We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Greenport Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $480 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Greenport are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 16 Rentals in Greenport
    Sort by:
    Default
    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    The Farmhouse1 / 10
    (1)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    New North Fork Beach Condo, Pool, Resort, Heart of the Wineries1 / 12
    (24)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Internet Access
    • Terrace
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2014
    6 Girlfriends with children wanted a quick easy trip with no traffic to end the summer. We got exactly that! The Cliffside Resort was perfect. I honestly can't say what I...
    Reviewed 11 June 2014
    My son got married this past weekend at a Vineyard near Cliffside and my family, the bride's family and some guests spent the weekend there. In total, we rented about 23 units...
    See all reviews
    About this property
    Beautiful 2 Bedroom 2 Bathroom Poolside Unit. All that Cliffside Resort and the Sound have to offer are just steps away. Additional amenities include: close to town, in-room entertainment system, kitchenette, private walkway to the sound, refrigerated wine cooler, on sound, washer & dryer...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Cliffside Resort Greenport Luxurious Waterfront Condo- with Pool!1 / 8
    (33)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Terrace
    • Internet Access
    • Satellite TV
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2015
    My college friends & I have been coming here for @ 6 years...nowhere better....the condo is clean and nicely decorated......if you choose water view/front...well worth the...
    Reviewed 6 August 2014
    Enjoyed four night stay .condo unit &entire complex was clean and well maintained.Location was perfect for touring vineyards ,Shelter Island and Greenport attractions.Pool...
    See all reviews
    About this property
    As featured by New York Magazine, the Cliffside Resort entertains the perfect vacation! This 68 unit complex, located directly on the Long Island Sound with incredible sunset views, offers brand new 2 bedroom 2 bathroom luxurious accommodations. Cliffside Resort Waterfront Condominiums at...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elegant and especially designed and built for one of the wealthiest bankers on the North Fork. Situated on enormous 3/4 acre property in the most prestigious setting of the National Historic District in Greenport Village. Lovingly restored to its original elegance and authentic Classic Queen...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the historic seaport of Greenport Village from this recently remodeled 1-bedroom, 1-bathroom vacation rental apartment that comfortably sleeps 2. Located in the heart of downtown, you won’t find a better location to explore all the area has to offer than from this charming apartment. Only 2...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will love this 4 bedroom 4.5 bathroom charmer on a quiet street. Walk to town, shops, carousel LIRR Jitney and ferry to Shelter Island Golf course and beaches 1 mile away. There are over 40 wineries nearby. The front deck has 2 Adirondack chairs to just relax. A full deck off the back over...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
    Make Enquiry
    Family and Friends in Greenport1 / 23
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Housekeeping Included
    • DVD Player
    • Balcony
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 2014
    The pictures of this house do not do it justice. It is spacious although an older home, with wide floorboards, a great room with fireplace, toys for kids, deck for eating or...
    Reviewed 15 October 2013
    We just returned from renting for Columbus weekend. Very happy with the house. We needed a ground floor room & shower for my 88yr old Mother & this worked out perfect. A...
    See all reviews
    About this property
    Our house is an historic Dutch colonial, both cozy and spacious, with warm wood trim and wood floors throughout. The 20 x 20ft. Great Room, a perfect gathering space for family and friends is complete with a baby grand piano, cable TV, children's toys and books, classic novels and wood burning...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, private parking, a kayak, two bicycles, public swimming dock at end of block, and is one...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Save time - get the best Greenport rentals sent straight to your email!
    Get the List
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic Greenport Village has been recently renovated and is in walking distance to all. This is a 2 family home that can be rented separately or together. Pricing here is for house 2. One bedroom has a queen and the other can be configured as a king or two twins. Parking, beach access, convenient...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Air Conditioning
    • Balcony
    • Porch
    • Wi-Fi
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Entirely renovated, spacious and quiet farmhouse two blocks from the marina, and a 5 minute bike ride to the beach or town. With original hardwood floors, modern kitchen with Viking appliances, two fireplaces, grill, and al fresco dining under a pergola. Located in Greenport, NY, the middle of wine...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the scenic seaside village of Greenport in this 2-bedroom, 2-bathroom vacation rental apartment that comfortably sleeps 4. Located in the heart of Greenport Village, enjoy quick access to fine restaurants, exceptional shopping and numerous local attractions. Boasting 1,850 square-feet of...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Parking
    • Grill
    • Children's Pool
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic home in Greenport Village walking distance to restaurants, water, shopping etc..bike or short drive from vineyards. Large yard with outdoor patio with BBQ and outdoor shower. 2 family home with two separate duplex units that can be rented separately or together. Perfect for family...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walking distance to Greenport Village, Sound and Bay Beaches! 1200 sq ft Victorian cottage perfect for a retreat from the heat. Large patio, new kitchen and bath! 1840s historic poet's house, perfect for couples, small family or single seeking reprieve from Manhattan. Original hardwood floors, 2...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the charming seaside village of Greenport from this quaint 1-bedroom, 1-bathroom vacation rental apartment with sleeping accommodations for 2. Only a couple of blocks from downtown, enjoy quick access to numerous restaurants, boutique shops and local attractions. Your ultimate North Fork...
    View all property information
    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property
    Owner log in