Shelter Island Vacation Rentals, Homes, & More

5 Rentals

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Arial View of Secluded Landscape
1 / 16

Shelter Island Home
4 Bedrooms / 3.5 Bathrooms / Sleeps 10

“ Excellent ”1 Review

from

$350

/ night

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Bedrooms:4
Bathrooms:3.5
Sleeps:10
Type:Home
Per night:$350 - $729
Per week:$2,450 - $5,100
Pets allowed:Yes
Internet:Yes

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, ...

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Perfect Sanctuary

“ Excellent ”
July 4, 2012
What an unexpected and delightful surprise this ever commodious abode turned out to be. Besides the large and welcome free-flowing dining / living / kitchen arrangement, There seemed to be an endless supply of intimate nooks that could accommodate groupings of two or four, as well as the most impressive and appealing screened in porch and dining area . The landscape of scattered gardens (including an herb garden) is sweet, with outdoor entertainment patios and several great expansive lawns, very pet friendly . We really enjoyed the outdoor grill. A couple of bicycles available , made quick trips to the picturesque and secluded beach something to repeat often. The beds were comfortable, the bedrooms spacious, and the many baths with dual entrances made the house easy to share. We loved it and hope to return!!!
Christine Cornell, Weehawken N.J. USA

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77' Wrap around porch 20' x 40' In Ground Pool
1 / 31

Shelter Island Home
4 Bedrooms / 4 Bathrooms / Sleeps 10

“ Excellent ”9 Reviews

from

$400

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$400 - $795
Per week:$2,500 - $6,950
Pets allowed:Yes
Internet:Yes

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,...

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Wonderful Family Vacation

“ Excellent ”
October 2, 2011
We stayed at this amazing house from Sep 10-17 and had the best time (we = two couples and two toddlers). The house was perfect. Great location with all the amenities you can imagine inside and outside the house (pool, large back yard, outdoors storage for bikes, grills, 4 bedrooms (one of them a loft), the best kitchen, nice entertainment room, etc.The house was also just 2 minutes away from a very nice beach, totally quiet, literally across the street. The owner was very easy to deal with and everything was done very professionally. We had a small issue with the fridge and called and he responded right away. Problem solved in 5 minutes.There were really no cons. Maybe the fact that you have to bring your own garbage to the local recycling dump but that was not a big deal because we knew about it from all the information that the owner gave us.We would love to come back next year.
Bernt, NYC

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Shelter Island New York Vacation Rentals - Cottage
1 / 20

Shelter Island Cottage
2 Bedrooms / 1.5 Bathrooms / Sleeps 6

“ Excellent ”9 Reviews

from

$325

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:6
Type:Cottage
Per night:$325 - $495
Per week:$2,150 - $3,875
Pets allowed:Yes
Internet:Yes

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...

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Wonderful Surprise - a Mini Retreat

“ Excellent ”
July 25, 2010
After many years spent summering on Block Island, it was time for a change. The Shelter Island Hideaway cottage was better than we could have imagined. In an easy trip from CT, we were enticed by the farms and vineyards of the North Fork - reminiscent of Provence with farm stands and fields of lavender and sunflowers. Once on Shelter Island, it is easy to relax and forget about everyday concerns. Reddings and Greeny's Markets provide a wide variety of quality specialty foods to bring back to the cottage. Once there, it is difficult to find reason to leave, except to walk to the nearby beach at sunset. The open sun room flanked by two lap pools brings the outdoors in and the sound of the fountain flowing into the nearby Koi pond provides the perfect soundtrack. If the mood strikes to become social or to head out for a meal, there are good choices to meet most tastes on the island, with the South Fork a brief ferry ride away. Shelter Island Hideaway was the perfect respite for my two teenagers daughter and myself - relaxing and inspiring in a charming, zen-like setting.
Nina, Fairfield, CT

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Shelter Island New York Vacation Rentals - Home
1 / 35

Shelter Island Home
3 Bedrooms / 3 Bathrooms / Sleeps 5

“ Excellent ”4 Reviews

from

$470

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:5
Type:Home
Per night:$470
Per week:$2,800 - $3,990
Pets allowed:No
Internet:Yes

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...

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Relax on Shelter Island

“ Excellent ”
September 20, 2013
Having spent 1 week at our daughter's house in Brooklyn and several hectic days in Manhattan, we relaxed for 1 week at this beautiful property less than 5 minutes drive to Wades beach. The property was very private with excellent views from the terracing, and was of a very high standard. Clearly the owner is very artistic and has immaculate taste. It was almost like living in an art gallery, although fully and tastefully equipped in all respects. We would have no hesitation in recommending this property to any discerning holiday maker looking for a relaxing vacation.
John Langley, Yorkshire UK

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Shelter Island New York Vacation Rentals - Home
1 / 11

Shelter Island Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:Yes
Internet:Yes

Looking for a great summer retreat? Restaurants, antiquing, wineries, biking, canoeing, tennis, golf and of course the beach are all yours to be had at this charming east end gem on laid back Shelter Island. This renovated Country Cape is nestled on a spacious and lush ¾...

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The Great Escape!

“ Excellent ”
August 11, 2011
My husband and I rented this house for a week with another couple and had the most relaxing time. We both brought our babies and dogs along and found the property perfect for both. (Of course you have to be mindful of the pool and stairs etc.) The back yard is quite big and the pool is perfect for those hot summer days. Very quiet! And even on the hottest days it seemed cool. Plenty of shade. A few nice restaurants in the town and of course a short ferry ride from Sag Harbour. We will definitely be returning next summer!
Jennifer Taubenfeld, New York City

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