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Holiday Rentals and Villas in Shelter Island, NY and nearby

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    60 Holiday Rentals in Shelter Island
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    From
    £268
    / Night
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    1 / 26
    Shelter Island
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    From
    £201
    / Night
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    1 / 20
    Shelter Island
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    From
    £941
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    1 / 7
    Shelter Island
    6 Bedrooms, 7 Bathrooms, Sleeps 17 | Quick View
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    From
    £101
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    1 / 11
    4.5 of 5 stars (3) Very good
    Shelter Island
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Overview Reviews (3)
    From
    £807
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    1 / 16
    4.5 of 5 stars (3) Very good
    Shelter Island
    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    Overview Reviews (3)
    From
    £403
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    1 / 35
    Shelter Island
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    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
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    From
    £269
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    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
    • Grill
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • 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
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    4 of 5 stars Reviewed 24 March 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...
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    £235
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    1 / 16
    Shelter Island
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • 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
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    From
    £218
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    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
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    The following rentals are within 10 kilometres of Shelter Island, Long Island, New York.

    From
    £202
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    1 / 29
    Greenport, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    The Space Located on a tree lined street this sun-filled two story house sleeps 8 people +. It features 3 bedrooms, 2 bathrooms, an eat in-kitchen and spacious living area with TV and wifi. There are 2 queen size beds, 2 full size beds and a queen size sleeper sofa. The private backyard offers... View all property information
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    From
    £128
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    1 / 7
    Southold, NY
    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
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    From
    £188
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    1 / 19
    Greenport, NY
    4 Bedrooms, 9 Bathrooms, Sleeps 8 | Quick View
    Overview
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    • Air Conditioning
    • Balcony
    • Grill
    • Safe
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
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    About this property
    A gem of a getaway! There are four bedrooms, of which three are located upstairs. Two of the upstairs bedrooms share one new en-suite bathroom. One bedroom upstairs has it's own en-suite bathroom. The bedroom on the ground floor has an en-suite water closet and another full bathroom. The cottage... View all property information
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    From
    £807
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    1 / 17
    Sag Harbor
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Grill
    • Safe
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
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    About this property
    THE PERFECT HAMPTONS LOCATION, VILLAGE AND BEACHES Simply the best location in the Hamptons, this house is a short walk to the beautiful village of Sag Harbor, but hidden away in a forest of trees, and extremely quiet and private. This unique designer house is filled with natural light and... View all property information
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    From
    £198
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    1 / 17
    5 of 5 stars (11) Excellent
    Southold, NY
    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
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    5 of 5 stars Reviewed 28 August 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 14 July 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...
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    £672
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    1 / 7
    Sag Harbor
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    OPEN HOUSE!! Sunday May 18 One of the last houses in the area with pool AND tennis! MD-LD $60,000 Please call first. Welcome to my paradise! My home has everything you need for a fantastic summer. 6 bedroom/4 bath contemporary home on 10 secluded acres. Heated in ground 20x40 pool, all weather... View all property information
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    From
    £118
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    1 / 21
    5 of 5 stars (1) Excellent
    Southold, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    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
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    5 of 5 stars Reviewed 15 October 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...
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    £167
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    1 / 14
    5 of 5 stars (2) Excellent
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Private Fishing...
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Overview: 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. Quoted rental rates include all taxes. Details: Offered by... View all property information
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    5 of 5 stars Reviewed 17 September 2014
    My friends and I really enjoyed our stay here. VERY clean, comfortable and the location was perfect for our visits to the local wineries. The private beach was very clean and we...
    5 of 5 stars Reviewed 9 August 2014
    Terrific Two bedroom condo on the water. Was there for July 4th, tons to do. Minutes from shelter island and views to die for.
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    £118
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    1 / 21
    5 of 5 stars (1) Excellent
    Southold, NY
    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
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    5 of 5 stars Reviewed 3 June 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...
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    £235
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    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
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    5 of 5 stars Reviewed 21 October 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 11 September 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...
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    From
    £33,610
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    1 / 18
    Sag Harbor
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Overview
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    The feeling of Zen surrounds you as you enter upon this European designer's hideaway..Custom appointments of quality and luxury fill this Hampton's home. Located 12 minutes walk to Main Street of the prestigious Sag Harbor Village....0.4 acres of beautifully manicured totally private lawns with... View all property information
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    From
    £101
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    1 / 19
    Southold, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview
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    • 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
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    £2,017
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    1 / 4
    Sag Harbor
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Dryer
    • Private Outdoor...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Located in the quaint historic whaling Village of Sag Harbor, 12 minute walking distance to the center of town, with close proximity to the bay and ocean beaches. This European designer's home totals 5000 sq.ft., the lower level just shy of 1000, sq ft and is the designer's private lower level... View all property information
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    £202
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    1 / 15
    Southold, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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
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    £151
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    1 / 18
    Southold, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview
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    • 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
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    £10,083
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    1 / 9
    Sag Harbor
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Minutes from Sag Harbor Village, beaches, and steps to Sag Harbor Cove. This charming 3 bedroom cottage is situated on a quiet dead end street.. Living room with fireplace, family room with hand hewn beams, sunny eat-in-kitchen, wide pine flooring,and CAC. This half acre property has a heated... View all property information
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    £1,512
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    1 / 27
    5 of 5 stars (4) Excellent
    Sag Harbor
    5 Bedrooms, 8 Bathrooms, Sleeps 10 | Quick View
    Overview Reviews (4)
    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
    About this property
    This property is only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is one month during High Season unless you see an availability between rentals. During the off season 2 week rentals may be possible. This elegant 6000... View all property information
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    £111
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    1 / 11
    4.5 of 5 stars (2) Very good
    Greenport, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Overview Reviews (2)
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Our one bedroom,kitchenette/ dining room & foldout queen size couch in living downstairs sleeps four comfortable . Backyard garden. Just forty yard walk to our block pier. 150 yard walk into town. The heart of Greenport Village on the best block in our Village no need for your once you arrive... View all property information
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    4 of 5 stars Reviewed 4 December 2014
    The place is in a great location - a short walk to downtown Greenport but far enough to have some peace and quiet. The apartment itself is nicely furnished and is charming. Keep...
    5 of 5 stars Reviewed 29 August 2014
    I hate to let anyone know about this place since my family (husband and two teenagers) had such a wonderful time and want to return next year and worry that if people discover...
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    £336
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    1 / 10
    5 of 5 stars (3) Excellent
    Sag Harbor
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (3)
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Beech Tree Cottage is a charming two-bedroom, one-bath guest cottage conveniently located in the historic district of Sag Harbor, NY - a 5-minute walk along the waterfront to Main Street and the center of the village. The beach is a short drive or bike ride away. The owners are full-time residents... View all property information
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    From
    £198
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    1 / 21
    5 of 5 stars (3) Excellent
    Overview Reviews (3)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    From its commanding position on Main Street in the heart of Sag Harbor village, this spectacular vintage Victorian is an authentic testament to the history of Sag Harbor. With distinctive architecture and classic styling, the impressive house features the Upstairs Apartment with five rooms,... View all property information
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    £302
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    1 / 5
    East Marion, NY
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • 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
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    £168
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    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
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    1 of 5 stars Reviewed 2 September 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...
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    £151
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    1 / 12
    Southold, NY
    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
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    From
    £840
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    Sag Harbor
    7 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Air Conditioning
    • Dishwasher
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    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    About this property
    25 year age limit...please don't inquire if you do not meet the age requirements, you will be wasting your time and ours. Drive through private gates to this secluded property with 7 over sized bedrooms; 5 baths. The house is an architect's resort-inspired vacation home. The property sits on a 2+... View all property information
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    1 / 16
    Greenport, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    The Space The Old Schoolhouse tells a family story, dating back to the 1880's. This charming farmhouse, built by the Burt family in the 1880's, was first used as a schoolhouse, then transformed into a farmhouse. The Burt family updated the house in 2005 with the most energy efficient systems, so... View all property information
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    1 / 11
    Southold, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • 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
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    Sag Harbor
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    • x
    • x
    About this property
    PHEASANT ESCAPE GUEST SUITE An Accommodation for Particular People. Escape to Nature Without Roughing It. INFANTS and CHILDREN ALWAYS WELCOME. Special Promotion Option A: Stay 2 weekdays and get 25% off the 2nd weeknight. Special Promotion Option B: Stay 3 weekdays and get 50% off the 3rd... View all property information
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    1 / 27
    Sag Harbor
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy the historic and beautiful town of Sag Harbor while staying in a modern, comfortable and family friendly home with amazing hilltop views. Bring the whole family, the house comfortably sleeps 8-10.The home is set within two miles from Sag Harbor Village and less than a mile walk to the bay... View all property information
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    Sag Harbor
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
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    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    About this property
    Read the article in Newsday about one of my houses, by Alex Mc Cord of the Real Housewives of NY ,She has been renting from me every time she is out here. THIS home was also written up in the NY Post Earlier this year in an article on June 24th 2010 called 'Be My Guest' as new great places to stay!... View all property information
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    Sag Harbor
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Private Fishing...
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Redwood Cottage has two bedrooms each with a queen size bed. One bathroom with tub/shower. It overlooks the Upper Cove in the Village of Sag Harbor. It is very nicely decorated inside with a full kitchen, dinning room, lovely living room with a water view! It is within walking distance of the... View all property information
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    1 / 5
    Southold, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • 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
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    1 / 12
    5 of 5 stars (2) Excellent
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
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    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • 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
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    £605
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    1 / 17
    Sag Harbor
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Walk in to the view of the sky and bay through the living room. The master suite is its own floor. the house is modern, there are three other bedrooms. Perfect home for a summer vacation. A short ride to Main Street, Sag Harbor, short walk to bay beach. View all property information
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    1 / 17
    Southold, NY
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • 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
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    £1,344
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    1 / 12
    Sag Harbor
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Overview
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Beautiful waterfront estate with beach, boat dock, pond, minutes to Sag Harbor, in the heart of the Hamptons. Three acre manicured property. Fantastic view of boats cruising Shelter Island Sound. Walk to village playground, tennis, basketball, and hiking trails. Available for Memorial Day to... View all property information
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    £198
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    1 / 10
    Southold, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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 and a detached studio cottage . From September through June only the studio (sleeps 2) is available for rent. In July and August both the 2 bedroom cottage and the studio... View all property information
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    £336
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    1 / 10
    Sag Harbor
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    85 Milton Ave is a charming, comfortable family home where warm memories are made. Enjoy the house, beach and historic Sag Harbor from the conveniently located residence. The 1 mile walk to town is down pristine lanes past beautifully landscaped homes and water views. Sag Harbor was the first... View all property information
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    £168
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    4.5 of 5 stars (2) Very good
    Southold, NY
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (2)
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    • 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
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    4 of 5 stars Reviewed 22 August 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 26 August 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...
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    £202
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    Overview Reviews (4)
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Forever Cottage is a charming, one-bedroom guest cottage plus newly added separate, modern 'boutique' Studio which rents separately, just steps from Main Street in the scenic village of Sag Harbor, NY, available to rent for weeks, weekends or longer stays- year-round. Sag Harbor is a beautiful,... View all property information
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    5 of 5 stars Reviewed 18 September 2014
    After spending our first night out in the Hamptons at what was described as a luxury hotel which turned out to be a 1960's rehabbed motel we were THRILLED when we got to our...
    5 of 5 stars Reviewed 13 August 2011
    This cottage was charming and centrally located. The owner lives near by and was very sweet and helpful. It rained the whole time we were there, but even so, we had the best...
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    4.5 of 5 stars (3) Very good
    Greenport, NY
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
    Overview Reviews (3)
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    • 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
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    5 of 5 stars 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 just...
    4 of 5 stars 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 few steep...
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    £151
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    1 / 18
    Southold, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview
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    • 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
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