Vacation Rentals in Shelter Island, New York
Shelter Island, New York Vacation Rentals and Tourism
Shelter Island, NY, is all its name implies – a tiny island sheltered between Long Island’s forks, the island serves as a pleasant respite and vacation destination. The ideal way to relax here is in Shelter Island vacation rentals, where you and your family will enjoy privacy and plenty of space for reading, relaxing and planning the day’s events. When you can have all the space and comfort, a full kitchen and outdoor space in Shelter Island cottages, why even consider hotels?
Stay in a waterfront Shelter Island vacation house, and enjoy exploring the coves, swimming and boating. A large part of the island is set aside as a nature preserve, and makes for great wildlife viewing and birding. Stroll through Shelter Island Heights’ antique shops and take a break for coffee or dinner; play golf or tennis; take in a free concert – you’ll love the laid back atmosphere. For more dining and shopping, take the ferry to Greenport or to Sag Harbor and the Hamptons for more sights, restaurants and shops on Long Island.
Just five miles from Sag Harbor, Shelter Island, NY, feels worlds away from ordinary. Plan your getaway and book your Shelter Island beach rental or vacation house today!
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Shelter Island things to do
Shelter Island Kayak Tours
Our guide Tom was great and gave us a wonderful tour around the east side of the island. We saw some Ospreys and also landed at Taylor's Island which has a...read more
Gardiner's Bay Country Club Inc
Very nice country club based on my brief visit there yesterday. The members were all friendly. It does seem that they take their dress code seriously, as I...read more
Sparkling Pointe
Sparkling Pointe...the name alone draws you in, the French flag flying out front seals the deal. Of all the vineyards on Long Island, Sparkling Pointe...read more
One Woman Wines & Vineyard
Love going to this winery, here is the reason why: It is a family run vineyard with a nice selection of wines, mainly whites, one delicious Merlot, from...read more
Wolffer Estate Vineyard
This was my first wine tasting at a vineyard and it was the perfect outing for a not so great beach day. I was told that they are "different from other...read more
Cedar Point County Park
Camping ranked very high on the list of things I had absolutely no interest in doing, ever. Here's why: - Setup and break down is too much damn work....read more
Cross Sound Ferry
We took this ferry on the way back from Acadia National Park and made it just in time. The trick when coming from that far away is to time the arrival....read more
Croteaux Vineyards
My first time here.. I was impressed! It's a romantic winery.. The ambiance is very much relaxing.. On weekdays very quiet.. Just let the time pass while...read more
Orient Beach State Park
A great park and beach that has miles and miles of places to walk. Apparently not very many people know about it because it never seems to be crowded,...read more
Raphael Vineyard and Winery
This winery is my favorite on the North Fork of the island. Not only is the wine delicious, but the winery itself really has that 'wow' factor. I first...read more
The Lenz Winery
OMG, would you folks grow a pair? Think about what happens at a vineyard, They are trying to run a business on the east end of Long Island. Its not all Rose...read more
Mattebella Vineyards
Vineyard We were tooling about the east end and looking for open vineyards - not an easy feat in the winter, and we drove past Mattebella, which had an...read more
Wolffer Estate
I stopped in here as we were leaving the Hamptons to pick up some wine for my father-in-law's birthday. The staff was very helpful and friendly - things...read more
The Winemaker Studio
The Winemaker Studio occupies the space of what was once The Tasting Room. I never had a chance to visit that place before it closed, but I hear it was a...read more
Duck Walk Vineyards
If you want a rowdy college party - go to their north fork location. Horrible, loud, bar is jammed and the place looks like they are selling kmart wine. ....read more
- bedrooms 4
- community
- rental type Cottage
- sleeps 8
- baths 2
- rates (USD)
$1,550
- $2,500
/wk
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$3,000
- $3,000
/wk
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