Vacation Rentals By Owner In Greenport, NY

$1241.52

Cozy Greenport village cottage

Greenport, New York, United States

Family friendly cottage, nestled in a quiet street in Greenport village. The private property has fully fenced backyard, 4 bedrooms, 4 bathrooms, wood burning fireplace, fully stocked kitchen, outdoor seating, and gas grill. The property is in a double lot with a pool and a pool-house on the second lot, secluded from the listed home. The pool/pool-house are not part of the rental.brbrThe bedroom descriptions are as follows:brbrMaster bedroom is downstairs with a king bed and an ensuite. brIn addition to a fully stocked kitchen, dining and laundry area, the downstairs also has a living room with another bathroom, TV, two sofas and access to a serene, private patio. The dining area has a wood burning stove for winter nights that warms up the dining space. brbrThere are three bedrooms upstairs with two queen beds in two rooms and a set of bunk bed (a queen and a full bed) in the third bedroom. One of the queen bedrooms have an ensuite. The other two rooms share one large full bathroom. brbrThere are two sets of stairs from downstairs to access the bedrooms upstairs. brbrThere is also an outside patio in our backyard with a bbq and patio with dining area. Plenty of greenery in our backyard provides for room for kids to play while dinner is prepared and enjoyed outdoors.brbrThe house is situated in one of a double lot property. The two lots are separated by fence and lush garden with plenty of privacy. The house is in the larger of the two lots (nearly half an acre) with a gated entrance and driveway for two cars. There is also on street parking by the fence of the property. Guests have access to everything on this one lot.brbrWe provide all linens and towels. We do not have any beach chairs and do not suggest that our towels are taken to the beach. Please bring your own beach towels, if desired. If cleaning the towels at the house, please shake sands off them outside the house so laundry machine is not damaged due to the sand.

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$824.23

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Cottage

Greenport Waterfront Private Dock

Greenport, New York, United States

GREENPORT CONKLING PT CREEKFRONT MINT 3BR COTTAGE W/PRIME VIEWS - This cottage on a half-acre lot fronts on the pristine creek inside Conkling Point with one of the finest estuarine views in the Peconic Bay system. Facing southwest, it is bathed in soft light and summer breezes. The cottage was totally rebuilt for year-round use by one of the area's premiere restoration specialists between 1989 - 96 and update in 2016. On the first floor is a living room with two glass walls facing the creek and a see-thru fireplace to a dining room with sliding glass doors to the waterfront gardens. There is a nice country kitchen, 2-1/2 baths, 3 bedrooms (sleeps 8) and a shower bath with laundry. There is a first floor master bedroom with private bath and connecting screened-in porch with fine water views that are also enjoyed from bed. On the second floor are two bedrooms and a half bath. There is a dock and an attached two-car garage. The creek offers access to Southold Bay for shallow draft boats and an exceptionally safe and tranquil opportunity for kids to learn about fishing and boating. And for swimming, the property comes with rights to 200' of private beach on Peconic Bay.

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$553.32

/ Nightly

Condo

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Greenport, New York, United States

Waterfront Water's Edge luxury suite, Suite C-204 accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. brbrThe property is owned and operated by Tocaro Realty LLC. since 2007.brbrTHE SPACEbrAs the owners of Suite C-204, my wife and I take pride in welcoming you to our personal getaway retreat, which is truly la crème de la crème within the preferred Water's Edge category offering you one of the best all season panoramic waterfront views in the entire complex.brbrThe resort is well maintained and feels like it is brand new. Each of the 68 condominium suites are individually owned, decorated and maintained. Similar units my not be similar at all.brbrOur Water’s Edge suite is in the waterfront Captain's Roost Building on the second floor. The unobstructed views of the Long Island Sound and Connecticut from the master bedroom and its balcony as well as from the living room and its separate private covered deck are breathtaking. The stairs to the beach are located just yards away from the suite’s rear stairway. At approximately twenty feet above sea level, the bluff is just the right height to offer both fabulous panoramic views and access to the beach below.brbrThe master bedroom has two sliding glass doors, one leading to a balcony and one leading to the private covered deck. Only a limited number of units have a master bedroom with two screened sliding glass doors that let the light and sea breeze pour in and a balcony that faces the water. If you love romantic sunsets, the balcony off of the master bedroom offers one of the best all season waterfront views to the west in the entire resort.brbrSuite C-204 is in the Captain's Roost Building and offers a panoramic view that feels surprisingly secluded. The feeling of romance and privacy is enhanced by the separation of the Captain's Roost from the reception building, pool area and the other waterfront building.brbrThe master bedroom has a queen sized bed. The second bedroom has two extra length twin beds. The couch has a pull out full sized bed.brbrAlthough the unit can theoretically sleep 6 people, think carefully if you are considering six adults for more than a long weekend. The indoor and outdoor dining tables accommodate 4 people each. Make your own decision as to whether the space is adequate for six based on how you intend to use it and the personalities in your party. For some groups that is part of the fun, for others, not so much.brbrGUEST ACCESSbrFull access to condominium property, private beach, pool (through Labor Day), and coin operated washers and dryers in the basement ($1.00 per machine cycle, bring quarters).brbrbrTHE NEIGHBORHOODbrSee the North Fork Promotional Council's or other websites for things to do on the North Fork.brbrWater, waves, wineries, shopping, auto racing, fishing, boating, swimming, restaurants, antiques, golfing, etc. is all here on Long Island’s North Fork for your enjoyment.brbrSome people prefer the rural North Fork of Long Island during the spring and fall seasons. Don't miss the strawberry festival in the spring and pick your own pumpkins and apples in the fall before attempting to navigate a corn maze.brbrGETTING AROUNDbrSuffolk County Transit - local busbrHampton Jitney - long distance bus, more frequent service than the LIRRbrLong Island Rail Road - trainbrtaxi servicebrbike rentalsbrride share services such as Uber or Lyft are scarce, if available at allbrbrLOCATIONbrSome websites beyond my control describe the property being in the city center. The property is approximately 2 miles from downtown Greenport Village. While the terrain is relatively level making for a leisurely bike ride, it is a fairly long walk, so I strongly advise you to look at the map and make your own assessment of the property's location.brbrOTHER THINGS TO NOTEbrThe resort condominium has quite times beginning at 9:00 pm to 8 am. Call the resort's managing agent using the after hours emergency option if loud guests are an issue.brbr

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$963.18

/ Nightly

Private Vacation Home

Northfork Townhouse walk to all

Greenport, New York, United States

Discover the North Fork from our beautifully renovated 100-year-old townhouse! This charming home comfortably fits groups and is perfectly located within walking distance to town, beaches, restaurants, and a local brewery. Enjoy modern comforts like central AC, a new kitchen, and a private backyard patio with a grill. Your ideal getaway for exploring local wineries and coastal life.brStep into a freshly renovated, open-concept living space designed for comfort and relaxation. The home features central air conditioning to keep you cool during your stay.brbrThe main floor includes:br- A brand-new, fully equipped kitchen with modern appliances.br- A dining area that flows seamlessly from the kitchen.br- A cozy den with a pullout queen bed and direct access to the back patio.brbrSleeping arrangements are designed to comfortably accommodate your group:br- Master Bedroom: One king-sized bed.br- Adjoining Room: A small room connected to the master, featuring one twin bed.br- Second Bedroom: One full-sized bed.br- Den: One pullout queen-sized sofa bed.brbrThe townhouse offers a spacious, fully updated bathroom with a tub and shower, plus a convenient half-bath located just off the kitchen.

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$799.75

/ Nightly

Private Vacation Home

Renovated Townhouse walk to all

Greenport, New York, United States

Discover the North Fork from our stylishly renovated 100-year-old townhouse! Perfectly located, you can walk to town, beaches, and a local brewery. This bright, airy home features a new kitchen, central AC, and a private patio with a grill. Comfortably sleeping up to 8 guests, it's the ideal base for families or groups exploring Long Island's wine country. Park your car and enjoy a walkable getaway!brOriginally built over 100 years ago, this home has been completely updated to offer a bright, airy, and stylish retreat. The open-plan main floor features a comfortable living area with a wall-mounted TV, a spacious dining room, and a brand-new, fully equipped kitchen, creating a seamless flow perfect for relaxing and entertaining. The space is filled with natural light and boasts all-new appliances and central AC for your comfort.brbrThe modern kitchen is equipped with stainless steel appliances and opens directly to the dining room and a cozy den, which provides access to the back patio.brbr**Sleeping Arrangements:**br* Master Bedroom: A very spacious room with a comfortable King-sized bed.br* Second Bedroom: A small room, located just off the master, with bunk beds.br* Third Bedroom: Features two Twin beds, one of which is a convenient Murphy bed.br* Den: Includes a Queen-sized pullout bed for additional guests.brbr**Bathrooms:**br* A spacious full bathroom with a tub and shower.br* A stylish half-bathroom is conveniently located off the kitchen.

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$331.83

/ Nightly

Apartment

NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants

Greenport, New York, United States

PLEASE READbrbrPlease park in the street when arriving as many spots along the streets are available.brbrLaundry + Dryer is only available for reservations over 7 days (1 week).brbrNewly Renovated 2BR Apartment House - 1st FloorbrPrivate Entrance - Full Apartment HousebrbrNo petsbrNo shared spacebrSeparate entrancebrClose to wineries and transportation S92 bus, Hampton Jitney, Long Island/North Fork/Connecticut Ferries, restaurant and beaches!brbrCheck-in is anytime after 3PMbrCheck-out at 11AMbrbrSingle Apartment Includes 2 Bedrooms, Living Room, Kitchen and 1 Bathroom - WiFi and Cable is also Included as well as a 42+ TV - Fully Renovated at Jun 2016 - Walk-able to Restaurants, Bars, Beaches, and more - Close-by to Ferries - Duplex - Apartments are very family-friendly and fully furnished - Owners are very friendly - Beaches are nice - Weddings, Couples, Family Vacations packages are available

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$714.07

/ Nightly

Cottage

Rose Cottage by the Bay.

Greenport, New York, United States

Seaside Greenport Village HistoricbrDistrict, on Long Island’s North Fork, New York.brbr“Rose Cottage” is within the Greenport Village Historic District with water views of Sterling Harbour’s busy mooring field of classic to modern sailboats, and power. Fish as close as the Village dingy dock, two doors away: rent a boat, or slip, or launch your own, within a local clam’s throw. Bathe in and eat from some of Long Island’s (or the world’s) most pristine water quality maritime environments.brbrGreenport Village is the gem of Long Island’s few active seaside villages: off the beaten path yet easily accessible from New York City by the LIRR, Hampton Jitney or car, or from Boston by car or Amtrak and the New London-Orient Ferry. br brRose Cottage is an easy stroll from the Village Center and its restaurants, cafes, boutiques, gourmet shops, many art galleries and antique shops, banks (ATMs), bookstore, hardware and marine supplies, farm stand and supermarket.brbrGreenport Eating is a pleasure from picnics at the many beaches, or harbour front Mitchell Park, with its Carousel and live entertainment, to waterfront clam bars, diner, cheese emporium, and tea shop, and of course more formal fine dining with top chefs and local food.brbrDay Trips might include the quaint Orient Village, Sag Harbour, Orient Ferry roundtrip, the ‘Peconic Star’ to Block Island, Nature Conservancy's Mashomeck Preserves, Audobon Society’s birding and Town’s trails and woods, walk on the Shelter Island Ferry and stroll among the gingerbread houses and restaurants of the ‘Heights’.br brGreenport village is in the heart of the award winning North Shore Wine Country, with tasting rooms and live entertainment.brbrGreen Farm Stands all the time and Saturday morning tag sales and flea markets.br brAll surrounded by the sea.br br“Rose Cottage” is beautifully furnished and styled by its owner, the former decorating editor of a national magazine, with an open floor plan, spacious rooms, gourmet kitchen: very light, and very airy. br brA two story Cape, two bedrooms (one queen, one double) and full bath upstairs, main floor master bedroom/front parlor with queen sofa couch and full bath (sleeps 4) kitchen dining room with half bath, large sun filled living room, couch sized reading bay window, and fireplace for cozy fall and winter evenings, “Rose Cottage” is surrounded by beautiful gardens, ideal for outdoor entertainment, fountains, mini ponds, and a pergola.br brOther amenities include washer/dryer, dishwasher, central air and heat, fireplace, cable TVs, internet access, personal chef available for shopping, cooking, small dinner parties, lunches, picnics. brbrbrbrKeywords: Cottage, Water Views, Walking Distance to Town and Public Transportation

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$856.88

/ Nightly

Private Vacation Home

Overlook a Vineyard, Walk to the Beach, and only a Short Walk to Town - 5 Star!

Greenport, New York, United States

Discounts available for stays 14 days. Please inquire prior to booking for details.brbrCompletely updated, modern and light-filled Cape Cod-style home. You cannot beat this location overlooking the vineyard and only a short walk to the beach or a short stroll to town. The home is beautifully decorated and professionally maintained to ensure an exceptional experience every time. Check out what our guests had to say - every one of our reviews are 5-star!brbrLONG TERM RENTAL RATES:br- Summer season (Memorial - Labor Day): $18,000br- 30 day stays: 50% rate discountbr brThe town zoning law requires that property be offered for rent for a period of no less than 14 nights. During this time period, you will have the exclusive right to occupy the property, but you may not sublet the property. No guests are allowed to be on the property unless you are also occupying the property. Please inquire if you have any questions @ 646-245-4576.brbrEnjoy dining alfresco on this beautifully landscaped 0.25 acre property overlooking the sprawling Kontakosta Vineyard; outdoor space includes a fire pit, gas and charcoal grills, and a dining table for 8. This peaceful retreat offers visitors the best that Greenport has to offer: take a quick 15 minute walk to town for dining and shopping, stroll around the corner for a waterfront wine tasting or visit the famous “67 Steps” beach located at the end of the street.brbrInside the home, relax in an open concept kitchen and dining space that includes a large chef’s kitchen with every cooking amenity you need; dishwasher, microwave, gas range and washer / dryer. The dining room has a cathedral ceiling and seats 8. The living room has a working wood burning fireplace, flat screen Smart TV, and WiFi. brbrA cozy screened porch with ceiling fan and lounge seating offers a peaceful spot perfect for morning coffee or catching up on a good book. brbrThe master bedroom with king-sized bed and bathroom are on the first floor. The second floor features two bedrooms with a king and full size bed, respectively, a sleeping alcove and bathroom with large glass shower. brbrLiving and sleeping spaces on the first and second floor have ceiling fans; window A/C units are also available from Memorial Day through Labor Day. Linens and towels included. brbrBedroom 1: KingbrBedroom 2: KingbrBedroom 3: Fullbr+ alcovebrSleeps 6brbrThe home is not ideal for toddlers and small children. brbrNo pets.

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$747.19

/ Nightly

Private Vacation Home

Entire, new, roomy, village beach house close to beach, park, and town center

Greenport, New York, United States

Welcome to our most lovely Greenport Beach Home.....800 feet to sixth street beach and playground. A true beach getaway, with beautiful outdoor patio, outdoor shower, covered front porch and covered balcony off the master bedroom. Spacious private yard, cruiser bicycles to explore this quaint, bustling, historic North Fork town....Walk to main street restaurants, Shoppes, waterfront, lively bars, taverns, and our acclaimed carousel, park. your vacation will make lasting memories.......

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$564.03

/ Nightly

Condo

Sensational, newly remodeled waterfront Greenport condo

Greenport, New York, United States

A beautiful waterfront condo just a short walk from historic Greenport village, this newly remodeled unit provides stunning waterfront views, two modern bathrooms, a renovated kitchen, a dedicated boat slip, and community tennis/pickleball courts, an award-winning swimming pool on the Peconic Bay, and is located close to all the wineries, farm stands and beaches the North Fork has to offer. With four comfortable bunk beds in one bedroom and a new queen-sized bed in the master, your whole family will love staying here. Note: Inquire about renting our additional unit located right next door and enjoy extra accommodations for friends and family. brbrWe are not allowing pets; however, if you have a small pet (under 10 lbs.) there will be an additional fee of $35 p/night.brbrAlso, if A/C is used, there will be a fee of $100 for the entire stay.brbrAdditional guests (more than two adults) will be charged an additional fee of $100 p/guest p/night.

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$471.28

/ Nightly

Private Vacation Home

4BR Cape Home w Lg Screened Porch. 1m walk/drive Greenport Shops + Dining.

Greenport, New York, United States

Renovated cape-style home with central ACbr- Living room w55 Smart TV + sound systembr- Sunny, large den with w65 Smart TV + sound systembr- Open indoor dining area off full kitchenbr- Large, screened porch with comfortable seating + additional outdoor dining table + kitchen efficiency cabinets with a sink and kitchen pass-through windowbr- 4 bedrooms: white bed linens included. (1st Fl: Double + 1st Fl: Twin + 2nd Fl: Queen + 2nd Fl: Queen with Twin Beds)br- 2 bathrooms: white towels included. (1st Fl: Full Bath w/Tub-Shower + 2nd Fl: Full Bath w/Large Shower)br- Wi-Fi includedbr- Weekly cleaning service includedbr- 30+ Day 5.5% discount to offset local tax feesbr- Manicured lawns and seasonal gardens for outdoor enjoymentbrbrClose to Greenport Village shops and restaurants (1 mile). Close to several North Fork beaches (1/2+ mile).

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$699.1

/ Nightly

Private Vacation Home

Walk to Beach and Greenport Village, Two King Beds

Greenport, New York, United States

A quiet Cape home within walking distance to all Greenport Village has to offer - dining, shopping, the beach and transportation hub. A perfect getaway for families, couples or friends who want to explore the North Fork, including wineries, breweries and boating. You’ll be glad you stayed at Doc Out East! Newly finished full bathroom and kitchen, and two king size beds. Large fenced back yard, private furnished deck with gas fire pit, grill and yard games. Walking distance to town beach, village of Greenport and the transportation hub. Ring Doorbell Cameras on Exterior Doors. In order to abide by local policies, we will block 14 days on our calendar for each stay.br

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$2149.61

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Private Vacation Home

Modern Farmhouse Private Estate, 6.5 acres

Greenport, New York, United States

Welcome to your private 6.5 acre getaway. With 4 bedrooms and 6 bathrooms, this spacious and beautifully designed home is perfect for families or couples seeking a luxurious getaway, mixing the privacy and tranquility of unobstructed farmland and the perfect location - 2 minutes from bay and sound beaches, 5 minutes from Southold and Greenport towns, farmstands and vineyards!brbrThe first floor features an open layout, with a chefs kitchen, dining room table with seating for 12 and a panoramic view of a lush 4 acre meadow. It also features a formal sitting room and cozy media room with a 70 TV and plenty of toys for all children 5 and under, 2 half bathrooms and one full bathroom, ensuring that all guests have ample space and privacy.brbrThe second floor boasts a magnificent master bedroom with an ensuite bathroom and a private terrace that overlooks the vast private field. Guests can also enjoy a queen bedroom with an ensuite bathroom, a king-size bedroom with a terrace , and a 4th bedroom that can be configured with 2 cribs or 2 twin beds, depending on your needs.brbrOur home has been designed to let in plenty of natural light, and the southern exposure means that every room is bathed in sunshine throughout the day, whether you're inside relaxing or tanning by the 40x20 gunite pool, complete with loungers and umbrellas.brbrThere's plenty of space to lounge, dine, and socialize on our spacious pool deck, which is equipped with comfortable furniture and a barbecue.brbrLocated in the heart of Greenport, our home is just a stone's throw from some of the town's best attractions, including restaurants, bars, and shops. Whether you're looking to explore the local area or simply unwind in style, our rental home is the perfect choice for your next vacation.

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$389.46

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Apartment

Charming Greenport Gem 1, 1 Mile to Ferry!

Greenport, New York, United States

Travel to the North Fork of Long Island for a much-needed getaway and experience both modern luxury and historic desire at this 2-bedroom, 1-bathroom vacation rental! Situated in the heart of Greenport, this apartment provides an updated interior, historic feel, a fully equipped kitchen, and a walkable location near town attractions. Take the ferry to Shelter Island and enjoy a day on Shell Beach. Explore Orient Beach State Park and grab a glass of wine at a vineyard on the way back.br-- THE PROPERTY --br2nd-Floor Apartment in Historic Home | Walk to Downtown Boutiques & Restaurants | Near Beaches brBedroom 1: Queen Bed | Bedroom 2: Full Bed | Living Room: Queen Sleeper Sofa | Additional Sleeping: Pack ‘n PlaybrAPARTMENT FEATURES: 3 flat-screen TVs w/ cable, dining table, laptop-friendly workspace, gardenKITCHEN: Stainless steel appliances, dishwasher, cooking basics & spices, Keurig coffee maker, blender, toaster, tea kettle knife set, dishware & flatwareGENERAL: Free WiFi, central A/C, linens & towels, central heating, complimentary toiletries, trash bags & paper towels, hair dryer, hangers, self check-inFAQ: Ring Doorbell device (facing front door entry), quiet hours (10:00 PM-8:00 AM), no porch access, addt'l rental on-site (separate unit & entrance)ACCESSIBILITY: Stairs required for access, entire 2nd-floor unitPARKING: Street parking (first-come, first-served), no driveway parkingADDT’L ACCOMMODATIONS: An additional 1-bedroom property for 4 guests is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbr-- THE LOCATION --brTHINGS TO SEE + DO: Antique Carousel (0.4 miles), East End Seaport Museum & Marine Foundation (0.7 miles), The Fire Fighter (0.7 miles), Ferry to Shelter Island (0.7 miles), Railroad Museum of Long Island (0.7 miles), Horton Point Lighthouse Nautical Museum (5.5 miles)OUTDOOR RECREATION: 67 Steps Beach (1.1 miles), Norman E. Klipp Marine Park (1.8 miles), Crescent Beach (2.7 miles, accessible by ferry), Truman’s Beach (4.0 miles), Mashomack Preserve (6.4 miles, accessible by ferry), Shell Beach (6.4 miles, accessible by ferry), Orient Beach State Park (10.4 miles)WINERIES + BREWERIES: Greenport Harbor Brewing Company (0.3 miles), One Woman Winery Greenport (0.4 miles), Kontokosta Winery (1.2 miles), The Old Field Vineyards (4.0 miles)AIRPORTS: Long Island Islip MacArthur Airport (44.0 miles), Laguardia Airport (90.9 miles), John F. Kennedy International Airport (91.9 miles)br-- REST EASY WITH US --brEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.br-- POLICIES --br- No smoking - No pets allowed- No events, parties or large gatherings- Additional fees and taxes may apply- Photo ID may be required upon check-in- NOTE: This apartment is an entire 2nd-floor unit of the building and requires stairs to access- NOTE: There is an additional rental unit on-site with a completely separate entrance - NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed- NOTE: Please observe quiet hours between 10:00 PM to 8:00 AM- NOTE: The porch is not available for guest use

2

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1

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6

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$1414.53

/ Nightly

Lodge

Beach lodge with private beach-2.5 acres of quiet nature,4 beds, chef’s kitchen

Greenport, New York, United States

Your cozy East End retreat awaits in Greenport, NY at this fabulous lodge with a private beach. Sleeps 11 : four bedrooms featuring a king bed, two full beds, two twin beds, and a sofa bed, there’s plenty of space for guests to relax comfortably in two living rooms, full dining & large chef’s kitchen with Viking appliances. Four bathrooms include showers and bathtubs, making it easy for everyone to refresh after a day of adventure on the beach or in the beautiful coastal town of Greenport ( a short 5 minute drive) packed with restaurants, cafés, cocktail bars, farmer’s markets and home to Greenport brewery. The lodge stays comfortable year-round with heating and air conditioning. Whether you’re gathering in the spacious living areas or unwinding in the tranquil bedrooms, this nice lodge offers a perfect getaway to recharge & relax. This large 2.5 acre property has beautiful park like trees & two outdoor decks. Book now and enjoy everything this lodge has to offer.

4

Bed

4

Bath

11

Sleeps

$386.06

/ Nightly

Apartment

2-Bedroom in Village of Greenport with Backyard

Greenport, New York, United States

This phenomenal rental in Greenport offers a cozy retreat for guests. Walk to the best the village has to offer right from the rental. With 2 bedrooms, heating, WiFi, and a washing machine, this cool space has everything you need for a comfortable stay. Relax in the inviting atmosphere and soak in the charm of Greenport during your visit. Enjoy the backyard patio and grill on a summer night. Come and experience the magic of Greenport at our rental.

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$306.57

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Cottage

Peaceful, clean cottage, 10 min walk to town. Monthly rates. Fenced backyard

Greenport, New York, United States

We welcome you to our cottage away from it all but still close to all activities that make the North Fork a magical place to visit. Within 5 - 15 minutes you can walk to all that the Greenport town has to offer and to 2 beaches. No need to have a car as you can walk from the train or bus from the city. Our fenced in back yard is perfect for dogs and little humans to roam freely and has a basketball hoop, dining table, metal firepit and lounge space.. The cottage is simple, clean and cozy, a real home full of character and charm, with a fully stocked kitchen, screened in front porch, and large flat screen TV with Xbox. Sheets and towels are high end and mattress is new for maximal comfort. Our home is perfect for those seeking peaceful relaxation yet close to terrific restaurants, farms and wineries. Beach chairs and basic beach bikes also available on request so you really can pack minimally. Beach pass obtainable for long term renters.brbrPlease note - local law requires 14 night stay for home rentals. While we offer significant discounts to enable you to stay longer, we will adhere to this law by blocking dates after shorter term stays. Rental permit ID 965.

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$1085.38

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Private Vacation Home

SUMMER RETREAT: Beach, Dock & Pool overlooking the Peconic Bay in Greenport!

Greenport, New York, United States

Welcome to Gull Harbor!brbrNew gunite pool, Summer 2025! See renderings, will provide photos upon completion.brbrThe house size is deceiving. It is great for multiple families as part of it is a guest en suite. Updated kitchen and perfect dining area, deck with a beautiful view and on an acre plus of land. Gull Harbor has an upstate feel and charm, located on the quaint North Fork a mile and a half from town.brbrBring your boat as the property has a deep water dock and 380' of bulkhead. It is adjacent to a town beach. Lazy summer afternoons. Fish, clams, crabs and oysters are abundant. brbrRecently added a playground for children with a bench seating area. Wood burning fire pit right on the edge of the bulkhead. Sit in Adirondack chairs and roast marshmallows with a salty, southern breeze.brbrVery close to vineyards, breweries and all of the culinary offerings the North Fork has to offer!

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$319.9

/ Nightly

Private Vacation Home

5 minute walk to beaches and beautiful downtown Greenport

Greenport, New York, United States

Lovely Victorian home with private entrance, porch, and brick patio. Floor to ceiling windows in light filled large bedroom with en suite bathroom. Cozy den has a beautiful bay window and a queen size pull out sofa bed for additional guests. Sunny sitting room just off of the kitchen for reading or games. Full kitchen, washer dryer, high speed internet, brand new flat screen TV can be found in the unit. The West Elm king size bed, mattress and sofa bed are all new.brNo car needed as the train station, fantastic restaurants, bars, shops and Shelter Island ferry are less than half a mile walk from the house.brEnjoy all that Greenport and the North Fork have to offer from this amazing location!

1

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1

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4

Sleeps

$566.62

/ Nightly

Private Vacation Home

Beachy Craftsman Cottage—Fire Pit, Music & Walkable Location

Greenport, New York, United States

Welcome to your perfect North Fork getaway in Greenport—a charming 1903 Craftsman cottage that blends historic character with modern comfort. Nestled in the heart of this vibrant seaside village, our home offers a relaxed, walkable escape where you can leave the car behind and fully unwind.brbrThis cozy three-bedroom, 1.5-bath home comfortably sleeps up to six guests and is thoughtfully designed for easy, breezy living. Enjoy central air-conditioning on warm summer days, and rinse off after the beach in the refreshing outdoor shower. Evenings are best spent gathered around the fire pit under the stars, sharing stories and making memories.brbrInside, the cottage invites you to slow down and savor the moment. With its warm, cozy vibe and artistic touches, it’s a perfect retreat for families, couples, or friends. Music lovers will feel especially at home—guests are welcome to enjoy the piano, guitar, and ukulele for a spontaneous jam session or a quiet evening of creativity.brbrWhether you're seeking a peaceful beach escape, a charming small-town experience, or a creative retreat, this one-of-a-kind cottage is ready to welcome you.brbrALLERGY FRIENDLY: I keep a gluten and soy free kitchen and can set aside separate cooking tools if you need. The kitchen is not nut-free, though I rarely use peanuts. There are very light rugs and curtains around the house to cut down on dust and pollen. Central air conditioning offers relief from seasonal allergies.brbrDOG FRIENDLY: There is a fenced dog run to keep your puppy safe and happy. My little one likes to sit in the sun, dig and zoomie!

2

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2

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3

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Vacation Rentals By Owner In Greenport, NY

$1241.52

$824.23

$553.32

$963.18

$799.75

$331.83

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