Vacation Rentals By Owner In Greenport, NY

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

Cottage

Rose Cottage by the Bay.

Greenport, New York, United States

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Exceptional(16)

$719.16

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.......

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

Greenport, New York, United States

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Exceptional(5)

$357.75

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.

Condo

Sensational, newly remodeled waterfront Greenport condo

Greenport, New York, United States

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Exceptional(3)

$529.02

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).

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

Greenport, New York, United States

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Exceptional(2)

$630.55

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

Walk to Beach and Greenport Village, Two King Beds

Greenport, New York, United States

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Exceptional(6)

$418.92

Rental Permit 1063 Live the perfect life with a new Pied a Terre on the North Fork in Greenport. This lovely one bedroom apartment has everything you need for a getaway of any length. Well appointed furnishings, walking distance to the beach and village too. Your home has its own washer and dryer too! brExplore the Village of Greenport and the harbor and all of the North Fork wine country.brMinimum stays required as per Southold Town CodebrRental Permit 1063

Apartment

One bedroom Pied a Terre - a lovely new and clean Greenport place

Greenport, New York, United States

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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, indoor heating throughout the house, outdoor seating, fire pit 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.

Cottage

Cozy Greenport Getaway

Greenport, New York, United States

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This is a fully equipped home with an open floor plan kitchen and living room, a dining room, screened-in sunroom, a large saltwater pool with cabana, patio, gas grill and wood smoker. Pets are welcome to join you on this beach escape. A private community beach is available when you need a change from the pool or take a short drive into town for the many shops and restaurants that Greenport has to offer. We have lots of games if its your thing, bocce, croquet, and corn hole or just sit under our spacious umbrella and read a book. But don't forget to enjoy the outdoor shower afterwards and check out the local wineries.

Your Summer Escape

Greenport, New York, United States

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Exceptional(2)

$2418.54

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.

Modern Farmhouse Private Estate, 6.5 acres

Greenport, New York, United States

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Exceptional(16)

$307.24

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.brbr-- THE PROPERTY --brbr2nd-Floor Apartment in Historic Home | Walk to Downtown Boutiques & Restaurants | Near Beaches brbrBedroom 1: Queen Bed | Bedroom 2: Full Bed | Living Room: Queen Sleeper Sofa | Additional Sleeping: Pack ‘n PlaybrbrAPARTMENT FEATURES: 3 flat-screen TVs w/ cable, dining table, laptop-friendly workspace, gardenbrKITCHEN: Stainless steel appliances, dishwasher, cooking basics & spices, Keurig coffee maker, blender, toaster, tea kettle knife set, dishware & flatwarebrGENERAL: Free WiFi, central A/C, linens & towels, central heating, trash bags & paper towels, hair dryer, hangers, self check-inbrFAQ: Ring Doorbell device (facing front door entry), quiet hours (11:00 PM-8:00 AM), no porch access, addt'l rental on-site (separate unit & entrance)brACCESSIBILITY: Stairs required for access, entire 2nd-floor unitbrPARKING: Street parking (first-come, first-served), no driveway parkingbrADDT’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 bookingbrbr-- THE LOCATION --brbrTHINGS 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)brOUTDOOR 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)brWINERIES + 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)brAIRPORTS: Long Island Islip MacArthur Airport (44.0 miles), Laguardia Airport (90.9 miles), John F. Kennedy International Airport (91.9 miles)brbr-- REST EASY WITH US --brbrEvolve 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.brbr-- POLICIES --brbr- No smoking br- No pets allowedbr- No events, parties or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This apartment is an entire 2nd-floor unit of the building and requires stairs to accessbr- NOTE: There is an additional rental unit on-site with a completely separate entrance br- 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 pressedbr- NOTE: Please observe quiet hours between 11:00 PM to 8:00 AMbr- NOTE: The porch is not available for guest use

Apartment

Charming Greenport Gem 1, 1 Mile to Ferry!

Greenport, New York, United States

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Exceptional(4)

$874.58

Welcome to Gull Harbor!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!

SUMMER RETREAT: Beach + Dock overlooking the Peconic Bay in Greenport!

Greenport, New York, United States

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Exceptional(3)

$439.87

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.

Cottage

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

Greenport, New York, United States

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Exceptional(4)

$308.48

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!

5 minute walk to beaches and beautiful downtown Greenport

Greenport, New York, United States

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Three room suite available in a historic home. Large bedroom with a view of the sunrise, bathroom with a clawfoot tub and a bonus room with a kitchenette. Walk to the LIRR and Jitney. Close to all shopping.

Charming and cozy home in the heart of Greenport Village.

Greenport, New York, United States

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$697.47

Beautiful updated historic home in the village of Greenport. Central AC, newly renovated kitchens and bathrooms, large fenced in yard, patio with bbq, outdoor shower, fire pit. Bike to nearby vineyards and beaches and walk to restaurants, stores and bars. Open floor plan with 2 family rooms and dining room + 3 bedrooms and 2 full baths. Bright and well located with off street parking. Many original details including banisters and large wide plank flooring. This unit is part of a 2 family structure. The second unit only overlaps the front main floor room and there are no shared spaces and separate entrances. The other unit is rented year round by a long time resident. brbrI am new to VRBO but a 5 star superhost on Airbnb.

Maritime Village House Walk or Bike to All

Greenport, New York, United States

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*** As we’re brand-new to VRBO, we’re happy to offer our cottage at a reduced rate to our first couple of renters! ***brbrCome stay in our charming vintage cottage, just a three block walk from all the restaurants, bars and bay beaches of Greenport Village! Originally built as the home of the local fire chief in 1929, the cottage has been lovingly restored and updated with central AC and all modern appliances and amenities.brbrThe spacebrThe house has three bedrooms and two remodeled bathrooms, with a screened-in porch, lovely yard and detached garage. All appliances are new and top-of-the-line, including a Wolf range, a large sub-zero refrigerator, central AC and a full washer/dryer. The living room has a 43 Amazon Fire TV, and the whole cottage is wired for fast wireless internet... perfect for working remotely!brbrGuest accessbrAs a guest, you'll have complete access to the cottage, as well as the backyard and driveway. The driveway can accommodate one vehicle comfortably and there is also street parking available.brbrThe Hampton Jitney stops at 476 4th Street (Westbound) and at the LIRR Station (Eastbound). The LIRR stop is a five minute or so walk from the cottage.

Vintage Cottage in Greenport Village

Greenport, New York, United States

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Walk and/or bike everywhere you want from this gem. Rarely rented out, my personal summer rental.brbrBe one of the first to stay in this newly renovated Greenport escape. Centrally located and within close proximity to everything, this house has it all. High speed Internet for your WFH situation. Fully stocked kitchen with KitchenAid appliances. Every bed/pillow in the home is a brand new Casper. Peloton, shuffle board, beach cruisers, SoloStove fire pit, all available for use.brbr*Two week min

Perfect Greenport Retreat

Greenport, New York, United States

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Renovated, waterfront property within close proximity to everything. Outstanding high speed internet, a perfect setup for your families work from home situation, away from home. On-site private gym and a (large) 8-person hot tub. Bars/restaurants/beaches less than a mile from the house.brbr*Village of Greenport laws require a two week minimum rental period for Airbnb hosts and their guests, so please inquire about available discounts for long term rentersbrThe spacebrComplete access to the entire waterfront property and all it’s amenities. Your private oasis.brGuest accessbrThe entire property.....

Waterfront + Complete Gym + Hot tub

Greenport, New York, United States

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$995.61