Home Vacation Rentals By Owner In Greenport, NY

Showing 110 Of 110 Vacation Rentals
Slider Thumb
Exceptional(7)

$828.82

/ Nightly
Private Vacation Home

Luxury North Fork Saltbox, Near Greenport Village, Wine Country & Beaches

Greenport, New York, United States

The Saltbox Greenport – Historic Charm in the Heart of the North ForkbrbrThe Saltbox Greenport is a thoughtfully restored 19th-century Saltbox vacation home located just minutes from Greenport Village in the heart of North Fork wine country. This historic home blends old-world character with modern comfort, creating a warm and stylish retreat for exploring the best of Long Island’s North Fork, from vineyards and beaches to farm stands, restaurants, and waterfront attractions.brbrStep inside and experience original wide plank floorboards from the 1800s, curated décor, and cozy fireplaces that create a relaxed, design-forward atmosphere after a day exploring nearby wineries, beaches, and village shops. The kitchen and bathrooms have been fully updated while preserving the home’s historic charm, offering clean, stylish, and practical spaces for real stays, not just photos.brbrThe open layout makes it easy to gather, cook, unwind, or spread out and recharge with friends and family.brbrPerfect for wine weekends, beach escapes, family gatherings, and relaxing North Fork getaways.brbrLayoutbrbr• 2 bedrooms + sitting room with additional sleeping space available by request only (extra charge)br• 2 full bathroomsbr• Fully stocked kitchenbr• Living room with fireplace (not in use March–September)br• Patio and private yardbr• Seasonal hot tub (Memorial Day Weekend – Labor Day Weekend)br• Fire pit (summer–fall)brbrWalkable Greenport LocationbrbrYou are staying right on Main Street in West Greenport, which means you can walk almost everywhere:brbr• Restaurants, bars, shops, and galleriesbr• Local North Fork vineyards nearbybr• 67 Steps Beach – just 0.4 miles awaybrbrNo driving required, no planning logistics, just park and enjoy the village.brbrExtrasbrbr• EV / Prius charger (available by request at reservation)br• LGBTQ+ owned and operatedbr• Dog Friendly (pet fee)br• Comfortable furniture designed for actual lounging, not stagingbrbrMore photos and details:brhttps://www.thesaltboxgreenport.com/brbrPlease Read Before BookingbrbrThis is a true close-to-town Greenport location. You are staying in a lively North Fork vacation area near beaches and vineyards that attract many visitors. This is not a secluded countryside retreat, and there will be activity and noise, especially during peak seasons.brbrIf you’re looking for complete silence, this may not be the right fit.brIf you want walkability, charm, and an authentic Greenport experience, it’s exactly that.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(79)

$1128.05

/ Nightly
Private Vacation Home

Greenport Getaway the perfect blend of relaxation, nature, and North Fork charm.

Greenport, New York, United States

Charming Family Getaway with Heated Pool, Private Beach Access & Kayaks in Greenportbrbr5 Bedrooms • 4 Bathrooms • Sleeps 10 • Heated Saltwater Pool • Walk to BeachbrbrWelcome to your perfect escape in the beautiful maritime town of Greenport, NY. This spacious, family-friendly colonial sits on a private ¾-acre lot and was designed with comfort, connection, and quiet in mind.brbrWhether you’re lounging by the heated saltwater pool, exploring local wineries, or kayaking along the serene coastline, this home offers something for everyone.brbr✨ What You’ll Love About This Homebrbr • ‍♀️ Heated Saltwater Pool – Relax, unwind, and swim in total comfort.br • Four Kayaks Included – Two single and two double kayaks ready for your coastal adventures (please bring your own life vests).br • Private Beach Access – Just a 10-minute walk away. Calm, shallow waters are ideal for paddle boarding or splashing with kids.br • Comfortable Accommodations – 5 cozy bedrooms, 4 bathrooms, perfect for up to 10 guests.br • Near Top Wineries – Explore North Fork’s world-renowned wine scene just minutes away.br • Spacious Backyard – Grill, play, or stargaze in a peaceful setting.br • Fully Equipped Kitchen & Laundry – Everything you need for a carefree stay.brbr Important to Know Before You BookbrbrThis home is best suited for families or quiet groups seeking a peaceful escape. To maintain a calm and respectful environment for all:brbr • Quiet hours begin at 10 PM – especially in the backyard. Elderly neighbors live nearby and value a peaceful evening.br • No loud gatherings, parties, or events – if you’re planning something high-energy, this home is not a fit.br • Please carpool – limited parking, and neighborhood prefers low vehicle traffic.br • Guests must take their trash with them – Greenport requires use of yellow town garbage bags (available at local waste yard). Recyclables must be separated.brbr Location Highlightsbrbr • 10-min walk to private beachbr • 10–20 min drive to wineries, restaurants & shopsbr • 2-hour drive from NYCbrbrBook your serene Greenport retreat today and enjoy the perfect blend of relaxation, nature, and North Fork charm.
Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(2)

$870.48

/ Nightly
Private Vacation Home

Cozy Greenport Cottage | House in Greenport with a private pool & sauna

Greenport, New York, United States

Cozy Greenport CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to Maple Street Manor, managed by Vacasa. This house is located in Greenport but your 24/7 support is always nearby.brbrThis house features 3 bedrooms and 2 bathrooms with space enough for 10.brbrPlease review our property photos and our available amenities to make sure this rental is a perfect fit for your needs. We strive to keep this information as up-to-date as possible so you can feel confident in knowing what you are renting.brbrWe will send you all necessary pre-arrival and check-in information after booking. This can include guest instructions, notices, and other helpful information.brbrWhat We LovebrProviding the ultimate spot for privacy, relaxation, and indulgence this beautiful home is surrounded by trees on all sides and features a heated pool and firepit. When you aren't taking invigorating dips into the turquoise water of the pool, rinse off under the outdoor shower, and head inside to continue to enjoy picturesque views from the home's ample windows. brbrBoasting an open-concept layout, the living room, dining area, and kitchen blend together perfectly. Sit back on the soft sofa in the living room while streaming your favorite shows from the large TV. When hunger arises, walk steps away into the gleaming, full kitchen. Equipped with granite countertops, a center island, and stainless steel appliances - this space makes cooking a breeze! Show off your culinary skills here before serving your dishes to your loved ones at the adjacent wooden dining table. When you don't want to cook, a quick walk into town will lead you to popular Little Creek Oysters and 1943 Pizza. brbrThe bedrooms in the home are equally lush and light-filled. Remote workers will appreciate the two designated work areas complete with external monitors. Rest assured that getting ready each morning will come easily in one of the home's spacious and updated bathrooms. brbrAdditional interior perks include a fitness room equipped with a Peloton in the basement, a sauna, an additional kitchenette and seating area with pull out couch in the pool house, a private washer/dryer, and air-conditioning throughout the main house. brbrHouse RulesbrThere is free parking for 3 car(s).brCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brStreaming tv available with guest's own login.brVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: Ring doorbell at the front door. brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(2)

$667.9

/ Nightly
Private Vacation Home

Updated and dog-friendly, close to seasonal activities with yard, & washer/dryer

Greenport, New York, United States

Modern on 9thbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrOriginally an old-time candy and soda shop this 1957 home is truly a charmer. Recently updated with modern touches, find yourself enjoying a beautiful vacation in Greenport, New York at this beloved home. Close to wonderful wineries, local beaches, lavender fields, pumpkin patches, and even holiday tree farms, there is an abundance of activities to enjoy regardless of the season! During your stay check out the Sparkling Pointe Vineyards & Winery (six miles), Pindar Vineyards (seven-and-a-half miles), Orient Beach State Park (less than 12 miles), and the Elizabeth A. Morton National Wildlife Refuge (43 miles). Shelter Island Ferry Greenport is less than a mile away and 67 Steps Beach is two miles away.brbrLight, bright, and inviting, when you find yourself back at your stay after a day spent out on the town, rest assured that you will feel comfortable. An open floor plan allows for easy, shared conversation as the chef in your family prepares a tasty meal in the kitchen. A truly gorgeous kitchen features marble countertops, ample prep space, and stainless steel appliances. Access to central air-conditioning and a cozy fireplace ensures that regardless of the temperature outside, inside is perfect. Appreciate the delightful art pieces scattered throughout the open hallways and rooms of your stay, each a perfect fit for the overall aesthetic. The primary bedroom offers another warm fireplace, as well as a large walk-in shower, and double sinks. For your total convenience, a private washer/dryer is available in the home. Walk outside to find a spacious, private backyard, perfect for enjoying a glass of wine, a meal, or a family game night. Bikes provided for your exploring pleasure are parked in the backyard and await your use. brbrDon't miss out on this lovely and modern, perfect for any season, stay! brbrTHINGS TO KNOWbrHigh chair available for use.brStreaming services are available to guests.brVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 2 vehicles.brbrSecurity camera details: On the front of the house pointed across the entrance. brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(1)

$769.17

/ Nightly
Private Vacation Home

Modern home in Greenport, close to beaches, outdoor dining, perfect for families

Greenport, New York, United States

Please note that a reservation for this property needs to be approved before it is confirmed.brbrGreenport Coastal RetreatbrbrModern home in Greenport, close to beaches, outdoor dining, perfect for familiesbrbr2BR/1.5BA: modern kitchen, outdoor deck, outdoor dining, gas BBQ, walkable to beaches, fenced in yardbrbrNestled in the charming village of Greenport, this modern and updated home offers a luxurious escape for sophisticated travelers seeking relaxation, adventure, and the ultimate North Fork experience. Ideally situated on a private block, this stunning two-bedroom, one-and-a-half-bathroom retreat comfortably accommodates up to five guests. Its prime location is just moments from the towns renowned beaches, parks, and wineries, making it the perfect haven for couples, families, or small groups looking to unwind in style.brbrUpon arrival, guests are welcomed by a beautifully landscaped property that offers total privacy. A fully fenced-in backyard provides a serene oasis, complete with multiple seating areas designed for both quiet morning coffees and lively evening cocktails. The expansive deck features an elegant outdoor dining setup, where guests can savor farm-to-table meals or enjoy a glass of local wine under the stars. A gas BBQ invites effortless al fresco dining, while the lush greenery and peaceful ambiance create the perfect backdrop for memorable gatherings. For those arriving by car, the home boasts ample free parking, ensuring a stress-free stay.brbrStep inside to discover an inviting open-concept living space bathed in natural light. The airy and thoughtfully designed floor plan allows guests to flow effortlessly from one area to the next. The spacious living room features a plush, oversized sectionalideal for cozy movie nights or afternoon reading sessions. Adjacent to the living area, a charming breakfast nook provides a delightful spot to sip morning espresso. The sleek, fully equipped kitchen is outfitted with modern appliances, a coffee maker, and all essential cookware. Whether preparing a gourmet meal or a simple snack, every culinary need is met. The stylish island and adjacent dining space are perfectly suited for hosting intimate dinners or casual brunches with friends and family. High-speed Wi-Fi, central air conditioning, and the convenience of a washer and dryer ensure a seamless and comfortable stay.brbrGuests will find two beautifully appointed bedrooms designed for rest and rejuvenation. The primary bedroom exudes elegance with its plush queen size bed, fresh linens, and thoughtfully curated decor. The second bedroom features full size bunk beds, making it ideal for families or close friends. Each room is equipped with ample storage and soft lighting to create a warm, restful ambiance. The renovated full bathroom boasts modern fixtures, fluffy towels, and all the essentials needed for a refreshing start to the day. A convenient half-bath adds an extra touch of practicality to this well-appointed home. For some extra sleeping space, there is a foldable murphy style bed available in the den.brbrBeyond the comfort of the home, guests will find themselves in the heart of Greenports vibrant coastal scene. Just a short walk away, an array of charming boutiques, art galleries, and award-winning restaurants await. Stroll along the historic streets and discover local favorites like Noahs, The Frisky Oyster, and Little Creek Oyster Farm & Marketeach offering an unforgettable dining experience. For those eager to explore the area's natural beauty, the pristine beaches of 67 Steps and Inlet Point Park are mere moments away, perfect for sunbathing, paddleboarding, or simply taking in the breathtaking waterfront views. Wine enthusiasts will delight in the proximity to North Forks acclaimed vineyards, including Kontokosta Winery, where they can indulge in tastings while admiring sweeping Long Island Sound vistas. Whether its biking through the scenic countryside, embarking on a sailing excursion, or perusing the bustling farmers' markets, this exceptional retreat offers something for every traveler.brbrThis property has a max occupancy of 5brbrBedroomsbrbrBedroom 1 - Primary: One Queen Bed, 2nd Floor, Air Conditioning, Streaming TV, Standard ClosetbrbrBedroom 2 - Bunk Beds: One Bunk Bed, 2nd Floor, Air Conditioning, Streaming TV, Standard ClosetbrbrDen - Foldable Bed: One Murphy Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, PrivacybrbrBathroomsbrbrBathroom 1 - Half: Half Bath, First Floor/Main FloorbrbrBathroom 2 - Full: Full Bath, 2nd Floor, Shower/Tub CombobrbrTVsbrbrBedroom 1 - Primary: StreamingbrbrBedroom 2 - Bunk Beds: StreamingbrbrDen - Foldable Bed: StreamingbrbrOutdoorsbrDeck/Patio (Uncovered), Grill (Gas), Patio Furniture (Table, Chairs, Umbrella), Fence Around The YardbrbrAmenitiesbrBed Linens, Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Living Room, Parking, Bath Towels, Microwave, Coffee (Pot), Dishes and Silverware, Pots and Pans, Toaster, Television (Main Living Room), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Smart TV, Ice Maker, Laptop-Friendly Workspace, EssentialsbrbrLocationbrbrNearby Beaches:br67 Steps BeachbrSandy BeachbrbrNearby Grocery Stores:brIGA GreenportbrbrNearby Restaurants and Bars:brClaudio's WaterfrontbrLucharitosbrGreenport Harbor Brewing CompanybrKontokosta WinerybrbrOther Location Information:brInlet Pond County ParkbrbrSuitability: Primary renter must be at least 21 years old.brbrPet Policy: One dog of 50 lbs or less is permitted for an additional $250.00 per booking. Dogs over 50 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.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.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 2

Bed

Bath 1

Bath

Sleep 5

Sleeps

Home Most popular vacation rentals in Greenport