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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

 

One Woman Wines & Vineyard

Had a great experience with my friend here last week! This is the third winery I've visited in the North Fork and each experience has been so different but...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

 

Sparkling Pointe

Not at all intimate. Think overly giddy "brides maids showing up in club wear & arriving in white limos" argh. Or an enterage of "Housewives of some NYC...read more

 

Wolffer Estate Vineyard

You may find yourself feeling unwelcome. If it wasn't for how stunning this place is, I would have only given it 3 stars. The service was unfortunately...read more

 

Cross Sound Ferry

The good: Took the ferry just last week to and from Long Island. Both times I showed up early, early meaning, a couple of hours on the going trip and an...read more

 

Sannino's Bella Vita Vineyard

Small winery, not crowded, it gives intimate feel. The staffs are very friendly, personable & knowledge. I had a great time chatting with them. The grape...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

 

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

 

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

 

Kontokosta Winery

The place is popular. The staffs look super busy, jumping from one group to another. The wine is good, but nothing to die for. I come here for one reason...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

 

Pindar Vineyards

Stop here yesterday with my girlfriends after a long day exploring the north fork. I thought at first we were at the wrong place... the outside of the...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

 

Duck Walk Vineyards

This was stop #2 out of 3 for our bus tour of the LI vineyards. The facility is a nice looking space with a beautiful back area to hang out and basque in...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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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) $1,000 - $4,000 /nt
    $10,000 - $20,000 /wk
    $68,000 - $75,000 /mth
 
 
 
 
 

9 reviews write a review

Sheltered And Secluded; Pet Friendly
Shelter Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $400 - $575 /nt
    $2,700 - $3,850 /wk
    $10,800 - $15,500 /mth
 
 
 
 
 

2 reviews write a review

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
 
 
 
 
 

1 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

Brand New Exclusive Designer Home- 6 Ensuite Beds, Salt Water Pool, Media Room
Shelter Island House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $5,000 /nt
    $20,000 /wk
    $90,000 /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

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

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 /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 - $6,000 /wk
    $14,000 - $20,000 /mth
 
 
 
 
 

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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) $1,429 /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

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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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)
 
 
 
 
 

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