Home Vacation Rentals By Owner In Greenport, NY

Showing 20 Of 132 Vacation Rentals
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Exceptional(98)

$764.88

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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 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.brbr
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Bath 2

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Sleep 6

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Exceptional(118)

$657.13

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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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Bath 3

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Sleep 4

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Exceptional(2)

$2418.54

/ Nightly
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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Bath 6

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Sleep 10

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Exceptional(16)

$307.24

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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.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
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Sleep 6

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$995.61

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Private Vacation Home

Greenport Log Home in the woods. Pool&water access. GP Permit #0952

Greenport, New York, United States

PLEASE READ FULL DESCRIPTION! Rental registry # 0952brPool coming summer 2025!!!!Private modern 4 bedroom/2 bath cabin near the bay situated on 3.8 acres on culdesac. The cabin is set 200 ft off a quiet culdesac 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! brPublic 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! brbr7 person Hot tubbrbrAir hockey and foosball tables brbr2 separate TV rooms. brbrWill not rent without first having contact and discussion with potential tenant. ** 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! brMin stay requirements- please ask before bookingbrSpecial woodland living near the water.brbrRates- brPlease refer to calendarbrDiscounts given for long term rentals- 30 days or morebrbrbrPreference is given to long term rentalsbrbrBe sure that you have looked at all of the pictures for the property … let me know if you have any “questions” br**Some periods may be blocked on calendar for family use of the log home. These can often be switched around to accommodate potential rentals if needed. Priority given to LONG TERM summer season inquiries. DISCOUNT available for 30 day or longer. Suffolk County Hotel tax will apply as well. I’m sorry, but the county makes me collect this for rentals under 30 days.
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