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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Check out more areas which feature homes, villas, cabins, cottages, or condos.
Shelter Island things to do
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
Shelter Island Kayak Tours
Jay, your guide, operates out of an unassuming sleepy little shack adjacent to a restaurant called Planet Bliss. He's been written about in so many...read more
Sparkling Pointe
We really enjoyed our visit to Sparkling Pointe. The space is modern, clean, elegant - a bit of Rio or upscale Carribean in the middle of the north fork....read more
Wolffer Estate
If you're looking for a relaxing vino escape while in the Hamptons, head to Wölffer Estate Vineyards, located in Bridgehampton in the South Fork of Suffolk...read more
Cedar Point County Park
I really hate to camp. But the several times I've been here to visit friends who are camping at Cedar Point, I have to say I was very amazed that such a...read more
Wolffer Estate Vineyard
There are only 3 wineries on the south fork and this is #1 winery out of the 3. The service is top-notch. My favorite is the rose table wine. I did the...read more
Duck Walk Vineyards
This is a great winery for a tasting. I've been to both Duck Walk Vineyards and they both have nice tasting rooms. It's true, when it's busy, it's...read more
One Woman Wines & Vineyard
We adored this rustic barn for a tasting room. The day we tasted, there was an event including gratis warm food (the ratatouille was absolutely amazing),...read more
Pindar Vineyards
First stop on a recent wine tasting tour. - laid back & cozy vibe - friendly staff - large selection of tastings - i enjoyed the winter white & reisling...read more
Duckwalk Vineyards
I love Duckwalk for what it is; convenient to my grandparents home in Watermill, inexpensive wine tastings (that never seem to stop) and a lovely outdoor...read more
Orient Beach State Park
I stood at the HP LaserJet patiently awaiting my printout to emerge from the seemingly endless queue at work. I flipped through what'd already made it...read more
Osprey's Dominion Vineyards
I just had a 2008 Oak-barrel Chardonnay from Osprey's Dominion, which I bought at a local liquor store for under 10 dollars. That's kind of unheard of,...read more
The Lenz Winery
This might have been our favorite winery on the North Fork. The tasting room is in a lovely potato barn from the 1920's, with high ceilings and good light....read more
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10% off = $7,200 per month
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$3,000
- $4,500
/wk
$8,000 - $13,000 /mth
- bedrooms 4
- community Shorewood
- rental type House
- sleeps 10
- baths 3
- rates (USD)
$1,495
- $1,495
/wk
$5,000 - $5,000 /mth
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$3,000
- $3,000
/wk






