Vacation Rentals By Owner In Greenport, NY

The LocationbrbrSterling Harbor, the marina of Greenport, is the prime location in this sought-after area on the North Fork of Eastern Long Island, popular for its restaurants, boutiques, museums, maritime history, nestled among vineyards and surrounded by beaches.brbrThe AccommodationbrbrThe studio is situated in a large garden, which can, of course, be used for relaxing, barbecuing, or playing. The separate entrance leads into the very spacious (approx. 65 sq m) fully equipped and very comfortable living/sleeping area with a dining table, sofa, TV, bookshelf, refrigerator, wet bar, and four separate, self-contained beds. A sauna is also available.brbrSeveral cozy seating areas in the garden, some with harbor views, invite you to linger.brbrGreenportbrIt's just a short walk to a variety of sights and attractions in Greenport. Beaches, wineries, charter boats, and amusement parks are all within easy reach by car. The landlord/owner is German and will gladly arrange your transfers.brbrThe glittering village of Greenport is a 5-minute walk away. Enjoy Greenport's seaport by admiring the picturesque houses along the docks or in the historic districts. Be sure to visit the Seaport Museum, the Railroad Museum, the vintage Greenport Movie Theatre, the antique carousel, the fireboat, and our beautiful centuries-old public library.brbrRestaurants and shopping are just steps away. Greenport offers a variety of dining experiences, from casual to fine dining. You can find fresh seafood, wood-fired pizza, delicious Latin American, New American, pub-style, sushi, Mediterranean, and much more, all within walking distance. There are also tasting rooms for beer, wine, and tea, as well as cafes and restaurants specializing in breakfast and lunch. Visit the galleries, boutiques, and antique shops as you stroll to and from your restaurant, or charter a boat for sightseeing or fishing.brbrThe SurroundingsbrIf you'd like to explore beyond the village, you can take the ferry to Shelter Island (a beautiful 10-minute cruise). Orient State Park offers nature-filled hikes. The Long Island Railroad or the scheduled Hampton Jitney bus will take you to New York City for a day trip. Or, take the Long Island car ferry to New London and explore Connecticut, one of the original New England states.brbrLocation Details for the 2026 Soccer World Cup:brGreenport, located on the North Fork of Long Island, lies between New York City (2026 match venue: East Rutherford, NJ) and Boston (2026 match venue: Gillette Stadium), making both cities easily accessible.brbrEast Rutherford (MetLife Stadium) will host eight matches, including the 2026 World Cup Final (July 19), several group stage matches (Brazil vs. Morocco, France vs. Senegal, etc.), a Round of 32 match, and a Round of 16 match. Boston (Gillette Stadium) will host seven matches, including group stage matches (Haiti vs. Scotland, etc.) and a quarter-final.brbrbr``` East Rutherford (MetLife Stadium) - 8 matchesbrJune 13: Brazil vs. Morocco (Group Stage)brJune 16: France vs. Senegal (Group Stage)brJune 22: Norway vs. Senegal (Group Stage)brJune 25: Ecuador vs. Germany (Group Stage)brJune 27: Panama vs. England (Group Stage)brJune 30: Round of 32 MatchbrJuly 5: Round of 16 MatchbrJuly 19: The FinalbrBoston (Gillette Stadium) - 7 matchesbrJune 13: Haiti vs. Scotland (Group Stage)brJune 16: Norway vs. FIFA playoff winner 2 (Group Stage)brJune 19: Scotland vs. FIFA playoff winner 2 (Group Stage)brJune 23: England vs. FIFA playoff winner 1 (Group Stage)brJune 26: Norway vs. FIFA playoff winner 1 (Group Stage)brJune 29: Round of 32 matchesbrJuly 9: Quarter-Final Match

Apartment

Sterling Harbor, walking distance to the center: spacious studio for 4 people

Greenport, New York, United States

1

Bath

Sleeps

Exceptional(11)

$1383.54

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

Beachfront Greenport Villa

Greenport, New York, United States

8

Sleeps

Exceptional(7)

$528.41

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.

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

Greenport, New York, United States

Bed

Bath

Sleeps

$1079.69

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!

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

Greenport, New York, United States

Bed

Bath

Sleeps

$618.86

Three bedrooms, 2 bathrooms completely renovated home. Sleeps 6. New outdoor shower. Fully renovated. All bedding freshly washed and beds made, towels, 6 beach chairs and 6 plush beach towels are included. Washer and dryer on main floor. large air conditioned barn- also renovated- with refrigerator, television, ping pong table, dart board, WIFI, table and chairs and work station with charging outlets. One block from the center of Greenport Village. Two blocks from the waterfront park, carousel and great Greenport restaurants! Walk 9 blocks or drive to Fifth Street beach-no permit required. Bathrooms, playground. Orient State park is a 7 minute drive. Sandy beach, concession, bathrooms, kayaking. Short bike ride or car ride to vineyards, beautiful trails and other North Fork towns. Around the corner from the supermarket. Front porch with rocking chairs. Sip your morning coffee and enjoy! Front yard is fully fenced. Backyard is fully fenced as well. Sun drenched backyard has an outdoor fireplace ( great for roasting s’mores!) , new large brick patio new Weber barbecue, all new-table and chairs, chaise lounges and a bike rack. Add flavor to your food from our herb garden. Enjoy dining outdoors! Kitchen is equipped with unbreakable plates and glasses for outdoor dining . The renovated kitchen is fully stocked with pots, pans, gadgets and small appliances . The house has a new washer and dryer next to the kitchen and newly finished hardwood floors. There is WIFI, board games, playing cards and a fireplace. New appliances and granite counters in the kitchen and bathrooms.

Quiet street one block to shops, restaurants & waterfront. Barn with AC TV &WIFI

Greenport, New York, United States

Bed

Bath

Sleeps

$811.17

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

Bed

Bath

Sleeps

$885.44

Beautiful 2 bedroom 2 bathroom direct sound front condo in greenport at Cliffside resort direct view. heated pool, beach access, 5 min from town close to all local vineyards,farm stands and breweries that the north fork has to offer.

Condo

Beautiful Soundfront condominium

Greenport, New York, United States

Bed

Bath

Sleeps

$788.36

Be apart of the action in Greenport Village. Complete home, Lovely 3 bedroom (1 walk through), 2- and 1/2 bathrooms. 1846 Farmhouse. Completely renovated in 2023, all modern appliances and bathrooms. Central air. Gas stove. Combining the charm of an antique home with modern comfort. Quiet location in the historic district. Relaxing, fenced garden, with gas and coal bbq. A fire pit, and an array of lounging areas, with sun and shade available at all hours. Train, Jitney, Ferry, Restaurants, Shops and waterfront less than 1/2 mile.

Country House

Greenport Village Farmhouse.

Greenport, New York, United States

3

Bed

Bath

6

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

$685.5

Please Note : Guests must add a message with their reservation request, and kindly indicate who is traveling. brbrWelcome! The Captain’s Cottage is located in the seaport Village of Greenport on the North Fork of Long Island. George Graber was a Steamship Captain and the son of a renowned Schooner Smack Captain named William Anderson Graber. He grew up one street over on Fifth Street, and when he married his wife May Ellen Locker he moved in with her family to this cottage. More recently it was the home to the National SCRABBLE Association.br Just a few minutes’ walk from the restored 1880s home are the Shelter Island Ferry, the Hampton Jitney and the Long Island Railroad train station. When you arrive at this beautiful spot you won’t believe you are only 100 miles from midtown Manhattan. Within a few blocks of this cozy home you can be sunbathing at the Fifth Street Beach, fishing off the Railroad dock, playing with your children at the beach park or walking to town to sample one of the fine restaurants Greenport boasts. Why not try a tasting at the local Greenport Harbor Brewery or learn how to shuck your own oysters at the dockside Little Creek Oyster A comprehensive sampling of local menus will be provided at the cottage.br The 2-story cottage is at the corner of the Main Road and Fourth Streets, sleeps 6 and features three bedrooms: Queen, full and a room with two twin beds. There are 2 bathrooms, a full kitchen, dining room, living room and a small den-home office or game room. There is ample on-site parking and a screened porch for outdoor dining. This is a no-smoking property. The Cottage is just a few miles from Peconic Landing, so a convenient place to stay if visiting relatives there. Perfect for families. Sorry NO pets. No parties.br Property owners live 4 blocks away and will be happy to share information during your visit. Please note - the electronic calendar on this site does not necessarily reflect up-to-the-moment bookings. We request all interested guests to please email owner with information about your visit and who might be traveling with you. If accepted we will require the names of the guests, and ages if any are minors. br We look forward to hosting you.brbrGreenport Village Permit # R25-070

Cottage

Restored Seaport Village Cottage

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

$518.71

1896 Restored Victorian located within steps to a lovely Bay Beach. Village restaurants, shops, NYC Hampton Jitney Express Bus and Shelter Island Ferry are all within a short stroll. Fresh produce farms, vineyards, hills and fields surround this very special place to rejuvenate your spirit and have fun. Fishing off the pier, sun bathing, swimming and people watching are all available within a two minute walk. Orient State Park is within a few miles and also offers nature lovers breath taking views of birds and marshes as well as the Long Island Sound. Also in Orient is a Sea Jet Ferry available to those who may want to enjoy the Mohegan Sun Casino in Connecticut across the Long Island Sound or travel north.brbrPrivate and spacious accomodations for four adults include two bedrooms each with a separate living space and a fully equipped kitchen and bath decorated in a casual antique pine style. Our charming second floor apartment is peaceful, perfect for two couples or a family.brbr2021 HVAC upgrade includes UV /HEPA airflow filtration. Exterior security cameras offer added measure of safety during your stay.brbrbrTypical Day : Easy to rise in the morning and have a cup of coffee in the garden ..take a stroll down to the beach and people watch.. come back..get ready for the day..brbrLeave the 'House'.. walk left toward the village and turn right on Clark Street ..now take a three block walk to the village along fourth street and the bay..enjoy the many restored village homes and the simple life..brSo... are you ready to explore the village The antique Carousel on Front Street..antique shops..maybe a cup of stronger coffee at Aldo's...brStroll up and down Main Street..and Front Street and find your favorite shops/spots...Book, Toy, Cooking, Clothing......Art Galleries..Restaurants...Antiques...something for everyone.

Apartment

Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.

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

$1743.45

This brand new construction house is perfect for large groups. Gather with friends and family in the double height ceiling open concept living room/dining room/kitchen area. Soak up the sun lounging by the pool. Take a super short walk to town to enjoy the incredible local shops, restaurants, and bars. Then end with a nightcap relaxing in the hot tub. There's no better place to stay in Greenport Village.

Villa

New Construction Greenport Pool House - 3 Blocks from Town

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

$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

$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