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Vacation Rentals in Shelter Island, New York

about Shelter Island

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

 

South Ferry Company

Gets done what needs to be done.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

 

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

 

Raphael

The service is good. A wine tasting was about half a glass (which I found out after ordering a glass and being disappointed). The building is large and has...read more

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DEAL!! Holly House-Summer Retreat w/Pool, Jacuzzi & Walk to Beach
Shelter Island House Rental Picture
  • House Rental Deals and Discounts 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
 
 
 
 
 

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Shelter Island Retreat- Private Beach /Tennis
Shelter Island House Rental Picture
  • bedrooms 4
  • community Shorewood
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $1,495 - $1,495 /wk
    $5,000 - $5,000 /mth
 
 
 
 
 

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Bush Rose - a Shelter Island Summer Home with pool
Shelter Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $3,000 - $3,000 /wk
 
 
 
 
 

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