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Vacation Rentals in Shelter Island, NY and nearby

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All 60 Rentals in the Shelter Island Area
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From
$299
Per Night
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1 / 7
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Shelter Island
3 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
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From
$399
Per Night
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1 / 16
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Shelter Island
4 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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From
$1,400
Per Night
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1 / 7
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Shelter Island
6 Bedrooms, 7 Bathrooms, Sleeps 17
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From
$150
Per Night
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1 / 11
Shelter Island
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (3) Make Inquiry
Amenities & Details
  • Satellite TV
  • Parking
  • Stove
  • Linens Provided
  • Washer
  • Grill
  • Internet Access
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • 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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From
$1,200
Per Night
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1 / 16
Shelter Island
5 Bedrooms, 3 Bathrooms, Sleeps 9
Details Reviews (3) Make Inquiry
Amenities & Details
  • DVD Player
  • Refrigerator
  • Stereo System
  • Stove
  • Patio
  • Fireplace
  • Dishwasher
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
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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From
$600
Per Night
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1 / 35
Shelter Island
3 Bedrooms, 3 Bathrooms, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Garage
  • Stove
  • Stereo System
  • Fireplace
  • Washer
  • Grill
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
$325
Per Night
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1 / 20
Shelter Island
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Stove
  • Patio
  • Fireplace
  • Grill
  • Parking
  • Dishwasher
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • 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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From
$400
Per Night
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1 / 30
Shelter Island
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Parking
  • Hot Tub
  • Washer
  • Patio
  • DVD Player
  • Fireplace
  • Refrigerator
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • 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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From
$350
Per Night
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1 / 16
Shelter Island
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Patio
  • Refrigerator
  • Parking
  • Garage
  • Fireplace
  • DVD Player
  • Dishwasher
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • 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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The following rentals are within 5 miles of Shelter Island, Long Island, New York.

From
$500
Per Night
View Details
1 / 10
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Sag Harbor
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (3) Make Inquiry
Amenities & Details
  • Stereo System
  • Parking
  • Stove
  • Playground
  • Microwave
  • TV
  • DVD Player
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • 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
$300
Per Night
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1 / 29
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Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 9
Booking
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Amenities & Details
  • Grill
  • Wi-Fi
  • Washer
  • Stove
  • Deck
  • TV
  • Dishwasher
  • Porch
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • 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
$250
Per Night
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1 / 7
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Fireplace
  • Internet Access
  • Microwave
  • Ceiling Fans
  • Waterfront
  • VCR
  • Stove
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
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
$280
Per Night
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1 / 19
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Greenport, NY
4 Bedrooms, 9 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Grill
  • Central Heating
  • Private Yard
  • Linens Provided
  • Parking
  • Terrace
  • Safe
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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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From
$249
Per Night
View Details
1 / 14
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Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • TV
  • Satellite TV
  • Refrigerator
  • Deck
  • Dryer
  • Grill
  • Dishwasher
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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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From
$249
Per Night
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1 / 14
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East Marion, NY
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Microwave
  • Patio
  • Refrigerator
  • TV
  • Grill
  • Garage
  • Washer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • 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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From
$2,250
Per Night
View Details
1 / 27
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Sag Harbor
5 Bedrooms, 8 Bathrooms, Sleeps 10
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Grill
  • Stove
  • TV
  • Fireplace
  • Dishwasher
  • DVD Player
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • Smoking allowed
  • Elder access
  • x
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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From
$175
Per Night
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1 / 21
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • DVD Player
  • Microwave
  • Ceiling Fans
  • Refrigerator
  • Stove
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
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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From
$175
Per Night
View Details
1 / 21
Payment Protection
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • DVD Player
  • Parking
  • Washer
  • Grill
  • Dryer
  • Microwave
  • TV
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North... View all property information
Make Inquiry
5 of 5 stars Reviewed June 3, 2014
I rented both units in this cottage a few years back and was pleased to see that the property was lovely as ever. I rented both cottages again this time for a girl’s getaway...
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From
$295
Per Night
View Details
1 / 21
Payment Protection
Sag Harbor
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Dishwasher
  • TV
  • Stove
  • Air Conditioning
  • Refrigerator
  • Dryer
  • Parking
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$295
Per Night
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1 / 12
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Sag Harbor
Studio, 1 Bathroom, Sleeps 2
Details Make Inquiry
Amenities & Details
  • DVD Player
  • TV
  • Microwave
  • Stereo System
  • Satellite TV
  • Parking
  • Internet Access
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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From
$300
Per Night
View Details
1 / 15
Payment Protection
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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From
$150
Per Night
View Details
1 / 19
Payment Protection
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Internet Access
  • Satellite TV
  • TV
  • Washer
  • Refrigerator
  • Stove
  • Patio
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • 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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From
$2,000
Per Night
View Details
1 / 18
Payment Protection
Sag Harbor
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Fireplace
  • Washer
  • Patio
  • Parking
  • Stove
  • Microwave
  • TV
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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
$225
Per Night
View Details
1 / 18
Payment Protection
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • TV
  • Microwave
  • Ceiling Fans
  • Safe
  • Dryer
  • Refrigerator
  • Stove
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$400
Per Night
View Details
1 / 27
Payment Protection
Sag Harbor
4 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
Details Make Inquiry
Amenities & Details
  • Grill
  • Stove
  • TV
  • Washer
  • Patio
  • Parking
  • Dishwasher
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • 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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From
$3,000
Per Week
View Details
1 / 4
Payment Protection
Sag Harbor
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Inquiry
Amenities & Details
  • Stove
  • Microwave
  • Patio
  • Parking
  • Washer
  • TV
  • Air Conditioning
  • Linens Provided
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • 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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From
$295
Per Night
View Details
1 / 17
Payment Protection
Southold, NY
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (11) Make Inquiry
Amenities & Details
  • Patio
  • Safe
  • Ceiling Fans
  • Grill
  • Microwave
  • Dishwasher
  • Refrigerator
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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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From
$250
Per Night
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1 / 13
Payment Protection
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Inquiry
Amenities & Details
  • Waterfront
  • VCR
  • Satellite TV
  • Ceiling Fans
  • DVD Player
  • Refrigerator
  • Water Views
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
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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From
$225
Per Night
View Details
1 / 12
Payment Protection
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Parking
  • Waterfront
  • Water Views
  • Microwave
  • Patio
  • Stove
  • Deck
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
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
$450
Per Night
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1 / 5
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East Marion, NY
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Inquiry
Amenities & Details
  • TV
  • Patio
  • Stove
  • Air Conditioning
  • Wi-Fi
  • Refrigerator
  • Grill
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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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From
$145
Per Night
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1 / 11
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Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Satellite TV
  • Ceiling Fans
  • Grill
  • Safe
  • Dishwasher
  • Porch
  • Internet Access
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • 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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From
$250
Per Night
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1 / 16
Payment Protection
Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 7
Booking
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Stove
  • Dryer
  • Deck
  • Grill
  • Parking
  • Microwave
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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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From
$200
Per Night
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1 / 6
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Sag Harbor
1 Bedroom, 2 Bathrooms, Sleeps 3
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Amenities & Details
  • Grill
  • Ceiling Fans
  • Parking
  • Refrigerator
  • Washer
  • Patio
  • DVD Player
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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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From
$375
Per Night
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1 / 7
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Sag Harbor
Studio, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Hot Tub
  • Refrigerator
  • TV
  • Safe
  • VCR
  • Grill
  • Dishwasher
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • 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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$650
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Sag Harbor
3 Bedrooms, 4 Bathrooms, Sleeps 6
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Amenities & Details
  • Safe
  • Grill
  • Private Yard
  • Air Conditioning
  • Towels Provided
  • Central Heating
  • Linens Provided
  • Wi-Fi
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
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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$2,400
Per Week
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Southold, NY
2 Bedrooms, Sleeps 6
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Amenities & Details
  • Fireplace
  • Stereo System
  • DVD Player
  • Grill
  • Dishwasher
  • Microwave
  • TV
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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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$1,250
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Sag Harbor
7 Bedrooms, 5 Bathrooms, Sleeps 14
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Amenities & Details
  • Grill
  • Patio
  • Dishwasher
  • Fireplace
  • Microwave
  • Hot Tub
  • Washer
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
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+ acre lot for complete and utter privacy. Beautifully Landscaped with a Koi Pond. 75'L-shaped heated pool, hot tub, outdoor... View all property information
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$900
Per Night
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Sag Harbor
4 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • TV
  • Washer
  • Stove
  • Patio
  • Microwave
  • Grill
  • Refrigerator
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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$1,000
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Sag Harbor
6 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
$300
Per Night
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1 / 40
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Grill
  • Dryer
  • TV
  • Refrigerator
  • Stove
  • Parking
  • Microwave
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Come experience a Northfork summer, golfing, biking, beaching, Estate sale hunting, in the Heart of Wine Country, Long Island. Centrally Located in the Town of Southold, South of the main road, 3 houses from the water in the elite Founders Landing section of North Fork, The cottage is minutes'... View all property information
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$500
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Sag Harbor
3 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • DVD Player
  • Washer
  • Stereo System
  • Stove
  • Dryer
  • Grill
  • Dishwasher
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
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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From
$2,000
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Sag Harbor
4 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • DVD Player
  • Sauna
  • Washer
  • Stove
  • Fireplace
  • Microwave
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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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$500
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1 / 10
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Sag Harbor
3 Bedrooms, 1 Bathroom, Sleeps 8
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Amenities & Details
  • Stove
  • Playground
  • Patio
  • Dishwasher
  • Refrigerator
  • Parking
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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$250
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1 / 11
Southold, NY
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Stove
  • Parking
  • Air Conditioning
  • DVD Player
  • TV
  • Satellite TV
  • VCR
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 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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$250
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1 / 19
Sag Harbor
1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Stove
  • Patio
  • VCR
  • Refrigerator
  • Microwave
  • DVD Player
  • Fireplace
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • 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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$1,300
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1 / 19
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • Dryer
  • Grill
  • DVD Player
  • Stereo System
  • Dishwasher
  • Refrigerator
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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$215
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1 / 23
Greenport, NY
4 Bedrooms, 2 Bathrooms, Sleeps 11
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Amenities & Details
  • Parking
  • Grill
  • Washer
  • TV
  • Dryer
  • Microwave
  • Dishwasher
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • 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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From
$500
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1 / 19
Southold, NY
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Grill
  • Microwave
  • Dishwasher
  • Garage
  • Dryer
  • Washer
  • Stove
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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$1,000
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1 / 7
Sag Harbor
5 Bedrooms, 3 Bathrooms, Sleeps 16
Details Reviews (1) Make Inquiry
Amenities & Details
  • Stereo System
  • Fireplace
  • Microwave
  • Refrigerator
  • Dishwasher
  • Stove
  • Hot Tub
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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$489
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1 / 4
Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Terrace
  • Private Outdoor...
  • Refrigerator
  • Microwave
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
As featured by New York Magazine, the Cliffside Resort entertains the perfect vacation! This 68 unit complex, located directly on the Long Island Sound with incredible sunset views, offers brand new 2 bedroom 2 bathroom luxurious accommodations. Cliffside Resort Waterfront Condominiums at... View all property information
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5 of 5 stars Reviewed August 6, 2014
Enjoyed four night stay .condo unit &entire complex was clean and well maintained.Location was perfect for touring vineyards ,Shelter Island and Greenport attractions.Pool with...
5 of 5 stars Reviewed April 25, 2014
Great Visit to the Wine Country again....It like going home...Very Clean ...always updated....Great Water Views riight on the Ocean...Great Food & Shopping..
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