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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

My friend and I did a tasting at a local vineyard, and having some time left, we decided to stop by Sparkling Pointe. When we walked in, we were greeted...read more

 

One Woman Wines & Vineyard

This vineyard is one of those vineyards that you must stop at on the North Fork wine trail. I like to plan to visit this vineyard on Saturday nights in the...read more

 

Mattebella Vineyards

We stopped here to celebrate after my fiance proposed to me at Lavender by the Bay in East Marion last weekend. This was our last wine tasting stop of the...read more

 

Croteaux Vineyards

This was my first foray into LI vineyard wine tasting and this was a great first stop. They don't allow commercial buses to drop off to the overall vibe is...read more

 

Cross Sound Ferry

I live in Boston but travel on Long Island for work purposes. Sometimes it's a pain in the ass to travel by car from the most Eastern parts of the Island,...read more

 

Sannino's Bella Vita Vineyard

Was there on 7/13/14 for the tour. Excellent and very informative. We were running a few minutes late due to traffic on RTE 25, called up, and they actually...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

 

Wolffer Estate Vineyard

This is probably one of the best vineyards in the northeast. It rivals to many of which are in Napa. The European style grapes grown in the US should...read more

 

Kontokosta Winery

As many Yelpers have mentioned in their reviews, the views here are what really set this spot apart from other wineries. You've got an amazing overlook of...read more

 

Raphael Vineyard and Winery

Raphael Vineyards is a beautiful location to visit. The inside is grand with huge chandeliers and a wonderful circle bar in the middle as the focal point....read more

 

Wolffer Estate

My experience at Wolffer Estate was hands down my top experience at a winery. I've been to a handful in the North fork and a couple in upstate New York but...read more

 

Orient Beach State Park

For what this is, this is a phenomenal beach. And what it is: a quiet pristine beach that family friendly and has beautiful scenery. We enjoyed an entire...read more

 

Pindar Vineyards

I'm giving this place 4 stars for two big reasons: 1. They allow dogs 2. They allow you to bring your own food so long as you eat at the covered patio way...read more

 

The Winemaker Studio

One of those "hidden gems" in the North Fork. Each time I get to stop by, I am thoroughly impressed. They offer wines from various winemakers and also...read more

 

The Lenz Winery

This is a classic Long Island winery that offers something truly unique to the area - some world class wines! Our group was greeted enthusiastically, and...read more

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Private Waterfront & Great Sunsets
Shelter Island Cottage Rental Picture
  • bedrooms 4
  • community
  • rental type Cottage
  • sleeps 8
  • baths 2
  • rates (USD) $1,650 - $3,150 /wk
 
 
 
 
 

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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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Sheltered And Secluded; Pet Friendly
Shelter Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $350 - $550 /nt
    $2,500 - $4,000 /wk
    $10,000 - $15,000 /mth
 
 
 
 
 

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Elegant Designer Hamptons Retreat in Sag Harbor/ North Haven- steps to Bay Beach
Shelter Island Estate Rental Picture
  • bedrooms 7
  • rental type Estate
  • owner badgeowner badge
  • sleeps 14
  • baths 7
  • rates (USD) $1,500 - $4,000 /nt
    $10,000 - $20,000 /wk
    $45,000 - $72,000 /mth
 
 
 
 
 

9 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
    $22,000 - $28,933 /mth
 
 
 
 
 

1 reviews write a review

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) $5,250 - $10,500 /wk
 
 
 
 
 

5 reviews write a review

Brand New Exclusive Designer Home- 6 Ensuite Beds, Salt Water Pool, Media Room
Shelter Island House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $2,500 /nt
    $65,000 /mth
 
 
 
 
 

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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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NEW: WALK TO WATER, Secret Garden English Style newly renovated home
Shelter Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 7
  • baths 3
  • rates (USD) $1,000 /nt
 
 
 
 
 

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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 - $898 /nt
 
 
 
 
 

7 reviews write a review

4BR 2.5 Bath Avail week 1 Aug only
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

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

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

A Zen-like Retreat in North Haven 4 to 7 Bedrooms & 7 Bathrooms
Shelter Island House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $3,571 /nt
    $25,000 /wk
    $80,000 - $100,000 /mth
 
 
 
 
 

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Beautiful, Waterfront Home With Dock And Heated Saltwater Gunite Pool!
Shelter Island House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $3,500 - $5,950 /wk
    $12,000 - $22,500 /mth
 
 
 
 
 

9 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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