Vacation Home Rentals By Owner In Greenport, NY

Set in the historic section of Greenport village, the Captain’s House, built in 1820, is an elegant and charming 3 bedroom, 2 bath home ready to enjoy, especially for a summer getaway or a cozy holiday retreat. It's a 3 block walk into town and a short bike ride or drive to all the area beaches, wineries and treasure finding. brbrThe Captain’s House is in the perfect location for those who’d like to leave the car at home and wander into town to visit shops, wine bars and restaurants. It's even a 10 minute walk from or the Jitney/train. brbrThere are three bedrooms (one with a queen bed, one with 2 twins or king and a smaller 3rd bedroom with a full bed) and two full bathrooms, one with a washer/dryer that is on the ground floor. There are two comfortable living rooms, one with a fireplace and large color TV with Netflix, Amazon Prime, Smart TV as well as a selection of puzzles and board games for all ages. There is a TV in the master bedroom as well. Attached to the living room is a formal dining room with a farm table that seats 8 for those chilly or hot evenings better spent inside.brbrFor the ultimate chef, the home has a fully stocked kitchen with Cuisinart appliances, a Garland stove, every utensil imaginable as well as all dining-ware. There is no need to bring sheets, towels or beach towels, it’s all here. For those with small children, note that I do not toddler-proof the house, remove the nicknacks, etc. so keep that in mind when renting! brbrThere is a very large and beautifully landscaped backyard complete with a 'Secret Garden hidden in the far back of the property overlooking a zen fountain. Attached to the house is a back deck with a charcoal and a gas grill and an outdoor garden shower. Dining al fresco with friends and family a the patio dining area allows room for entertaining.brbr* PLEASE NOTE: Beaches are open to renters with permit. I would need to notarize a rental permit, so please let me know in advance if you would like to get one. It is $40 and the name on the agreement needs to match the registration. I have also included some beaches that do not require a permit.

1820 Whaling Captain's Home - A walk to a coffee or cocktail!

Greenport, New York, United States

3

Bed

Bath

5

Sleeps

$1190.79

PLEASE READ FULL DESCRIPTION! Rental registry # 0952brPrivate modern 4 bedroom/2 bath cabin near the bay situated on 3.8 acres on cul-de-sac. The cabin is set 200 ft off a quiet cul-de-sac that lies across the street from Gull Pond. Separated on three sides by no less than 3 acres of woods and Northfork beauty. 50% of property is backed by over 10 acres of nature preserve. Property is filled with amazing song birds as well as deer and wild turkey. It is truly a nature lover’s sanctuary! brbrPublic golf course is right across Sound Ave as well as walkable to a local winery and some great restaurants.brGreat family vacation house. br5 min drive to maritime village of Greenport and less to bay/sound beaches. Outdoor security cameras on premise. brNew property… keep an eye for updated pictures! brbrNEW *****Inground saltwater heated pool****br br7 person Hot tubbrbrAir hockey and foosball tables brbr2 separate TV rooms. brbrWill not rent without first having contact and discussion with potential tenant. brbr ** Copy of Photo IDs for adults is required to rent this property. brSeparate lease is required for long term rental. br brNO instant bookings will be accepted. br****Please read! br14 day Min stay requirements- please ask before bookingbrbrSpecial woodland living near the water.brbrRates- brPlease refer to calendarbrDiscounts given for long term rentals- 30 days or morebr brNew York State rental tax, and Suffolk County hotel tax will be collectedbrPreference is given to long term rentalsbrbrPriority given to LONG TERM summer season inquiries. DISCOUNT available for 30 day or longer.

Secluded 4-bedroom house with AC in charming Greenport

Greenport, New York, United States

Bed

Bath

Sleeps

$640.81

Greenport GetawaybrbrNewly built ranch, beautifully landscaped with pool, large yard, patio, fire pit, ample seating, minutes to private beachbrbr3BR/2BA: open floor plan, wood-burning fireplace, gourmet kitchen, spacious bedrooms, pool tablebrbrWelcome to your summer home at Greenport Getaway! Surrounded with manicured landscaping and outdoor entertainment, this newly built ranch home is centrally located near local beaches and shops. Whether youre seeking relaxation or full-scale entertainment, you are equipped for every mood. Perfect for a family or friend retreat, enjoy light-filled, open spaces for entertaining with ease of flow throughout. Gather by the fireplace on cooler evenings and jam to your favorite tunes from the sound system available. Prepare your favorite meals whether casual or formal from your well-equipped kitchen featuring stainless steel appliances, granite countertops and a large center island that doubles as a breakfast bar. Gracefully extending to the rear deck, take your meals outdoors or dine together from the formal dining table. Three serene bedrooms and two full baths complete this home with comfy beds, large closets, plush towels, and fresh linens. Enjoy bubble baths from the soaking tub available in the Primary suite. Head outside for additional entertainment as your spacious backyard features a new 20' x 40' heated pool, expansive patio with ample seating plus a fire pit for those serene evenings under the stars. Gently tucked along the North Fork, enjoy the allure of the Hamptons blended with a laid-back ambiance and small town feel. Conveniently located just minutes to a private beach, relax with your favorite book as you sink your toes in the sand!brbrThis property has a max occupancy of 6brbrBedroomsbrbrBedroom 1: One King Bed, First Floor/Main Floor, Air Conditioning, Ensuite Bathroom, Streaming TV, ClosetbrbrBedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning, ClosetbrbrBedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, ClosetbrbrBathroomsbrbrBathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower, TubbrbrBathroom 2: Full Bath, First Floor/Main Floor, Shower/Tub CombobrbrTVsbrbrBedroom 1: StreamingbrbrOutdoors & Pool/SpasbrDeck/Patio, Patio Furniture (Table, Chairs), Grill (Gas), Fire Pit (Wood-Burning), Cooler, Lounge Chairs (4 Chairs), Fence Around The Yard, Private Pool (Outdoor, Heated)brbrAmenitiesbrBed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Usable Fireplace (Wood-Burning), Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Other, Pot), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Cable TV, Smart TV, Speaker System (Bluetooth Speaker), Gym/Fitness Room (Treadmill), Garage (1 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Parking (3 Cars In Driveway), Laptop-Friendly Workspace, Pots and Pans, Pool TablebrbrOther FAQ'sbrbrEstimated Square Footage: 1,650brbrAccess to private beach within walking distancebrPool will be installed by June 2022brbrSuitability: Not handicap accessible.brPrimary renter must be at least 25 years old.brbrPet Policy: Pets are strictly prohibited at this property.brbrUtility Disclaimer:brUtility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $95.00 per night of the reservation.brbrCleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest's expense.brbrAdditional Guests: Additional guests are prohibited unless express approval is provided. An additional guests fee of $50.00 per person per night may be required.brbrEvents Policy: Events are prohibitedbrbrSpecial 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.brbrWhile StayMarquis manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, StayMarquis will provide you with a Guest Experience Manager who can help facilitate any request, from grocery shopping to organizing a private chef.brbrGuest Experience: This property is part of our 'Elite' program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed.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.

Newly built ranch, beautifully landscaped with pool, large yard, patio,...

Greenport, New York, United States

Bed

Bath

Sleeps

$1096.8

NO EXTRA FEES FOR CLEANING, EXTRA GUESTS & AMENITIES! brbrRelax in one of America's most beautiful seaside villages, historic Greenport. Walk to the village and within minutes to vineyards, Lavender farm, golf and beaches also Shelter Island and Orient Point Ferries. Take the Hampton Jitney or LIRR from the city and walk to our breathtaking home.brElegant and located on Captains Row in the Greenport Historic District. Elegantly built for the wealthiest banker on the North Fork. Largest property in National Historic District in Greenport Village. The backyard is truly special, private with pergola and outdoor grill perfect for dining under the stars and our new giant chess set is sure to please.brLovingly restored to its original elegance and authentic Classic Queen Anne Victorian. This is a complete modern home with new kitchen and bathrooms. This home has been the subject of many artists!brEnter this home and feel the impeccable carpentry work with its rich patina. Magnificent 5 foot single pocket siding doors that separate the formal rooms glide with your fingertips. Top of the line kitchen appliances. New luxury linens, mattresses and romantic brass and iron beds. Feel the elegance of the bygone era. There is even a small library and doll house room. All lighting is exquisitely original, restored and sets the mood. Any celebrations are to be enjoyed by our overnight renters only. brPlease do not plan any events with our property in mind.brPlease do not plan to do entertainment cooking here. This is a historic house and we encourage outdoor dining or light meals. Sadly, no frying allowed in our home.brbrWe are compliant with local laws and there are minimum stay requirements.brFor special consideration, please email us. Weekend rates apply to holidays.brWe will try our best to accommodate you and create a wonderful experience!

Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach

Greenport, New York, United States

Bed

Bath

8

Sleeps

$1741.01

Serene Greenport BeachousebrbrRelaxing Greenport Escape with a Fenced Pool, Private Beach with Mooring for Boatersbrbr4BR/2.5BA: Fence Around the Pool, Private Beach Access, Outdoor Shower, Bicycles, and PatiobrbrNestled on a quiet private block in the charming seaside town of Greenport, this inviting 4-bedroom, 2.5-bath home is the perfect North Fork getaway for families and friends. Designed as a single or two-family beach house, it comfortably sleeps 9, with an additional TV/playroom in the basement featuring a queen pull-out sofa for extra guests and added hangout space.brbrThe home offers a flexible bedroom setup ideal for families and groups, including one bedroom with a twin-over-twin bunk bed and another with a twin-over-double bunk bed. Bright, welcoming interiors and an open layout make it easy to gather, relax, and enjoy time together. The kitchen is well-equipped for easy meals at home, while the living and dining spaces create a comfortable setting for everything from morning coffee to casual evenings in. Additional conveniences include Smart TVs, Bluetooth speakers, high-speed WiFi, a washer and dryer, and plenty of room to spread out. A fireplace and wood stove add to the home's cozy character and charm.brbrOutside, the home is made for summer living. Enjoy the fenced pool, enclosed outdoor shower, outdoor firepit, two hammocks, and plenty of space for lounging and dining outdoors, creating a fun and family-friendly backyard retreat. A new BBQ grill makes outdoor cooking and entertaining even easier.brbrOne of the homes standout features is its proximity to the pristine waters of August Acres Private Association Beachjust a 5-minute walk or quick bike ride away. Four bikes are provided, along with a fully stocked beach cart/wagon loaded with chairs, umbrellas, sand toys, and beach essentials. A stand-up paddle board is also included, making beach days easy, active, and memorable. The nearby beaches are known for their calm, sandy waters, ideal for families. For boating enthusiasts, the home also includes access to a private boat mooring located just off the private association beach, offering a rare and convenient way to enjoy the North Fork by water.brbrPerfectly situated between two of the North Forks most sought-after towns, the home is just a 5-minute drive to both Greenport and Southold. Guests can easily explore local shops, restaurants, bars, farm stands, markets, and vineyards while returning home to a peaceful, private setting at the end of the day.brbrWhether you're planning a beach vacation, a family getaway, or a laid-back North Fork escape, this home offers the ideal blend of comfort, outdoor living, and unbeatable location.brbrThis property has a max occupancy of 9brbrBedroomsbrbrBedroom 1 - Ensuite: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Standard ClosetbrbrBedroom 2: One Bunk Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrBedroom 3: One Bunk Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrBedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrBathroomsbrbrBathroom 1 - Primary Ensuite: Full Bath, 2nd Floor, Ensuite, ShowerbrbrBathroom 2: Full Bath, 2nd Floor, Shower/Tub CombobrbrBathroom 3 - Half Bath: Half Bath, First Floor/Main FloorbrbrOutdoors & Pool/SpasbrBicycle (4 Adult Bikes), Deck/Patio (Uncovered), Outdoor Shower (Hot + Cold Water), Fence Around The Pool, Beach Chairs, Beach Umbrella, Paddle Board, Lounge Chairs (4 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fire Pit (Wood-Burning), Private Pool (Outdoor)brbrAmenitiesbrBed Linens, Air Conditioning (Central Air), Dryer, Internet (Wifi), Washer, Garage (Attached), Living Room, Parking, Bath Towels, Microwave, Coffee (Pot), Toaster, Television (Main Living Room, Media Room), Kitchen, Carbon Monoxide Detector, Smoke Detector, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Ice Maker, Privacy (Partially Private), Heating, Hot Water, Dishes and Silverware, Private Entrance, Essentials, Wood Stove, Speaker System (Bluetooth Speaker)brbrLocationbrbrNearby Beaches:br67 Steps BeachbrSandy BeachbrbrNearby Grocery Stores:brIGA GreenportbrbrNearby Restaurants and Bars:brClaudio's WaterfrontbrLucharitosbrGreenport Harbor Brewing CompanybrKontokosta WinerybrbrOther Location Information:brInlet Pond County ParkbrbrOther FAQ'sbrbrPool Fenced In: YesbrbrBackyard Fenced In: NobrbrSuitability: Primary renter must be at least 28 years old.brbrPet Policy: Pets are strictly prohibited at this property.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 end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest's 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.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.brbrWhile StayMarquis manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, StayMarquis will provide you with a Guest Experience Manager who can help facilitate any request, from grocery shopping to organizing a private chef.brbrGuest Experience: This property is part of our 'Elite' program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed.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.

Relaxing Greenport Escape with a Fenced Pool, Private Beach with Mooring...

Greenport, New York, United States

Bed

Bath

Sleeps

$679.5

HAMPTONS-STYLE LUXURY WATERFRONT RENTAL — STIRLING COVE, GREENPORTbr180° panoramic bay views • Every room faces the water • Boat slip included; pool, pickle ball, brExperience summer on the North Fork in a rare, one-of-a-kind waterfront residence in coveted Stirling Cove—where every room is framed by shimmering bay views and the scenery feels like a private resort.brUpstairs, two serene bedroom suites each feature a private full bathroom; one full bathroom downstairs. Shared deck with second bedroom. upstairs open to the bay, creating the perfect backdrop for morning coffee and golden-hour sunsets. A washer and dryer upstairs adds effortless convenience.brDownstairs, uninterrupted water views from the living and dining spaces. A premium American Leather convertible sofa with an orthopedic mattress offers elegant guest accommodations, and a newly renovated full bathroom with shower completes the layout (three full bathrooms total). Step outside to two separate waterfront decks—one off the living room and one off the dining room—where you’ll enjoy the constant parade of sailboats and yachts just beyond your railing.brStirling Cove’s amenities elevate the lifestyle: boat slip, tennis and pickleball courts, and an award-winning pool that juts into the bay—all just two blocks from the heart of Greenport, known for its charming boutiques and remarkable restaurants.brIncluded: Utilities, Internet & TV, BBQbrMax Occupancy: 6 total (including children)brCleaning: Bi-weekly + final cleaningbrDeposit: $10,000 due upon signing leasebrAugust: $21,0006brSeptember: $13,000

Incredibly Unique waterfront townhouse w stunning views from every room. Pvt

Greenport, New York, United States

Bed

Bath

Sleeps

$723.58

Luxury 2 bedroom, first floor apartment located across the street from Townsend Manor Marina in the heart of Greenport Village . Walk to town and enjoy the amazing restaurants and shopping that Greenport has offer. This custom Victorian Farmhouse has been fully renovated with all modern amenities.brbrThe custom gourmet kitchen has a sub zero refrigerator, Wolf stove, farmhouse sink. Gas grill located outside where you can enjoy evening dinner under the stars.brbrYou will find 2 Flat screen SMART TVs. There is Wifi throughout the house.brbrThe large wrap around deck is the perfect spot to have your coffee or glass of wine with marina views and great people watching. brbrThe first floor apartment is bright with sunshine and hard wood floors. Easy to maintain for beachside living. brbrThe airy master bedroom has a Samsung smart flat screen TV. Enjoy a great nights sleep on the temperdic King Size bed.brbrThe guest bedroom has a queen size bed as well as a gorgeous wood barn door. brbrThere is a full bathroom, laundry in the apartment and an outdoor shower in the private backyard.brbrThe driveway can fit 3 cars and the home has plenty of public parking in front and behind.brbrThis apartment has it all. Under 1 mile from the fifth street public beach. 1/2 mile to the Commuter station - train, bus, ferry is located walking distance to restaurants, shopping and bars. Close to wineries

Brand new 2 bedroom, Greenport Village, walk to town Marina Views!!

Greenport, New York, United States

Bed

1

Bath

6

Sleeps

$1411.38

One of the nicest spots on the North Fork (that's a quote from a knowledgeable local!), beautifully designer-renovated beach house. 3 bedrooms, 2.5 baths, sleeps 6.brWater views from 3 sides of the house, and all bedrooms have water views. Beautiful, large lawn and panoramic water views of Peconic Bay, Shelter Island, and Greenport Village. brbrBuild a sandcastle on your own 100-foot-wide private beach or relax on the bayfront patio. You can bike to one of the nearby fresh produce farm stands, or to either of two charming villages (Greenport and Southold) . Browse through antique shops, pick up a beach read at the local indie bookstore, ride the carousel, and indulge in the foodie culture of the North Fork. 50 vineyards are within 20 miles, and specialty food shops and restaurants abound. Orient State Park is within a few miles, and offers nature lovers' breathtaking views of birds and marshes, beaches and bays. brbrThe private and spacious house is recently renovated and new to the market. With central A/C, two patios, off-street parking and a garage, this comfortable, chic home is an ideal getaway. brThe 1st floor includes: br• Living room with French doors and windows on 3 sides has waterfront views, built-in window seat with water views, extra-long comfy sofa (great for naps!), and non-working fireplacebr• Spacious and fully equipped open-plan kitchen has double sink, granite countertops, custom tile work and new stainless steel appliances.br• Dining room has large farmhouse table that seats 12 and custom chandelierbr• Den/Library has 40” smart TV, large library of books, games and movies, extra-long sofa and comfy chairs. French doors open onto a brick patio with a wisteria covered pergola.br• Powder room/half bath has pedestal sink and toilet.br• Gorgeous cherry wide-plank floors throughout first floor, and in hallways of second floor. Bedrooms are carpeted.br• Mudroom/entry hall has vintage encaustic tile flooring, built-in window seat with baskets beneath for shoes, and round captain’s windowbrbr2nd floor includes: br• Master suite with French doors to private Juliet Balcony with stunning view of the lawn, beach and water; King-size bed; wall-mounted smart TV; walk-in closetbr• Master bath has custom marble tiling and marble counter tops with triple vanity mirror, separate glassed-in shower and extra-deep luxury spa tubbr• 2nd bedroom has queen-size bed with water views from both sides; spacious closet; 2 comfy chairsbr• 3rd bedroom has double bed, built-in window seat with water view, double closetbr• 2nd full bath has shower in extra-long tub and marble-topped vanitybr• Laundry Room has large-capacity washer and dryer, folding counter, and rack for air-drying clothes, swimsuits, etc. brbrOutdoor amenities include: br• Water-facing brick patio with large teak table and 6 teak chairsbr• 2nd outdoor patio with wisteria-covered pergola and water views has Italian wicker café table and 4 chairsbr• Outdoor showerbr• Gas Grillbr• Hammockbr• Rope swingbr• Large lawnbr• Kitchen herb gardenbrbr

Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views

Greenport, New York, United States

3

Bed

Bath

6

Sleeps

$1147.62

Winter Harbor House is a stylish Victorian walking distance from the best restaurants, bars and beaches in Greenport Village. Absolutely perfect location. Only a few hundred feet from the Mitchell Park and Marina Waterfront Boardwalk/Beach and the North Ferry to Shelter Island. Enjoy gorgeous marina views and great people watching from the front porch. This 1890's Victorian has all the modern amenities you want while making you feel like you're experiencing a part of Greenport's history.brThe spacebrWell preserved 1890's Victorian that we polished up with some modern amenities while preserving the unique period features. The main floor is designed for socializing. Two living areas; one with a 55'' TV and fireplace, the other with a turntable and chest of classic LP's. Newly updated kitchen and separate dining area are perfect for family meals or just to warm up before hitting the amazing restaurants in the North Fork.brOne of the four bedrooms is also on the main floor and there is a full bathroom off the kitchen.brUpstairs there are three bedrooms, all with en-suite full bathrooms. One has a King bed with water views, one a Queen with water views and one a Full over Full bunk with a Twin trundle. We also have a pack and play for your adventurous little one. The fourth bedroom is on the main floor and has a Queen bed, water views and a full bathroom a few steps away.brThe house is dramatic, cozy and very well lit with both ambient and spot lighting on dimmers in all the main rooms. Wifi is strong throughout the house. The 55'' TV in the living area and the TV in the main bedroom have apps for all the major content providers like Netflix, Amazon, Hulu etc. as well as live TV via YouTube TV. For music lovers there are Sonos speakers throughout the house.brThe Kitchen has been updated with new appliances, cabinets and all the modern cooking supplies you will need. We also have a drip coffee maker and a Keurig. In the back yard there is a gas grill.brGuest accessbrThere is a large driveway with enough parking for at least 4 cars and there is also parking on the road.

Elegant Victorian in the Heart of Greenport

Greenport, New York, United States

Bed

Bath

13

Sleeps

$949.03

*30 day minimum rental*brRenovated modern farmhouse on a spacious property with a large heated saltwater pool and plenty of privacy in the large backyard. Designer quality furniture throughout the entire house, Sealy Posturpedic mattresses. New kitchen appliances with dishes, kitchenware, and luxury accessories in fully stocked kitchen (Vitamix , Cuisinart, coffee maker, Cangshan knives, and full range of cookware/bakeware). Open and bright first floor with 65 4K UHD TV and Sonos sound system in first floor living room. Formal dining room with table seating 8. Third floor TV and game room with plenty of space to relax or entertain (also perfect for kids). Front and side porch with seating, lighting, and fans perfect for summer evenings. Back patio and pool area has high end outdoor furniture including dining table for 8, lounge area with couch and coffee tables, swivel chairs, 4 chaise lounges for poolside relaxation, and an outdoor shower. Half a mile walk to Eastern Shores private association beach, one mile walk to hidden gem 67 Steps Beach, just over one mile to Greenport Village center with dining, shops, carousel, and ferry.brbr1 King Bed in master bedroombr2 Queen Bedsbr1 Full Bedbr2 Twin Bedsbrbr2 Full Bathrooms with shower and tubs, 1 Half BathroombrbrHigh capacity Washer and Dryer in basement

North Fork Summer Family Retreat, Heated Pool, Walk to Beach, New Furnishings

Greenport, New York, United States

Bed

Bath

Sleeps

$385.92

Newly-renovated! And location can't be beat. Home on the same block as the Greenport Village beach, and a short walking distance into town. Perfect setup for a family, wedding group, couples getaway, friends get-together, or folks visiting North Fork for weddings / wineries.

Beach Block Hideaway

Greenport, New York, United States

Bed

Bath

Sleeps

$564.25

Come stay at The Owl's Nest for your next trip to the North Fork. You'll have a hoot! Walking distance to everything Greenport has to offer. Conveniently a 12 min walk or 6 min drive to the Greenport Train and Jitney stop.

The Owls Nest

Greenport, New York, United States

Bed

Bath

Sleeps

$959.68

Welcome to the Village Villa—a newly renovated, spacious 3-bedroom home nestled right in the heart of Greenport Village.brbrLocated just steps from beloved local restaurants, the grocery store, and a wine and liquor stores. A short walk to Front Street’s vibrant selection of coffee shops, breakfast cafés, award-winning restaurants, boutiques, bars, the Greenport Marina, and Mitchell Park—you’ll be perfectly positioned to enjoy everything the Village has to offer.brbrOutdoor SpacesbrStep outside to a shaded front porch—perfect for sipping coffee and watching the village come to life. The property also features a long, wide driveway with space for multiple vehiclesbrbrBedroom Layoutbr- 1 King Bedroombr- 2 Full (Double) BedroomsbrbrGuest AccessbrGuests can enter through the front door. The home is equipped with a keyless electronic lock on the front door. You’ll receive an access code before your arrival for a smooth, contactless check-in.brbrbrOther things to notebr- The top and bottom floor share no common spaces and have completely separate private entrances.br- The backyard is reserved for 1st floor guests onlybr- The garage is not accessible to guests for vehicles but can be used for bike storage upon requestbr- 5-minute drive or 20-minute walk to 5th Street Beach (no parking pass required).br- 5-minute drive or 10-minute walk to the Greenport Train Station, Hampton Jitney stop, and Shelter Island Ferry.brbrWhether you're planning a weekend getaway, a wine country adventure, or a family vacation, the Village Villa Top Floor offers the ideal home base in one of Long Island’s most charming and walkable towns.

The Village Villa Top Floor–Renovated 3-Bed in the Heart of Greenport Village

Greenport, New York, United States

Bed

Bath

Sleeps

$1710.67

Welcome to the Village Villa—a newly renovated, spacious 6-bedroom home nestled right in the heart of Greenport Village. With two full kitchens and two bathrooms, this property is ideal for families or groups seeking comfort, convenience, and charm.brbrLocated just steps from beloved local restaurants, the grocery store, and a wine and liquor store. A short walk to Front Street’s vibrant selection of coffee shops, breakfast cafés, award-winning restaurants, boutiques, bars, the Greenport Marina, and Mitchell Park—you’ll be perfectly positioned to enjoy everything the Village has to offer.brbrSleeps up to 13 guestsbrbrOutdoor SpacesbrStep outside to a private backyard patio strung with twinkling lights—an ideal setting for morning coffee, al fresco dinners, or relaxing under the stars. Enjoy meals at the umbrella-shaded dining table in a peaceful, tucked-away setting.brbrThe property also features:br- A long, wide driveway with space for multiple vehiclesbr- A spacious, grassy side yard—great for lawn games or relaxing in the sunshinebr- A shaded front porch—perfect for sipping coffee and watching the village come to lifebrbrBedroom LayoutbrMain Floorbr- 1 King Bedroombr- 1 Full (Double) Bedroombr- 1 Twin (Single) Bedroombr- 1 Sleeper Sofa (Double)brbrUpstairsbr- 1 King Bedroombr- 2 Full (Double) BedroomsbrbrGuest AccessbrGuests can enter through the front door to access the upstairs or the side door at the top of the driveway to access the main floor. The home is equipped with a keyless electronic lock on the front door. You’ll receive an access code before your arrival for a smooth, contactless check-in.brbrOther things to notebr- The garage is not accessible to guests for cars but can be made available for bike storage upon request.br- There is no interior stair case that links the upstairs and downstairs apartments. Both have private outdoor entrances. br- 5-minute drive or 20-minute walk to 5th Street Beach (no parking pass required).br- 5-minute drive or 10-minute walk to the Greenport Train Station, Hampton Jitney stop, and Shelter Island Ferry.brbrWhether you're planning a weekend getaway, a wine country adventure, or a family vacation, the Village Villa offers the ideal home base in one of Long Island’s most charming and walkable towns.

The Village Villa – Renovated 6-Bedroom Home in the Heart of Greenport Village

Greenport, New York, United States

Bed

Bath

Sleeps

$1030.4

Welcome to the Village Villa 1st Floor—a newly renovated, spacious 3-bedroom home nestled right in the heart of Greenport Village.brbrLocated just steps from beloved local restaurants, and the grocery store. A short walk to Front Street’s vibrant selection of coffee shops, breakfast cafés, award-winning restaurants, boutiques, bars, the Greenport Marina, and Mitchell Park—you’ll be perfectly positioned to enjoy everything the Village has to offer.brbrOutdoor SpacesbrStep outside to a private backyard patio strung with twinkling lights—an ideal setting for morning coffee, al fresco dinners, or relaxing under the stars. Enjoy meals at the umbrella-shaded dining table in a peaceful, tucked-away setting.brbrThe property also features:br- A long, wide driveway with space for multiple vehiclesbr- A spacious, grassy side yard—great for lawn games or relaxing in the sunshinebrbrBedroom Layoutbr- 1 King Bedroombr- 1 Full (Double) Bedroombr- 1 Twin (Single) Bedroombr- 1 Sleeper Sofa (Double)brbrGuest AccessbrGuests can enter through the side door, towards the middle of the driveway. The home is equipped with a keyless electronic lock on the front door. You’ll receive an access code before your arrival for a smooth, contactless check-brin.brbrOther things to notebr- The 1st floor and top floor units have no shared spaces and have completely private separate entrances.br- The backyard is reserved for 1st floor guests only.br- The garage is not accessible to guests for cars but can be made available for bike storage upon request.br- 5-minute drive or 20-minute walk to 5th Street Beach (no parking pass required).br- 5-minute drive or 10-minute walk to the Greenport Train Station, Hampton Jitney stop, and Shelter Island Ferry.brbrWhether you're planning a weekend getaway, a wine country adventure, or a family vacation, the Village Villa 1st Floor offers the ideal home base in one of Long Island’s most charming and walkable towns.

The Village Villa 1st Floor—Renovated 3-bed in the heart of Greenport Village.

Greenport, New York, United States

3

Bed

1

Bath

7

Sleeps

$794.06

Located in Greenport, this house is a dream for families or groups seeking a tranquil getaway. With four bedrooms featuring a king, queen, full, and twin bed, guests find plenty of space to unwind. Two bathrooms with showers male getting ready a breeze! The living areas create a delightful atmosphere where everyone can relax comfortably. Whether you’re gathering for meals or enjoying quiet moments, this home offers an enjoyable retreat. Kickback, relax, and enjoy everything Greenport and our house has to offer. brAn easy and comfortable home base for families or groups of friends in the heart of the North Fork! Walk to town, drive minutes to the beaches and wineries, and enjoy a private pool and fire pit. Eclectic decor and thoughtful touches throughout. Featuring a front porch, fully equipped kitchen, pool and fire pit. Enjoy all season living in this home away from home just a 10 minute walk to The LIRR station, Hampton Jitney, and The North Ferry.

greenport pool retreat! 4 bedroom home dog friendly! & fully fenced

Greenport, New York, United States

Bed

Bath

Sleeps

$1633.77

Same location I have two 2 cottages that sleep 4 each . See VRBO search bar [Where To] with the Listing ID 173361 and the Listing ID 167288.brbrThe centerpiece of this family owned waterfront estate, “The Main House” is a neo-victorian 5-bedroom, 3-bathroom sauna room and outdoorshower charmer that comfortably sleeps 8 - 10 people. brbrThe panoramic porch with stunning water views, the spacious living room, the large dining room and kitchen and expansive outdoor patio and deck make this vacation paradise one of a kind. brbrWhether you’re planning a family reunion or looking to escape to the natural wilderness of the North Fork, this house has it all. Stroll along the estate’s private beach or have picnic overlooking the water. brbrThe beautiful tree filled grounds are complete with pristine views of the bay and Shelter Island. With room to roam and nature to explore, the property is both kid and pet friendly. The house is fully furnished and linens are provided. brbrThe house is quiet and secluded, yet within easy walking distance to Greenport Village, offering the best of both worlds. brbrWith a strong nautical history, Greenport is a water-lover’s paradise and the perfect destination for sailing, boating, fishing, swimming, kayaking, and canoeing. Mitchell Park Marina is just a short walk from the estate and provides transient slips by the day or week. brbrPlease call in advance for reservations to secure your spot. brbrWhile downtown in the village of Greenport, explore the local boutiques and stores. Take advantage of the history-rich Railroad, Stirling–Ireland House, and East End Seaport museums. brbrRide the antique carousel, or take a tour of the harbor on The Glory, an electric launch. Sample the local bounty from land and sea in a variety of restaurants offering casual fare to award-winning dining. brbrTour the over 42 vineyards located here on the North Fork. Discover the art galleries featuring local and international artists who represent the contemporary to the classic. So much tucked into one square mile and all conveniently within walking distance! brbrGreenport's proximity to Manhattan, Connecticut, and the South Shore means you don’t have to go far to get away. Enjoy a casual drive from the city, or let the LIRR or Hampton Jitney carry you here stress free. brbrEither way there is something for everyone, so come and experience what makes Greenport charming and unique. For more information about Greenport and all it has to offer, please visit the official village website supported by the Greenport BID. Make sure to enter Greenport Village in your search. brbrThe estate also offers additional accommodations that when combined can be perfect for family gatherings. Please visit listing #173361--and--167288brbrbrKeywords: House

Beach/Waterfront 7.2 ac Estate with Dockage -40 ft

Greenport, New York, United States

Bed

Bath

Sleeps

$757.86

Beautifully appointed townhouse in coveted Stirling Cove Condominiums. Enter a light filled room with magnificent views of the cove and bay. Featuring newly renovated, spacious kitchen, dining room, elegant living room with wood burning fireplace, water view deck, and powder room. Second floor has master bedroom suite with expanded, renovated bath and private water view balcony. A guest room with private bath and laundry complete the floor plan. Unit comes with a private boat slip in the protected basin with easy access to the cove and bay. Complex offers heated in-ground pool, tennis courts, private beach - all just a short walk to Greenport Village restaurants, shopping, and grocery. Near Islands End golf course and access to all that the North Fork has to offer. Full-time on-site management. Inquire with host for reduced rates or one month stay or longer summer specials.

Exquisite Waterfront Townhome in Greenport with Pool and Boat Slip. Walk to all!

Greenport, New York, United States

Bed

Bath

Sleeps

$454.55

Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, outdoor studio/bedroom, private parking, a kayak, bicycles, public swimming dock at end of block, and is one block from the charming seaside village of Greenport, NY. We are located 95 miles east of New York City on Long Island's North Fork with 5 minute walking access to NY city bus and train. Great small restaurants & a terrific micro brewery are 1/2 block away.

Architect Designed Home in Waterfront Village

Greenport, New York, United States

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Bath