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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.

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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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