Home Vacation Home Rentals By Owner In Greenport, NY

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Exceptional(18)

$1222.47

/ Nightly
Private Vacation Home

Greenport Getaway w/Heated Saltwater Pool- Close to Greenport Village & Wineries

Greenport, New York, United States

Welcome to this stunning & newly renovated Greenport home. This magnificent home seamlessly blends comfort, style and luxury living. The home provides a bright & airy feel throughout amongst its two levels of living. The first floor provides two spacious bedrooms and a full bathroom along with a bonus room with kitchenette that leads directly out to the backyard. Make your way to the second floor where you are welcomed by high ceilings and open concept living. A stylish living room with fireplace opens to the eat-in-kitchen and dining room with direct access to the balcony for alfresco dining. Completing the second level is a modern full bathroom, sizable bedroom, and an en-suite bedroom with a half bath.brbrKick back, relax and unwind in the private and spacious backyard that flaunts a new in-ground heated 18x36 saltwater pool with bluestone coping (NOW OPEN AS OF MAY 1, 2025). The adjacent patio offers ample space for dining and provides shade to escape the summer heat. A dedicated fire pit area is the perfect space to cozy up on summer nights, toast to memories and treat yourself to delicious s'mores.brbrLocated on the North Fork of Long Island, this home's prime location provides convenient access to all the magnificent amenities the coveted town of Greenport has to offer and is less than a mile away to Greenport Village. For the wine aficionados, spend your day at the nearby Kontokosta Winery, a waterfront winery perched atop bluff that overlooks the Long Island Sound. Looking for a beach day You have the option to spend your summer days at two nearby beaches, one private and one public. Experience the ultimate summer getaway on the North Fork.
Bed 4

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Bath 2

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Sleep 8

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Exceptional(6)

$598.67

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Private Vacation Home

American Beech in Greenport - Petite King Room 7

Greenport, New York, United States

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments. brbrOur guests pay a resort fee of $30 per night, including additional taxes at check in. brFor those looking for a cozy stay at our hotel, we have just the room for you! Room 7 is our only Petite King Room, making it our smallest king room available. This room is perfect for those who pack lightly and would prefer to spend their stay exploring the Village of Greenport and its surrounding diversions. Don’t underestimate the luxuries of this room though! After a day of wine tours, shopping and enjoying local cuisine, return to Room 7 and relax on your king sized bed wrapped in our Frette robes, pour yourself a cup of espresso from your in-room espresso machine and enjoy your favorite television shows. All of our rooms come with a fully stocked mini-bar and mini-fridge, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. Each room has robes, Frette beach towels, and heated floors to make your stay as comfortable as possible. We also provide a Nespresso machine with complimentary coffee. If there is anything else you need, please let us know! brbr Please note: In order to access this room, you are required to climb one flight of stairs — But don’t worry! We only have a maximum of 2 floors at this hotel. Free public parking is on the streets surrounding our hotel. We highly recommend parking on Bay Avenue, which is perpendicular to Main Street and has direct access to Sterling Square. Guests can shop, eat, drink, and spend the night—all within arms’ reach! Stirling Square can be quite lively at night; please consider this before booking.
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Bath 1

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Sleep 2

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$655.8

/ Nightly
Private Vacation Home

American Beech in Greenport - Deluxe King 6

Greenport, New York, United States

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments. brbrOur guests pay a resort fee of $30 per night, including additional taxes at check in. brThe ideal room in the heart of Greenport for a couple, or friends looking for an adventure! This Deluxe King suite is located on the second floor of the hotel, located right on Main Street, this room immerses you into the cool vibes and atmosphere that American Beech has to offer. Not to mention the savvy styled underground speakeasy located on the lower level. Please take into consideration before booking a room that we are located in the historic and popular Sterling Square. Therefore this area has an active night life. Nonetheless, you can enjoying our location with a selection of bars and restaurants just steps from your room. All of our rooms come with a fully stocked mini-bar and mini-fridge, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. Each room has robes, Frette beach towels, and heated floors to make your stay as comfortable as possible. We also provide a Nespresso machine with complimentary coffee, yogurt & granola to enjoy. Our bicycles and WiFi are also included in this great complimentary package! If there is anything else you need, please let us know! brbrbrbrPlease note: brbrIn order to access this room, you are required to climb one flight of stairs — But don’t worry! We only have a maximum of 2 floors at this hotel. Free public parking are on the streets surrounding our hotel. We highly recommend parking on Bay Avenue, which is perpendicular to Main Street and has direct access to Sterling Square.
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Sleep 2

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Exceptional(7)

$875.67

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Private Vacation Home

WALK TO TOWN, BEACH, JITNEY, & FISHING---No Car Necessary!

Greenport, New York, United States

Charming, in-town neighborhood. 10-minute walk to shops, beaches and fishing pier, the Hampton Jitney, LIRR and the Shelter Island ferry. In the heart of town you’ll find the supermarket, the best fresh oysters, excellent BBQ, and great ice cream. This short walk brings you to the bustling Greenport waterfront with outdoor dining and an active marina. From locally-roasted coffee and late night pizza to the Antique Carousel and outdoor concerts, these destinations are only steps away. brbr This two-story house---renovated in 2023--- has a spacious front porch with cafe table and chairs. On the first floor there is a comfortable living room with 55” flat screen TV, a lounge/office with a powder room, a sunny kitchen with dining area which accommodates six comfortably, a spacious primary bedroom with a queen bed, a full bathroom and the laundry closet with full size washer and dryer. The bright second floor has two bedrooms, one with a queen bed and the other with two twins.brbr The house is completely heated and air conditioned. br br The fully-fenced property has a large backyard with an outdoor hot&cold water shower, a 6-8 person picnic table and a gas grill.brbrThere is an assortment of games and backyard activities as well as an ample supply of beach towels and other beach paraphernalia including umbrellas, ice chest, sand toys etc. brbr A separate building, the Studio, holds a 4-person sauna with a lounge area.brbr A child’s high chair and a pack ’n play are available on request.
Bed 3

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Bath 1

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Sleep 6

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Exceptional(7)

$528.41

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Private Vacation Home

Come stay at The Whitman House a magical gem in the heart of Historic Greenport

Greenport, New York, United States

Stay in the Historic Whitman House nestled in the quaint village of GreenportbrbrStep back in time while enjoying modern comfort at the Whitman House, a beautifully preserved 1825 home in picturesque Greenport. With its rich history tied to American poet Walt Whitman and his sister Mary, who lived here after her marriage to shipbuilder Ansel Van Nostrand. Greenport, once a bustling whaling and shipbuilding hub, has transformed into a vibrant seaside village filled with charm.brbrWalt Whitman would visit Greenport for summers, using the home as a peaceful retreat. In his Letters from Paumanok he wrote about the area. His writings captured the vitality of Greenport, a busy village centered around whaling and shipbuilding and great place to unwind.brbrThis spacious, light-filled home blends historic character with bright clean modern amenities.brbr4 bedrooms (3 queens + 2 twins) – comfortably sleeps 8 guests. brbr2 full bathrooms (one on each floor) with shower, bathtub & hairdryerbrbrOriginal details: pressed tin ceilings, bead board walls, wooden floorsbrbrModern upgrades: AC, heating, WiFi, TV's and essentials providedbrbrLiving & DiningbrbrFormal sitting room with original tin walls and ceilingsbrbrCozy lounge/TV room for relaxing eveningsbrbrBrand-new eat-in kitchen with Wolf stove opens to the garden and patiobrbrOutdoor dining, BBQ grill, and a private fenced in gardenbrbrOriginal 19th-century scallop shed in the backyard, stocked with bikes, beach chairs, and umbrellas everything you need for seaside adventures.brbrJust bring your bathing suit and toothbrush—we’ve got the rest covered.brbrLocation:brbrThe Whitman House is within easy walking distance of all that Greenport has to offer:brbrBars, restaurants, shops, and cafes. brThe Village has something for everyone, local farm to table food, great sea food and oysters, an abundance of local farm stands. The North Fork is famous for its wineries, great for a day trip or grab a bottle locally.brbrThe carousel, waterfront park and numerous ice cream parlors keep all the kids happy!brbrThe Supermarket and wine shops are steps away. brSeasonal activities like indoor year round roller skating and winter ice skatingbrbrBeaches are a 5-minute bike ride or 10-minute walk to town beaches, plus stunning private beaches just a short drive awaybrbrMuch of the North Fork is flat and very suitable for cycling, if you are interested, we have bikes and helmets and we'll be happy to show you a few good spots to visit.brbrWhether you’re planning a family getaway or a friends’ retreat, the Whitman House offers the perfect blend of history, comfort, and coastal charm.
Bed 4

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Bath 2

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Sleep 8

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Exceptional(13)

$1079.69

/ Nightly
Private Vacation Home

Greenport Gem: Private Saltwater Pool, Awesome Basement, Walk to Everything!

Greenport, New York, United States

Escape to our charming Greenport Village oasis! Nestled in a quiet neighborhood just a short stroll from the vibrant heart of downtown, our spacious 2,440 sq ft home is the perfect retreat for your next getaway.brbrInside, you'll discover:brbrOpen & Airy Spaces: A bright, welcoming interior with high ceilings and a modern, open-concept layout.brGourmet Kitchen: Newly updated with stainless steel appliances, ideal for preparing delicious meals.brCozy Fireplace: Relax by the warm glow of the gas fireplace in the living room.br4 Comfortable Bedrooms: A king-sized master suite, a queen guest bedroom, a twin bedroom, and a finished basement with a queen sleeper sofa for additional guests.br3.5 Bathrooms: Three full bathrooms (two with tub/shower combos and one with a shower) and a convenient half bath.brLuxurious Amenities: Enjoy central air conditioning, a washer/dryer, and high-speed Wi-Fi.brEntertainment: Relax with Apple TV, a smart TV with Netflix and Amazon Prime, and an outdoor TV for poolside enjoyment.brOutside, your private paradise awaits:brbrSparkling Saltwater Pool: Take a refreshing dip in our heated saltwater pool, surrounded by lush greenery.brCovered Porch: Dine al fresco, sip your morning coffee, or simply unwind while watching TV on the porch.brOutdoor Shower: Rinse off after a day at the beach or pool.brExplore the wonders of Greenport:brbrSteps to Downtown: Walk to the best restaurants, shops, wineries, and the ferry to Shelter Island.brFamily-Friendly: We have a pack 'n' play and high chair available upon request.brbrDon't miss out on the chance to experience Greenport's charm from this beautiful home. Book your stay today!
Bed 3

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Bath 3

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Sleep 8

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