of butts properly in the ashtrays provided. If you smoke anywhere where there is no ashtray provided, including on the beach, please take one with you.

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    13. What are the rates and are they negotiable?

    As a guideline, you should allow $1,800 to $4,500 per week, depending on the season and number of occupants. We can rarely offer a discount unless we receive a last minute cancellation. We keep the rates extremely competitive for a vacation home with all the amenities that ours offer. In order to maintain high standards, certain “per use” costs are incurred for every rental, regardless of the time of year, the number of people, or duration of stay, but we will give you the owner’s best rate at the time of your inquiry. Rates published on this website and any listing sites on which we advertise are changeable without notice.

    14. Is there any Tax?

    If your rental is under 30 days, there is a 3% Suffolk County Short-term Rental tax payable by the Tenant.

    15. Are there any extra charges on top of the rent?

    Not if you comply with the terms of the lease and leave the house as you find it. All utilities are included in your weekly rent, also BBQ gas where applicable, phone service, TV, wifi, and trash removal. We include the cost of cleaning the house before your arrival and a normal house clean after you leave, and we provide all the linens and household towels. If you clean up the kitchen and leave the house tidy, there should be nothing else for you to pay. Extra cleaning is very rarely charged, but we reserve the right to do so if anyone leaves the house in a very messy state. The above applies to weekly rentals.

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    16. What are the payment options?

    We ask for 50% advance rent to confirm the booking, with the balance of rent and security deposit payable 8 weeks in advance of arrival. If you book 9-12 months in advance, you may spread the payments across three installments rather than two. If you book less than 8 weeks prior to your arrival, we will ask for payment in full at the time booking.

    Our preferred method of payment is by personal cheque in US$ as that does not incurr bank fees, but depending on how close to the arrival date you may be, we can handle a super-fast turnaround with payment by credit card. Credit Card fees are passed on to you.

     

    17. What is your cancellation policy?

    Should you wish to cancel at any time, advance rent paid is fully refundable, less a $200.00 processing charge, if the premises are re-rented for the same period at the same rate or higher rate, otherwise the difference is forfeit. We recommend all guests take out travel insurance and suggest sites like http://www.insuremytrip.com (no affiliation) which offer cancellation for any reason.

     

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    18. How do I proceed and when will my reservation be confirmed?

    Once the details have been agreed between us informally, we will forward a Booking Form to you by email, asking you to print this out, sign, scan and return to us, then mail together with your first payment. Your reservation is confirmed when you have received your copy of the rental agreement, signed and dated by the Landlord. We reserve on a first come, first served basis and allow a few days for you to return the paperwork to us, and in the meantime, we wait list any other inquiries. The whole process can be expedited for last minute bookings.

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    19. What happens if there is a problem in the house that needs attention during our stay?

    As property managers, we are on call for you throughout your stay. We check the house thoroughly prior to your arrival and ensure that regular maintenance is done on all appliances and systems as a matter of routine. However, with only a few hours to turn a whole house around between guests, it is possible that we could miss something that a departing guest may not have reported to us. If so, rest assured it will be fixed in a professional and timely manner. We live in the area and normally available at short notice, 24/7 if necessary.

     

    20. How can I get answers to additional questions I have?

    We are happy to answer additional questions. Please click here and send us an email,

    or phone us on +1 631 252-5653 any day up to 6pm Eastern Standard time.

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    Filed Under: FAQ Old Bay Home, The Old Bay Home

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    Cutchogue, NY 11935


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