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.

Condos and Vacation Rentals in Greenport, NY and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    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}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    45 Vacation Rentals in Greenport
    loading...
    From
    $249
    / Night
    Payment Protection
    View Details
    1 / 14
    5 of 5 stars (2) Excellent
    Overview Reviews (2)
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 29
    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    Overview
    From
    $280
    / Night
    Payment Protection
    View Details
    1 / 19
    Greenport
    4 Bedrooms, 9 Bathrooms, Sleeps 8 | Quick View
    Overview
    From
    $165
    / Night
    Payment Protection
    View Details
    1 / 11
    4.5 of 5 stars (2) Very good
    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Overview Reviews (2)
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 16
    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Overview
    From
    $215
    / Night
    View Details
    1 / 23
    4.5 of 5 stars (3) Very good
    Greenport
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
    Overview Reviews (3)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    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
    Make Inquiry
    5 of 5 stars Reviewed September 23, 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 just...
    4 of 5 stars Reviewed October 14, 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 few steep...
    See all reviews
    From
    $409
    / Night
    View Details
    1 / 11
    4.5 of 5 stars (24) Very good
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (24)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    Make Inquiry
    5 of 5 stars Reviewed September 2, 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 liked...
    5 of 5 stars Reviewed June 10, 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
    From
    $489
    / Night
    View Details
    1 / 8
    5 of 5 stars (20) Excellent
    Overview Reviews (20)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    Make Inquiry
    5 of 5 stars Reviewed August 6, 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 with...
    5 of 5 stars Reviewed April 25, 2014
    Great Visit to the Wine Country again....It like going home...Very Clean ...always updated....Great Water Views riight on the Ocean...Great Food & Shopping..
    See all reviews
    From
    $299
    / Night
    Payment Protection
    View Details
    1 / 9
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
    Make Inquiry

    The following rentals are within 5 miles of Greenport, North Fork, Long Island, New York.

    From
    $500
    / Night
    Payment Protection
    View Details
    1 / 11
    3 of 5 stars (1) Average
    Orient
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Overview Reviews (1)
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Grill
    • Internet Access
    • Safe
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Pernchief Cottage Located In The Village Of Orient Is The Perfect Place To Summer With Family And Friends. Front Porch Offers Lovely Views Of The Bay. Wide Pine Floorboards, Great Architectural Detils Abound. Property Is Beautifully Set On 1/2 Acre With Lovely Gardens And A Tranquil Pond. Charming... View all property information
    Make Inquiry
    3 of 5 stars Reviewed May 29, 2014
    Great area but home is in poor condition. Decorated very cute and clean but all uneven floors, very cold inside house, no tv (although it was promised), not worth the price...
    See all reviews
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $190
    / Night
    Payment Protection
    View Details
    1 / 7
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Internet Access
    • Private Fishing...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
    Make Inquiry
    From
    $295
    / Night
    Payment Protection
    View Details
    1 / 17
    5 of 5 stars (11) Excellent
    Southold
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Overview Reviews (11)
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    • Safe
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Bright private sunny renovated three bedroom waterfront house on private street adjoining Arshamamague Pond. The sun is out and all we need is you to complete the picture. Join us at our three bedroom one bath renovated house. Private waterfront. Central AC. Beautiful hardwood floors and... View all property information
    Make Inquiry
    5 of 5 stars Reviewed August 28, 2014
    We had such a wonderful time in Maureen and Alan's cottage. First and foremost, it's on Arshamomaque Pond, which looks like a lake but is actually an inlet of Peconic Bay. It's...
    5 of 5 stars Reviewed July 13, 2014
    My family was very pleased with these accommodations. We were all very comfortable. The place was very clean and well equipped for our 5 day stay. The location is absolutely...
    See all reviews
    From
    $175
    / Night
    Payment Protection
    View Details
    1 / 21
    5 of 5 stars (1) Excellent
    Overview Reviews (1)
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North Fork... View all property information
    Make Inquiry
    5 of 5 stars Reviewed October 14, 2014
    Mark & Mona's historic apartment was a delight. It was small but cozy and clean. Our only surprise was that we didn't realize the bathroom was located inside one of the bedrooms...
    See all reviews
    From
    $175
    / Night
    Payment Protection
    View Details
    1 / 21
    5 of 5 stars (1) Excellent
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (1)
    Amenities & Details
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North... View all property information
    Make Inquiry
    5 of 5 stars Reviewed June 3, 2014
    I rented both units in this cottage a few years back and was pleased to see that the property was lovely as ever. I rented both cottages again this time for a girl’s getaway...
    See all reviews
    From
    $349
    / Night
    Payment Protection
    View Details
    1 / 14
    5 of 5 stars (2) Excellent
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Contemporary 4 bedroom 3 bath house with private Long Island Sound beach access and community tennis and bocce courts in East Marion. Secluded lot with swing set. 2 adult bikes and 2 kids bikes, beach chairs and toys included. Cook's kitchen, large deck. 10 rooms total, including master bedroom... View all property information
    Make Inquiry
    5 of 5 stars Reviewed October 21, 2014
    I stayed here with my wife, young daughter (15 months) and parents for three nights. The house was amazing. It really is a home - as Jane (the owner) had told me, and a big home...
    5 of 5 stars Reviewed September 10, 2014
    The house is warm, cheerful, spacious and bright. It was wonderful to have breakfast, moon-lit dinners on the deck. Indeed the bunnies and deers visited us in the garden as Jane...
    See all reviews
    From
    $150
    / Night
    Payment Protection
    View Details
    1 / 19
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Step back in time as you enter a Historic Home in the heart of Southold....the charm of the historic home is clear as you enter the front door of your unit into the inviting hallway and stairs to the entire upstairs of the home. Just part of the charm is the refinished original 1830 floors, lower... View all property information
    Make Inquiry
    From
    $225
    / Night
    Payment Protection
    View Details
    1 / 18
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Representing the owner's suite is the Unit One apartment in the Historic White Blossom House. Newly renovated, floors, kitchen and bath completely updated. Kitchen updated with period country deep sink and fixtures. You will be very comfortable in this large apartment with living room, family... View all property information
    Make Inquiry
    From
    $299
    / Night
    Payment Protection
    View Details
    1 / 20
    Shelter Island
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Large Shelter Island Farmhouse Close to all - steps from the golf course and beach 46 West Neck Road - overlooks Town Golf Course+ 1 Block to Sunset Beach + Town Boat Launch 3 bedrooms with AC (one queen, 2 twins, bring sheets + towels), 2 baths + outdoor shower, Dining Room, Living Room, Large... View all property information
    Make Inquiry
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 15
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    3 bedrooms, 2 full bathrooms, sleeps 6 Pristine, year round, vacation getaway, within short walk to two white, sandy, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home.... View all property information
    Make Inquiry
    From
    $399
    / Night
    Payment Protection
    View Details
    1 / 26
    Shelter Island
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Beautiful 1875 Historic Shelter Island Heights Gingerbread Victorian Home: 4 bedrooms (we have two master bedrooms with their own porches), 2 baths, plus outdoor shower, large kitchen with double farmhouse sink and new GE washer/dryer, full dining room, large living room with large brick fireplace,... View all property information
    Make Inquiry
    Get the List
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 13
    1 of 5 stars (1) Terrible
    Overview Reviews (1)
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
    Make Inquiry
    1 of 5 stars Reviewed September 2, 2012
    The photos in the add looked good, particularly the garden and the proximity of the lake. We rented the place for four days. When we arrived, the first thing that struck us was...
    See all reviews
    From
    $225
    / Night
    Payment Protection
    View Details
    1 / 12
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview
    Amenities & Details
    • Grill
    • Internet Access
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefront is secluded from neighboring properties and is superb for swimming, boating and fishing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Dine on the... View all property information
    Make Inquiry
    From
    $2,400
    / Week
    Payment Protection
    View Details
    1 / 12
    5 of 5 stars (2) Excellent
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    **New for 2013 Summer: Central Air, Paver Stone Patio Charming, bright, airy, two-bedroom home sits on cozy lot at the heart of the beautiful North Fork, just a minute walk to Southold's most sought after private community beach (Founders Beach). Our beautiful beach features a playground,... View all property information
    Make Inquiry
    From
    $1,400
    / Night
    Payment Protection
    View Details
    1 / 7
    Shelter Island
    6 Bedrooms, 7 Bathrooms, Sleeps 17 | Quick View
    Overview
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    About Seven Newly renovated in 2014, SEVEN offers a selection guest rooms for various combinations of guests, with king, queen, double queen and double twin rooms. Each guestroom includes air conditioning, a flat screen television, light seasonal goose down comforters, 100% cotton linens, and a... View all property information
    Make Inquiry
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 17
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Housekeeping...
    • Internet Access
    • Ocean Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    About this property
    This charming cedar shingled beach cottage is located 45 feet from Long Island Sound with steps leading down to its own private beach. The cottage is surrounded by a wood deck perfect for watching spectacular sunsets...each night, a unique palette of pink, blue and violet sky as the sun drops into... View all property information
    Make Inquiry
    From
    $450
    / Night
    Payment Protection
    View Details
    1 / 5
    East Marion
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    North Fork- East Marion- Charming unique twin cottages with cedar roof and historical significance. Each cottage is new and elegantly appointed. Wide plank flooring and knotty pine doors. Complete kitchen with granite counters and dishwasher. New bath with Italian tiles. Central air conditioning... View all property information
    Make Inquiry
    From
    $250
    / Night
    View Details
    1 / 11
    4.5 of 5 stars (2) Very good
    Southold
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    John Andrew's Cottage is a 'turnkey' experience accommodating two adults and children including: -a cozy bedroom with its full size bed, which beckons you after a sun-filled day at the private beach (within walking distance) which overlooks Shelter Island -a complete kitchen and full bath -a... View all property information
    Make Inquiry
    4 of 5 stars Reviewed August 22, 2014
    my daughter (5 1/2 year old) and i had a great visit here. the cottage was cute and comfortable. having the backyard was great too. the hosts were very friendly and...
    5 of 5 stars Reviewed August 26, 2013
    We stayed at John Andrew’s cottage for my best friend’s bachelorette getaway and loved it. Karen was extremely helpful, had great recommendations all around (The Blue Canoe!) and...
    See all reviews
    From
    $150
    / Night
    View Details
    1 / 11
    4.5 of 5 stars (3) Very good
    Shelter Island
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Overview Reviews (3)
    Amenities & Details
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Our Quaint two bedroom house offers easy access to everything on Shelter Island. Large backyard offers room to kick back or to run around. Bedrooms are comfortable. one with a queen size bed, another with two twins - for those kids of yours, or push them together for a king size bed for extra... View all property information
    Make Inquiry
    4 of 5 stars Reviewed August 16, 2014
    This is a reasonably priced and clean place to stay. The furniture and furnishings are dated from the 60's/70's and it has a slightly musty feel. Other than that, it's a good deal...
    5 of 5 stars Reviewed August 5, 2013
    Everything about this rental was outstanding. The space is clean, airy, as shown in the photos. The yard is large and very beautiful, and the place is peaceful. The location is...
    See all reviews
    From
    $1,300
    / Week
    View Details
    1 / 19
    5 of 5 stars (8) Excellent
    Overview Reviews (8)
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This charming farmhouse is just what you've been looking for: A beautiful, newly renovated 1890's house with all the modern conveniences, perfectly located a few short blocks to Founders Landing Beach Park, Town Beach and Southold Village. About the House The house is a very bright and airy, and... View all property information
    Make Inquiry
    5 of 5 stars Reviewed August 18, 2013
    This is a beautiful, well maintained house· Decorated and furnished to a very high standard. Fantastically situated for the beach in the lovely town of Southold. We used for our...
    See all reviews
    From
    $1,200
    / Night
    View Details
    1 / 16
    4.5 of 5 stars (3) Very good
    Shelter Island
    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    Overview Reviews (3)
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    A time and place you will remember fondly forever. Owned and run by the proprietors of the Trip Advisor #1 rated accomodation on Shelter Island - The House on Chase Creek- this home is not a cottage at all, really, but when built by the Burns Family in 1900 that was what all the vacation homes were... View all property information
    Make Inquiry
    From
    $500
    / Night
    View Details
    1 / 19
    4.5 of 5 stars (2) Very good
    Southold
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Easy to reach, hard to leave! Relax in this charming setting overlooking one of the most beautiful vineyards on The North Fork, complete with a stunning and private sugar sand beach on Southold Bay, one of the best beaches anywhere on the North Fork or The Hamptons, yours to enjoy throughout your... View all property information
    Make Inquiry
    4 of 5 stars Reviewed June 16, 2014
    We found the farmhouse to be charming and spacious for our seven family members. The location was beautiful with the vineyards and private beach, and it was also very handy for...
    See all reviews
    From
    $400
    / Night
    View Details
    1 / 30
    4 of 5 stars (1) Very good
    Shelter Island
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Overview Reviews (1)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    New for 2011-2012 season. We have just installed Martha Stewart wall to wall carpeting on the entire upper level. The third week of August 2011 we replaced the just 8 year old kitchen with a beautiful new kitchen, including professional level stainless steel side by side refrigerator, a 5 burner... View all property information
    Make Inquiry
    4 of 5 stars Reviewed March 24, 2015
    My wife and I are very hard to please when it comes to travel and accommodation. However, Shelter Island Hideaway left us wanting more. The pergola, the décor, the pool, the semi...
    See all reviews
    From
    $499
    / Night
    View Details
    1 / 8
    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and enlarged to double the footprint this winter with new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque inlet in Southold, with... View all property information
    Make Inquiry
    From
    $429
    / Night
    View Details
    1 / 23
    Orient
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy gorgeous water views of Gardiner 's Bay from this immaculate Victorian home situated on 1 acre. This spacious and beautifully decorated home comfortably accommodates 8 adults. Beds: 1 King Bed, 2 Queen Beds, 1 Double Bed View all property information
    Make Inquiry
    From
    $600
    / Night
    View Details
    1 / 35
    Shelter Island
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Contemporary, light filled 3 bedroom, 3 bath home located near South Ferry with easy access to the Hamptons. The lovely open floor plan features an array of contemporary art and sculptures, a living room with vaulted ceiling and fireplace, state-of-the art kitchen and dining room, all having access... View all property information
    Make Inquiry
    From
    $350
    / Night
    View Details
    1 / 16
    Shelter Island
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This eclectic 'Round' house is a one of a kind on Shelter Island. Sited on 1.5 acres in Hay Beach with slices of bay views, this upside down house offers 4 Bedrooms and 2 Baths on the ground floor with an open layout upstairs which includes the living and dining room, kitchen, ½ bath, and covered... View all property information
    Make Inquiry
    From
    $1,167
    / Night
    View Details
    1 / 17
    East Marion
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Escape to a private pastoral compound comprised of a historical home and a guest carriage house sitting on eight lush acres. The main country manor house offers three spacious bedrooms, including an en suite master with an attached private office, 2.5 baths, living, dining, entertaining spaces and... View all property information
    Make Inquiry
    From
    $250
    / Night
    View Details
    1 / 12
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Our immaculate waterview beach house is located in a beach and boating community in Southold, New York, only a mile from the historic village of Greenport. It's the perfect place to relax and take in the North Fork's pristine beaches, award-winning wineries, antique shops, art galleries, and... View all property information
    Make Inquiry
    From
    $314
    / Night
    View Details
    1 / 10
    Orient
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    All newly renovated and exquisitely appointed home sits on a half acre in the private community of Green Acres steps away from the beaches in unspoiled Orient Point. Designer Rena Wilhelm decorated the home in a crisp ‘beachy’ décor. House amenities include central air conditioning, cable TV with... View all property information
    Make Inquiry
    From
    $200
    / Night
    View Details
    1 / 8
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This charming summer cottage is unique in the sense that it is located in the private community of Reydon Shores, and is just walking distance to a private beach and marina. The special feature is its wrap around enclosed porch with a view of the Peconic Bay. If you enjoy the peaceful country... View all property information
    Make Inquiry
    From
    $500
    / Night
    View Details
    1 / 16
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Idyllic retreat in North Fork beach and wine country. Quiet and peaceful, at the end of a private road, our charming, renovated 1830's farmhouse features lots of sunlight, a stainless steel kitchen, all wooden floors, jacuzzi bathtub, mudroom, washer/dryer, wifi, cable tv, air conditioning and... View all property information
    Make Inquiry
    From
    $325
    / Night
    View Details
    1 / 20
    Shelter Island
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    With it's Caribbean flair, 3 waterfalls, 2 pools and 75' Koi pond, our Vacation home is possibly the most Romantic Hamptons Hideaway Vacation Cottage Home Rental ever. Located in the Estate Section of Shelter Island. Available weekly, monthly or for the entire season contact us early for your... View all property information
    Make Inquiry
    From
    $321
    / Night
    View Details
    1 / 5
    Southold
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This Home is located minutes from beautiful Long Island sound beaches, wineries, and historic Greenport village. Whether you enjoy the sun or antiquing everything is hereby. The house was built in 2009, having all modern conveniences but still holding the North Fork charm. The home has a central... View all property information
    Make Inquiry
    From
    $295
    / Night
    View Details
    1 / 11
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable... View all property information
    Make Inquiry
    From
    $295
    / Night
    View Details
    1 / 10
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Newly renovated waterfront cottage with detached studio This property consists of two separate buildings, a two bedroom house with Queen, two twins with pullout beds and the detached studio cottage with queen bed . From September through June only the studio (sleeps 2 + cot for child) is... View all property information
    Make Inquiry