Home Vacation Home Rentals By Owner In Greenport, NY

Showing 20 Of 72 Vacation Rentals
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Exceptional(8)

$1241.52

/ Nightly
Private Vacation Home

Cozy Greenport village cottage

Greenport, New York, United States

Family friendly cottage, nestled in a quiet street in Greenport village. The private property has fully fenced backyard, 4 bedrooms, 4 bathrooms, wood burning fireplace, fully stocked kitchen, outdoor seating, and gas grill. The property is in a double lot with a pool and a pool-house on the second lot, secluded from the listed home. The pool/pool-house are not part of the rental.brbrThe bedroom descriptions are as follows:brbrMaster bedroom is downstairs with a king bed and an ensuite. brIn addition to a fully stocked kitchen, dining and laundry area, the downstairs also has a living room with another bathroom, TV, two sofas and access to a serene, private patio. The dining area has a wood burning stove for winter nights that warms up the dining space. brbrThere are three bedrooms upstairs with two queen beds in two rooms and a set of bunk bed (a queen and a full bed) in the third bedroom. One of the queen bedrooms have an ensuite. The other two rooms share one large full bathroom. brbrThere are two sets of stairs from downstairs to access the bedrooms upstairs. brbrThere is also an outside patio in our backyard with a bbq and patio with dining area. Plenty of greenery in our backyard provides for room for kids to play while dinner is prepared and enjoyed outdoors.brbrThe house is situated in one of a double lot property. The two lots are separated by fence and lush garden with plenty of privacy. The house is in the larger of the two lots (nearly half an acre) with a gated entrance and driveway for two cars. There is also on street parking by the fence of the property. Guests have access to everything on this one lot.brbrWe provide all linens and towels. We do not have any beach chairs and do not suggest that our towels are taken to the beach. Please bring your own beach towels, if desired. If cleaning the towels at the house, please shake sands off them outside the house so laundry machine is not damaged due to the sand.
Bed 4

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Bath 4

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Sleep 8

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Exceptional(12)

$799.75

/ Nightly
Private Vacation Home

Renovated Townhouse walk to all

Greenport, New York, United States

Discover the North Fork from our stylishly renovated 100-year-old townhouse! Perfectly located, you can walk to town, beaches, and a local brewery. This bright, airy home features a new kitchen, central AC, and a private patio with a grill. Comfortably sleeping up to 8 guests, it's the ideal base for families or groups exploring Long Island's wine country. Park your car and enjoy a walkable getaway!brOriginally built over 100 years ago, this home has been completely updated to offer a bright, airy, and stylish retreat. The open-plan main floor features a comfortable living area with a wall-mounted TV, a spacious dining room, and a brand-new, fully equipped kitchen, creating a seamless flow perfect for relaxing and entertaining. The space is filled with natural light and boasts all-new appliances and central AC for your comfort.brbrThe modern kitchen is equipped with stainless steel appliances and opens directly to the dining room and a cozy den, which provides access to the back patio.brbr**Sleeping Arrangements:**br* Master Bedroom: A very spacious room with a comfortable King-sized bed.br* Second Bedroom: A small room, located just off the master, with bunk beds.br* Third Bedroom: Features two Twin beds, one of which is a convenient Murphy bed.br* Den: Includes a Queen-sized pullout bed for additional guests.brbr**Bathrooms:**br* A spacious full bathroom with a tub and shower.br* A stylish half-bathroom is conveniently located off the kitchen.
Bed 4

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Bath 1

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Sleep 8

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Exceptional(104)

$856.88

/ Nightly
Private Vacation Home

Overlook a Vineyard, Walk to the Beach, and only a Short Walk to Town - 5 Star!

Greenport, New York, United States

Discounts available for stays 14 days. Please inquire prior to booking for details.brbrCompletely updated, modern and light-filled Cape Cod-style home. You cannot beat this location overlooking the vineyard and only a short walk to the beach or a short stroll to town. The home is beautifully decorated and professionally maintained to ensure an exceptional experience every time. Check out what our guests had to say - every one of our reviews are 5-star!brbrLONG TERM RENTAL RATES:br- Summer season (Memorial - Labor Day): $18,000br- 30 day stays: 50% rate discountbr brThe town zoning law requires that property be offered for rent for a period of no less than 14 nights. During this time period, you will have the exclusive right to occupy the property, but you may not sublet the property. No guests are allowed to be on the property unless you are also occupying the property. Please inquire if you have any questions @ 646-245-4576.brbrEnjoy dining alfresco on this beautifully landscaped 0.25 acre property overlooking the sprawling Kontakosta Vineyard; outdoor space includes a fire pit, gas and charcoal grills, and a dining table for 8. This peaceful retreat offers visitors the best that Greenport has to offer: take a quick 15 minute walk to town for dining and shopping, stroll around the corner for a waterfront wine tasting or visit the famous “67 Steps” beach located at the end of the street.brbrInside the home, relax in an open concept kitchen and dining space that includes a large chef’s kitchen with every cooking amenity you need; dishwasher, microwave, gas range and washer / dryer. The dining room has a cathedral ceiling and seats 8. The living room has a working wood burning fireplace, flat screen Smart TV, and WiFi. brbrA cozy screened porch with ceiling fan and lounge seating offers a peaceful spot perfect for morning coffee or catching up on a good book. brbrThe master bedroom with king-sized bed and bathroom are on the first floor. The second floor features two bedrooms with a king and full size bed, respectively, a sleeping alcove and bathroom with large glass shower. brbrLiving and sleeping spaces on the first and second floor have ceiling fans; window A/C units are also available from Memorial Day through Labor Day. Linens and towels included. brbrBedroom 1: KingbrBedroom 2: KingbrBedroom 3: Fullbr+ alcovebrSleeps 6brbrThe home is not ideal for toddlers and small children. brbrNo pets.
Bed 3

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Bath 2

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Sleep 6

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Exceptional(3)

$2149.61

/ Nightly
Private Vacation Home

Modern Farmhouse Private Estate, 6.5 acres

Greenport, New York, United States

Welcome to your private 6.5 acre getaway. With 4 bedrooms and 6 bathrooms, this spacious and beautifully designed home is perfect for families or couples seeking a luxurious getaway, mixing the privacy and tranquility of unobstructed farmland and the perfect location - 2 minutes from bay and sound beaches, 5 minutes from Southold and Greenport towns, farmstands and vineyards!brbrThe first floor features an open layout, with a chefs kitchen, dining room table with seating for 12 and a panoramic view of a lush 4 acre meadow. It also features a formal sitting room and cozy media room with a 70 TV and plenty of toys for all children 5 and under, 2 half bathrooms and one full bathroom, ensuring that all guests have ample space and privacy.brbrThe second floor boasts a magnificent master bedroom with an ensuite bathroom and a private terrace that overlooks the vast private field. Guests can also enjoy a queen bedroom with an ensuite bathroom, a king-size bedroom with a terrace , and a 4th bedroom that can be configured with 2 cribs or 2 twin beds, depending on your needs.brbrOur home has been designed to let in plenty of natural light, and the southern exposure means that every room is bathed in sunshine throughout the day, whether you're inside relaxing or tanning by the 40x20 gunite pool, complete with loungers and umbrellas.brbrThere's plenty of space to lounge, dine, and socialize on our spacious pool deck, which is equipped with comfortable furniture and a barbecue.brbrLocated in the heart of Greenport, our home is just a stone's throw from some of the town's best attractions, including restaurants, bars, and shops. Whether you're looking to explore the local area or simply unwind in style, our rental home is the perfect choice for your next vacation.
Bed 4

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Bath 6

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Sleep 10

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$566.62

/ Nightly
Private Vacation Home

Beachy Craftsman Cottage—Fire Pit, Music & Walkable Location

Greenport, New York, United States

Welcome to your perfect North Fork getaway in Greenport—a charming 1903 Craftsman cottage that blends historic character with modern comfort. Nestled in the heart of this vibrant seaside village, our home offers a relaxed, walkable escape where you can leave the car behind and fully unwind.brbrThis cozy three-bedroom, 1.5-bath home comfortably sleeps up to six guests and is thoughtfully designed for easy, breezy living. Enjoy central air-conditioning on warm summer days, and rinse off after the beach in the refreshing outdoor shower. Evenings are best spent gathered around the fire pit under the stars, sharing stories and making memories.brbrInside, the cottage invites you to slow down and savor the moment. With its warm, cozy vibe and artistic touches, it’s a perfect retreat for families, couples, or friends. Music lovers will feel especially at home—guests are welcome to enjoy the piano, guitar, and ukulele for a spontaneous jam session or a quiet evening of creativity.brbrWhether you're seeking a peaceful beach escape, a charming small-town experience, or a creative retreat, this one-of-a-kind cottage is ready to welcome you.brbrALLERGY FRIENDLY: I keep a gluten and soy free kitchen and can set aside separate cooking tools if you need. The kitchen is not nut-free, though I rarely use peanuts. There are very light rugs and curtains around the house to cut down on dust and pollen. Central air conditioning offers relief from seasonal allergies.brbrDOG FRIENDLY: There is a fenced dog run to keep your puppy safe and happy. My little one likes to sit in the sun, dig and zoomie!
Bed 2

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Bath 2

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Sleep 3

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Exceptional(4)

$1919.37

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Private Vacation Home

Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families

Greenport, New York, United States

Greenport Cove ContemporarybrbrSpacious North Fork Home in Greenport, Heated Pool, Perfect for Familiesbrbr4BR/3.5BA: private heated pool, outdoor dining, gas BBQ, work-from-home space, multiple sitting and dining areas, sunroom, hot tubbrbrWelcome to your perfect escape from the hustle and bustle of everyday life, a stunning contemporary beach house located in the heart of the North Fork in Greenport. This inviting retreat boasts an open floor plan and features four spacious bedrooms and 3.5 luxurious bathrooms, accommodating up to eight guests comfortably. As you step inside, you'll be greeted by a spacious and bright interior that exudes warmth and comfort, with multiple sitting and dining areas designed to bring family and friends together. This is the perfect haven for families seeking a relaxing getaway, offering an expansive deck for outdoor dining, where you can savor your meals while taking in the serene surroundings.brbrThe exterior amenities of this beach house are nothing short of spectacular, ensuring total privacy for your stay. The expansive deck is a highlight, complete with a dining table and multiple sitting areas perfect for enjoying cocktails and unwinding in the fresh air. Imagine spending your afternoons lounging by the private heated pool, surrounded by the beauty of nature. The expansive yard offers plenty of space for outdoor activities, and there is ample free parking available for your convenience. Whether you're looking to relax in the sun or enjoy a leisurely swim, the outdoor amenities cater to all your needs, providing a tranquil and luxurious environment.brbrStep inside and embark on a tour of this exquisite home, where an open layout and plenty of natural light create an inviting atmosphere. The living spaces flow seamlessly from one room to the next, making it easy to transition from the cozy living room to the elegant dining room and the gourmet kitchen. The kitchen is a chef's dream, equipped with top-of-the-line appliances and a coffee maker, perfect for brewing your morning cup of joe. The living room features a fireplace, adding a touch of warmth and ambiance, while a dedicated work-from-home space ensures you can stay connected if needed. With multiple sitting and dining areas, including a charming sunroom, there is no shortage of places to relax and enjoy the company of your loved ones. Modern conveniences such as Wi-Fi, a washer and dryer, and central air conditioning are provided to enhance your stay.brbrThe bedrooms and bathrooms in this beach house are designed with your comfort in mind, offering fresh linens and all the essentials you need for a restful night's sleep. Each bedroom is thoughtfully decorated, creating a serene and welcoming environment where you can unwind after a day of exploration. The bathrooms are equally luxurious, featuring modern fixtures and ample space to pamper yourself. Whether you're staying in the master suite or one of the guest bedrooms, you'll find everything you need to feel right at home.brbrConveniently located close to the charming town of Greenport, this beach house offers easy access to a variety of attractions. Explore the nearby town of Southold, visit multiple wineries and farm stands, and indulge in the local cuisine at the many restaurants in the area. Art galleries and antique shops add to the charm, providing plenty of opportunities for shopping and cultural experiences. Whether you're looking to relax by the beach, explore the local towns, or enjoy the vibrant arts and culinary scene, this contemporary beach house on the North Fork is the ideal destination for your next vacation.brbrThis property has a max occupancy of 8brbrBedroomsbrbrPrimary Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in ClosetbrbrBedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, Streaming TV, Walk-in ClosetbrbrBedroom 3: One Queen Bed, 2nd Floor, Air Conditioning, Streaming TV, Walk-in ClosetbrbrBedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard ClosetbrbrBathroomsbrbrPrimary: Full Bath, 2nd Floor, Ensuite, ShowerbrbrBathroom 2: Full Bath, 2nd Floor, Ensuite, ShowerbrbrBathroom 3: Full Bath, 2nd Floor, Shower/Tub CombobrbrBathroom 4: Half Bath, First Floor/Main FloorbrbrTVsbrbrPrimary Bedroom 1: StreamingbrbrBedroom 2: StreamingbrbrBedroom 3: StreamingbrbrBedroom 4: StreamingbrbrOutdoors & Pool/SpasbrDeck/Patio (Covered), Grill (Gas), Outdoor Shower (Hot + Cold Water), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Fence Around The Pool, Fence Around The Yard, Beach Chairs, Private Pool (Heated, Outdoor, Freshwater), Hot Tub (Freestanding Hot Tub)brbrAmenitiesbrBed Linens, Usable Fireplace (Wood-Burning), Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Hair Dryer, Iron/Ironing Board, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot, Keurig), Dishes and Silverware, Pots and Pans, Toaster, Speaker System (Bluetooth Speaker), Television (Main Living Room), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Smart TV, Ice Maker, Laptop-Friendly Workspace, Hot Water, Blender, Gym/Fitness Room (Weight Training Equipment, Stretching / Yoga Mat), Essentials, Electric Vehicle ChargerbrbrLocationbrbrNearby Beaches:brHOA Beachbr67 Steps BeachbrSandy BeachbrSouthold Town BeachbrbrNearby Grocery Stores:brIGA GreenportbrbrNearby Restaurants and Bars:brClaudio's WaterfrontbrLucharitosbrGreenport Harbor Brewing CompanybrKontokosta WinerybrCroteaux WinerybrbrOther Location Information:brInlet Pond County ParkbrbrSuitability: Not handicap accessible.brPrimary renter must be at least 30 years old.brbrPet Policy: One dog of 80 lbs or less is permitted for an additional $250.00 per booking. Dogs over 80 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire).brbrUtility Disclaimer: Utility fees are included in the total rental amount. Guest shall be responsible for the costs associated with excessive usage of utilities during the term of the Reservation.brbrCleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense.brbrAdditional Guests: Additional guests are prohibited unless express approval is provided.brbrEvents Policy: Events are prohibited unless express approval is provided.brbrSpecial Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed.brbrPool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking.brFor energy conservation purposes, the pool heater may only be operational from 8am to 6pm.brbrHot Tub Disclaimer: The hot tub is open year round.brbrOff-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.brbrPayment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Marquis will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners'). Should Marquis be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Marquis is notified in writing 72 hours or more prior to the start of the reservation.brbrNote: All payments must be made prior to check-in.brbrVRBO charges the guest directly for their service fee and applicable taxes, while StayMarquis charges separately for the rental rate. As a result, you will see two separate charges at the time of booking-one from VRBO and one from StayMarquis.brbrIf there is a second installment, it will be collected directly by StayMarquis shortly after the first installment.brbrPayment Method: Balance payments made with credit card are capped at $3,500. Payments over $3,500 shall be made by check, ACH or wire.brbrSecurity Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement.brbrThe guest experience for this property is managed by StayMarquis, a local vacation rental management company. By booking this property, you will receive a dedicated Guest Experience Manager who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property.brbrShowings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.
Bed 4

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Bath 3

Bath

Sleep 8

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Exceptional(3)

$954.13

/ Nightly
Private Vacation Home

Charming 3-bed/2-bath beach house with water views - steps from beach

Greenport, New York, United States

Welcome to Greenport's cozy beachside retreat – a charming 3BR/2BA cottage steps from 5th Street Beach and walkable to Greenport Village. Enjoy water views in bedrooms, a dreamy clawfoot tub, a large backyard with a garden, and vintage-meets-modern charm throughout. Perfect for beach days, wine nights, and cozy escapes.br✔ Water views in bedroomsbr✔ Steps to 5th St beachbr✔ Two Large and comfy living areas for entertaining and relaxingbr✔ Eat-in kitchen and separate dining area br✔ Large and comfy living areasbr✔ Walkable to town & LIRRbr✔ Spacious backyard with gardenbr✔ High-speed WiFibr✔ Smart TVbr✔ Central Cooling and HeatingbrbrThis is an old home from the early 1900s that has some modern updates. We've kept most of the character of this charming old home. Please note that the staircase is slightly narrower and steeper than most modern homes. brbrThere is a video doorbell located near front door on this property.brbrDisclaimer: By booking this property, you agree that the owners and hosts are not liable for any accidents, injuries, illnesses, theft, or loss that occur during your stay. You acknowledge that you are responsible for your own safety and the safety of your guests. The property is privately owned, and the hosts reserve the right to refuse service to anyone. By accepting this reservation, it is agreed that all guests are expressly assuming the risk of any harm arising from their use of the premises.
Bed 3

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Bath 2

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Sleep 6

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