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Vacation Rentals in Orient, NY and nearby

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    All 65 Rentals in the Orient Area
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    $500
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    1 / 11
    3 of 5 stars (1) Average
    Orient
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    travelers have booked this property
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    $429
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    1 / 23
    Orient
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    $314
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    Orient
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    The following rentals are within 10 miles of Orient, North Fork, Long Island, New York.

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    1 / 29
    Greenport
    3 Bedrooms / 2 Bathrooms / Sleeps 9
    traveler have booked this property
    Overview Make Inquiry
    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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    $190
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    1 / 7
    Southold
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    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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    $250
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    1 / 16
    Greenport
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    traveler have booked this property
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    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
    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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    $280
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    1 / 19
    Greenport
    4 Bedrooms / 9 Bathrooms / Sleeps 8
    travelers have booked this property
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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
    • x
    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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    1 / 14
    5 of 5 stars (2) Excellent
    Greenport
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    • 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 September 17, 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 August 8, 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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    $145
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    1 / 11
    4.5 of 5 stars (2) Very good
    Greenport
    3 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
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    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 December 3, 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 August 29, 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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    1 / 14
    5 of 5 stars (2) Excellent
    East Marion
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travelers have booked this property
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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
    • ?
    • 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 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...
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    $175
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    1 / 21
    5 of 5 stars (1) Excellent
    Southold
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    • 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 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...
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    1 / 21
    5 of 5 stars (1) Excellent
    Southold
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    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 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...
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    1 / 19
    Southold
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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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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    1 / 18
    Sag Harbor
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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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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    $900
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    1 / 17
    Sag Harbor
    4 Bedrooms / 3 Bathrooms / Sleeps 6
    travelers have booked this property
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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 / 4
    Sag Harbor
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Dryer
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    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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    $1,250
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    1 / 32
    Sag Harbor
    7 Bedrooms / 5 Bathrooms / Sleeps 14
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    • 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
    • ?
    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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    $225
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    1 / 18
    Southold
    2 Bedrooms / 1 Bathroom / Sleeps 4
    traveler have booked this property
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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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    $2,250
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    1 / 27
    5 of 5 stars (4) Excellent
    Sag Harbor
    5 Bedrooms / 8 Bathrooms / Sleeps 10
    travelers have booked this property
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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
    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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    $295
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    1 / 17
    5 of 5 stars (11) Excellent
    Southold
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
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    • 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 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...
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    1 / 10
    5 of 5 stars (3) Excellent
    Sag Harbor
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • 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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    1 / 15
    Southold
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • 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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    1 / 21
    5 of 5 stars (3) Excellent
    Sag Harbor
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
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    • 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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    1 / 13
    1 of 5 stars (1) Terrible
    Southold
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • 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 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...
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    1 / 7
    Shelter Island
    6 Bedrooms / 7 Bathrooms / Sleeps 17
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
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    • x
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    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
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    $225
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    1 / 12
    Southold
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    • 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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    $399
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    1 / 16
    Shelter Island
    4 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Pets allowed
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    • ?
    • x
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    • Elder access
    • 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
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    $299
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    1 / 7
    Shelter Island
    3 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Pets allowed
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    • x
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    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
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    1 / 12
    Sag Harbor
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Internet Access
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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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    $499
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    1 / 8
    Southold
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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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
    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
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    $150
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    1 / 6
    Sag Harbor
    1 Bedroom / 2 Bathrooms / Sleeps 3
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    • Balcony
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    • Pets allowed
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    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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    1 / 7
    Sag Harbor
    Studio / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dishwasher
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    • Hot Tub
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    • Private Fishing...
    • Safe
    • Satellite TV
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    • ?
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    • x
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    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 / 27
    Sag Harbor
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    traveler have booked this property
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    • Air Conditioning
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    • Dryer
    • Fireplace
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    • Internet Access
    • Mountain Views
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • x
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    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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    1 / 12
    5 of 5 stars (2) Excellent
    Southold
    2 Bedrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    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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    Shelter Island
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
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    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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    1 / 7
    Sag Harbor
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Pets allowed
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    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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    1 / 12
    Sag Harbor
    4 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • ?
    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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    1 / 22
    5 of 5 stars (1) Excellent
    Sag Harbor
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Inquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
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    • Elder access
    • x
    About this property
    This lovely 3 bedroom, 2 bath home in the Village of Sag Harbor is located conveniently 1 mile from Sag Harbor's Main Street and a 1/2 mile to Haven's Beach,1 mile to public golf course and 10 min to Sag Main Ocean. No car necessary, you can hop a bus anywhere on the East End and North Forks! This... View all property information
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    1 / 10
    Sag Harbor
    3 Bedrooms / 1 Bathroom / Sleeps 8
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    • Air Conditioning
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    • Grill
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    • Private Fishing...
    • Satellite TV
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • 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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    1 / 35
    Shelter Island
    3 Bedrooms / 3 Bathrooms / Sleeps 5
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • x
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    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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    1 / 11
    4.5 of 5 stars (2) Very good
    Southold
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    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 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...
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    1 / 19
    5 of 5 stars (4) Excellent
    Sag Harbor
    1 Bedroom / 1 Bathroom / Sleeps 3
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    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
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    • 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 September 18, 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 August 12, 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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    1 / 23
    4.5 of 5 stars (3) Very good
    Greenport
    4 Bedrooms / 2 Bathrooms / Sleeps 11
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • 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 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...
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    1 / 11
    4.5 of 5 stars (3) Very good
    Shelter Island
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    Amenities & Details
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
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    • 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
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    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...
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    1 / 16
    Shelter Island
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • 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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    $1,300
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    1 / 19
    5 of 5 stars (8) Excellent
    Southold
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • 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
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    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...
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    1 / 16
    4.5 of 5 stars (3) Very good
    Shelter Island
    5 Bedrooms / 3 Bathrooms / Sleeps 9
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
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    • x
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    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
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    1 / 19
    4.5 of 5 stars (2) Very good
    Southold
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • 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
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    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...
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    1 / 30
    4 of 5 stars (1) Very good
    Shelter Island
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Inquiry
    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 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...
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    1 / 7
    5 of 5 stars (1) Excellent
    Sag Harbor
    5 Bedrooms / 3 Bathrooms / Sleeps 16
    Overview Reviews (1) Make Inquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
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    About this property
    GREAT HOUSE FOR A GATHERING OF FRIENDS OR FAMILY LARGE YARD, 50 FOOT POOL, HOT TUB KITCHEN WITH GRANITE COUNTER TOPS GREAT LIVING ROOM WITH LARGE SCREEN HDTV, GOLD CABLE, WIFI 5+ 2 MORE BEDROOMS SHORT DRIVE/BIKE TO SAG HARBOR VILLAGE OR OCEAN BEACHES. Beds: 4 King Beds, 2 Double... View all property information
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    5 of 5 stars Reviewed October 4, 2014
    Hawk Haven is a wonderful escape, ideal for relaxing away from it all . Wild turkeys and deer gather on the vast lawn in the early evening and it is hard to believe you are right...
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