Vacation Home Rentals By Owner In Greenport, NY

Showing 40 Of 72 Vacation Rentals

$1222.47

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

Bath

Sleeps

Exceptional(6)

$598.67

/ Nightly

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

Sleeps

$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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Bath

Sleeps

Exceptional(8)

$1100.16

/ Nightly

Private Vacation Home

The Lucky Oyster Est 1886 3 Bd / 2 Ba Historic & Walk to Town

Greenport, New York, United States

Located steps from town, this historic gem is perfect for a weekend getaway. With a spacious kitchen, living and dining spaces as well as a back yard perfect for entertaining and easy walking access to all the best Greenport has to offer, you’ll love the lucky oyster just as much as we do!

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Sleeps

$1154.31

/ Nightly

Private Vacation Home

Waterfront house on steerling harbor, views from every room.

Greenport, New York, United States

Fully furnished monthly, summer or year round rental on Sterling Harbor with spectacular views out to Bay. A five minute walk to downtown Greenport. This stunning 3 bedroom, 4 bath home boasts hardwood floors, lots of windows and a gourmet chef's kitchen with granite counters. Floating dock/boat slip directly in front may be available under separate agreement. Surrounded by vineyards and farm stands, come enjoy the North Fork.

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Bath

Sleeps

Exceptional(19)

$750.93

/ Nightly

Private Vacation Home

Beautiful condo on the Long Island Sound in a resort

Greenport, New York, United States

This condo is one of the nicest decorated in Cliffside. Gorgeous shiplap walls with navy accents. It has a beautiful fireplace, new deck and much more. This unit has the capabilities to be handicap accessible. The master bathroom has a queen size bed and private bath. The second bedroom has 2 twins and also a private bath. The sectional in the living room opens up to a full sleeper making this condo able to sleep 6 people. All rooms have flat screen tv's.br Being on the property of the Cliffside Resort makes this an excellent choice for a getaway. There is a heated pool and clubhouse on property. They have Bar-B-Q's for your use. This resort is located on the Long Island Sound and equipped with lounge chairs for your use. The Cliffside Resort has many activities morning yoga on the lawn, movies under the stars and much more.brbrThe town of Greenport is less than a 5 minute drive. Greenport has many restaurants, shops and activities. Being on Long Islands north folk you only minutes away from the wineries.

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Bath

Sleeps

$1747.25

/ Nightly

Private Vacation Home

Greenport Villa with a Pool

Greenport, New York, United States

Bring the whole family to this great place with lots of room for indoor and outdoor activities! brbrEnjoy an entire Greenport home to yourselves. You have access to all rooms on the first and second floors, an enclosed back yard with a partially covered deck, large patio, in-ground pool, and back yard.

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Bath

Sleeps

Exceptional(75)

$856.88

/ Nightly

Private Vacation Home

Antique house, Private & Peaceful Oasis

Greenport, New York, United States

Newly restored antique home, 3 bedrooms, 1.5 baths with outdoor shower surrounded by manicured lawn & bucolic grounds. brSunlit and immaculate, decorated in a simple seaside style. brThree cozy, fresh bedrooms with full closets. br1.5 Baths with all new luxe fittings and finishes. brOutdoor spa shower (after May 1). brProperty backs onto protected wetland/ wildlife sanctuary. brProperty not suitable for children. brCentral air conditioning. brCentral heat. brOff-street private parking for 3 cars max. brHi-speed internet/ WiFi. brSmart 43” TV in living room. brBose bluetooth speaker.brNightstand charging stations in all bedrooms. brLarge outdoor side deck with Adirondack chairs/ tables. brGas 3 burner grill. brScreened-in all season front porch. brCustom kitchen with all new appliances. brStocked with glass/ table/ cookware, coffee pods, teas & spices. brDeluxe toiletries and hair dryer provided. brCompletely new laundry room. brOn The North Fork’s renowned Wine Trail and close to craft breweries.brWalk or bring your bike and ride to downtown Greenport and Sound or Bay beaches.brbr“Come to our enchanted getaway and . . . just breathe”

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Bath

Sleeps

Exceptional(7)

$875.67

/ Nightly

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.

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Bath

Sleeps

Exceptional(6)

$473.33

/ Nightly

Private Vacation Home

Newly Renovated - Walk to Town and Beach

Greenport, New York, United States

Brand new gut renovation - 3br, 3 full bath unit in the heart of Greenport Village! Have it all - walk to the train and Jitney, town, beach, Shelter Island ferry and more! This second floor unit features large windows and great natural light, central air, in unit washer and dryer, en suite bathrooms for each bedroom, all brand new. Fenced in, tree covered back yard when you need to escape the sun. Have all that the North Fork has to offer right outside your doorstep!

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Sleeps

$1550.72

/ Nightly

Private Vacation Home

Casa Greenport Top Floor

Greenport, New York, United States

Come enjoy all Casa Greenport top floor has to offer! Just one block from main street walk to several restaurants, shops, and the waterfront. 15 min walk from the Greenport train and Jitney Stop. You'll have plenty of private space with 3 bedrooms, 2 baths, a spacious living room and outdoor deck or lounge by the shared pool and make some friends.

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Bath

Sleeps

Exceptional(4)

$776.9

/ Nightly

Private Vacation Home

The Oyster House: An artful home nestled in the village of Greenport

Greenport, New York, United States

brA much-loved home welcomes you along with all of the wonders that Greenport has to offer. Within a two block radius you can be feasting on world-class Japanese, French, or one of the amazing raw bars.brbrThe house is situated a jaunty 10 minutes walk from two gorgeous beaches.brbrThroughout you’ll feel how much care has been invested here - be it the Turkish linens or the restorative new mattresses. Art books, novels, and a projector with all streaming services help to fill an ideal summer. brbrThe master bedroom provides a feeling of serene luxury, while the second bedroom charms equally. The third bedroom has double bunks - perfect for kids or teens or just anyone with a sense of nostalgia and fun.brbrYou will wake up to birdsong. brbrEnjoy the garden, which features a deck with seating for 8, a new grill, a fire pit, and a hammock.brbrThe kitchen is fully equipped and ready for your brilliance, with a functional gas fireplace and a dining table for 8.brbrMany New Yorkers will be thrilled to know there’s no need for cars, the house is a five minute walk from the train station and the Jitney. It’s a walking village.brbrThe Oyster House is much like its namesake, it’s a treat.brbrContact me for longer Summer stays.

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Bath

Sleeps

Exceptional(12)

$821.67

/ Nightly

Private Vacation Home

Relaxation in Greenport

Greenport, New York, United States

Renovated house located in the heart of Greenport is perfect for family getaways. Blocks away from Main Street. With amazing restaurants and bars in town, and 3 min drive to the beach. Book your stays with us in Greenport New York.brThere are 3 bedrooms on the second floor; a roomy master suite that includes a separate sitting area with a large 55 flat screen smart TV. All bedrooms are equipped with ceiling fans for those breezy summer nights. Full size bathroom are located on each floor. First floor living room is equipped with a 65 smart TV and pull out queen size Tempur-pedic sofa. brCentral air is installed throughout the home and controlled by Smart thermostats. Full size kitchen has all the cooking and baking necessity needed for a cook out. With Sub-Zero refrigerator, Wolf range gas stove, Bosch dishwasher and stainless steel farm sink, this will make cleaning and entertaining a joy. Off the kitchen and through the large sliding doors you'll find all your outdoor grilling needs. Our spacious fenced in grassy yard is where you'll find our relaxing and restful outdoor furniture. brbrHampton Jitney Greenport, Long Island Railroad and the Shelter Island ferry are all conveniently located 2 blocks away.

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Sleeps

Exceptional(6)

$1096.8

/ Nightly

Private Vacation Home

Greenport Village walking distance to all

Greenport, New York, United States

3 bedroom 2 floor cape with large great room and enclosed patio perfect for families and small groups. Relax in the hot tub after exploring the best wineries Long Island has to offer. Less than one mile to the heart of Greenport's shopping district. Explore the restaurants, shops, carousel and ferries. Minutes to the beach. Large kitchen if you prefer to stay in and enjoy the local wine you just picked up.

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Sleeps

$1224.76

/ Nightly

Private Vacation Home

Relax in this light-filled home, steps from the beach and a short walk to town!

Greenport, New York, United States

The perfect getaway. Within walking distance to beach, town, Jitney, LIRR and ferries to the South Fork. This quiet and bright house is located in the heart of Greenport. Enjoy wineries, breweries, amazing restaurants, shops and beaches.brbrGuests have the entire house, 3 bedrooms, 2 full bathrooms, fenced in outdoor space with all the amenities: outdoor shower, Weber grill, yoga shed, fire pit, hammock, Nespresso machine, board games, karaoke mic, etc... There is also a fully-equipped gym in the basement with treadmill, stationary bike, and weights.

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Bath

Sleeps

Exceptional(1)

$1697.14

/ Nightly

Private Vacation Home

Luxury Greenport Retreat - 5 min walk to Private Beach & Heated Saltwater Pool

Greenport, New York, United States

Welcome to The Cove NoFo, a light-filled, family friendly escape in Greenport just steps to your private beach. This 4-bedroom home is perfect for families or groups. Spend lazy afternoons by the pool, wander Greenport’s shops and restaurants, and end the day watching the sunset on the beach with a glass of wine from nearby vineyards.brbrFour bedrooms can comfortably sleep 6-8 adults and 2+ children. The kids bedroom features a twin bunk bed and trundle mattress. Two pack n plays available upon request.brbrFollow us @thecovenofo for more photos and our favorite places in the area.

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Bath

Sleeps

$2586.81

/ Nightly

Private Vacation Home

Casa Greenport

Greenport, New York, United States

Come enjoy all Casa Greenport has to offer! Just one block from main street walk to several restaurants, shops, and the waterfront. 15 min walk from the Greenport train and Jitney Stop. You'll have plenty of space with 6 beds, 3 baths, 2 kitchens, 2 living rooms, outdoor dining area, outdoor deck, and pool.

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Bath

Sleeps

Exceptional(11)

$1383.54

/ Nightly

Private Vacation Home

Beachfront Greenport Villa

Greenport, New York, United States

Stunning 3BR/2.5BA beachfront retreat in Greenport, directly on the Long Island Sound. Enjoy breathtaking water views, direct beach access, and a beautifully renovated interior. This light-filled home comfortably fits your group and offers a dedicated workspace, fireplace, and outdoor fire pit. Walk to local restaurants or bike to wineries. Your perfect North Fork getaway awaits!brStep inside this beautifully renovated beach house, where large windows flood the space with bright, natural light, creating a wonderfully airy atmosphere. The home features three comfortable bedrooms and 2.5 modern bathrooms, providing ample space for your group to relax.brbrThe main living area invites you to unwind, perhaps with a movie on the TV or by the warmth of the indoor fireplace on a cool evening. For those who need to plug in, a dedicated workspace and reliable Wi-Fi are also available. Your favorite spot may be the enclosed porch or the back deck, both perfect for taking in those magnificent beach views.brbrKey Features:br* Three comfortable bedroomsbr* 2.5 modern bathroomsbr* Spacious living area with TVbr* Cozy indoor fireplacebr* Dedicated workspace with reliable Wi-Fibr* Enclosed porch and back deck with water views

Sleeps

Exceptional(7)

$528.41

/ Nightly

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.

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Bath

Sleeps

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!

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Rent a place that suits your needs

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Bath

Sleeps

Vacation Home Rentals By Owner In Greenport, NY

$1222.47

$598.67

$655.8

$1100.16

$1154.31

$750.93

$1747.25

$856.88

$875.67

$473.33

$1550.72

$776.9

$821.67

$1096.8

$1224.76

$1697.14

$2586.81

$1383.54

$528.41

$1079.69

Rent a place that suits your needs

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