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Vacation Rentals in Shelter Island, New York

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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

 

Sparkling Pointe

Sparlking Pointe is more or less an outlier in LI's wine region. They only do one thing - the bubbly. Like many of LI's wineries, it certainly is...read more

 

One Woman Wines & Vineyard

By far our FAVORITE stop of the day. We had a great time talking to the people behind the counter. Can't wait to enjoy the wines we brought home from here.read more

 

Raphael Vineyard and Winery

Raphael Winery is hands down my favorite on the North Fork! We have gone there several times and we are never disappointed. The wines are delicious and it...read more

 

Cross Sound Ferry

Took the Cross Sound Ferry from New London, Ct to Orient Point, NY and decided to spend the trip in the bar/Cross Sound Deli on the ferry. The bartender,...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

 

Croteaux Vineyards

It's like walking onto the set of a movie. Suddenly I feel like I'm in a scene from under the tuscan sun and it's pretty amazing. They don't allow the mega...read more

 

Mattebella Vineyards

Yay for you for finding this review! It means you will know about a hidden gem on the North Fork - Mattebella! Have been going here for years (after...read more

 

Sannino's Bella Vita Vineyard

This was the second stop on our wine tour and we opted to have the Vine to Wine tour, which includes about 5 tastings and taught us all about the wine...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

 

Wolffer Estate

Beautiful vineyard, romantic tasting room. Overlooking vineyard outdoor porch for relaxing afternoon for tasting wines. It was Friday afternoon, winery was...read more

 

Pindar Vineyards

As someone who has been a wine enthusiast for years, I can confidently say that this was the worst wine I have ever had in my life. Worse than Barefoot, or...read more

 

Duck Walk Vineyards

The place is clean which is what made the review 3 stars. I wish I could even rate it a 2.5. They didn't have our reservation written down, but accommodated...read more

 

Kontokosta Winery

This winery is absolutely breathtaking. After going up a long driveway, you'll see their red barn door. The two level tasting room is very sleek and...read more

 

Orient Beach State Park

This is a cool state park/beach hybrid, with playgrounds and picnic areas. I came here with my family Fourth of July Weekend and it wasn't even crowded. The...read more

 

The Lenz Winery

We were here for about an hour while on a wine tour that hit up 3 vineyards. We arrived late so we didn't get to do anything other than sample 4 wines in...read more

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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 /wk
 
 
 
 
 

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A Zen-like Retreat in North Haven 4 to 7 Bedrooms
Shelter Island House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $5,357 /nt
    $100,000 /mth
 
 
 
 
 

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Elegant Designer Hamptons Retreat in Sag Harbor/ North Haven
Shelter Island Estate Rental Picture
  • bedrooms 7
  • rental type Estate
  • owner badgeowner badge
  • sleeps 14
  • baths 7
  • rates (USD) $1,700 - $3,214 /nt
    $10,000 - $14,000 /wk
    $45,000 - $90,000 /mth
 
 
 
 
 

8 reviews write a review

Luxury,Quiet,Pool,Spotless, Beaches,Main+Guest House, sleeps 12 +
Shelter Island Estate Rental Picture
  • bedrooms 6
  • rental type Estate
  • owner badgeowner badge
  • sleeps 14
  • baths 7
  • rates (USD) $450 - $1,100 /nt
    $4,995 - $6,995 /wk
 
 
 
 
 

7 reviews write a review

Shelter Island Renovated Barn Hideaway Pool • Water Access • Hamptons
Shelter Island Barn Rental Picture
  • bedrooms 2
  • rental type Barn
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $12,500 - $20,000 /mth
 
 
 
 
 

2 reviews write a review

Beautiful, Secluded, Waterfront with Wrap-around Porch and Roof Deck
Shelter Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 9
  • baths 3
  • rates (USD) $500 - $1,000 /nt
    $6,300 /wk
    $24,000 - $28,933 /mth
 
 
 
 
 

1 reviews write a review

Spacious Vacation Home On 2 Private Acres With Community Tennis
Shelter Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $5,000 - $13,000 /wk
    $14,000 - $42,000 /mth
 
 
 
 
 

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Peaceful Shelter Island Home w/ Pool, Hot Tub and Walk to Beach
Shelter Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD)
 
 
 
 
 

3 reviews write a review

Gorgeous Home in Beach Community with Heated Saltwater Pool
Shelter Island House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 3
  • rates (USD) $5,600 - $5,950 /wk
    $24,800 /mth
 
 
 
 
 

2 reviews write a review

4BR 2.5 Bath spacious home with private beach access
Shelter Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $1,143 - $1,429 /nt
 
 
 
 
 

2 reviews write a review

Escape, Forget, Recharge To This Gorgeous Ultra-Private Compound Featuring Histo
Shelter Island House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 12
  • baths 5
  • rates (USD) $2,143 /nt
 
 
 
 
 

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