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Shelter Island Vacation Rentals

Find 767 available offers from 2 partners
Shelter Island
Anytime
Guests
Shelter Island
Anytime
Guests

Popular Filters to find the Perfect Rental in Shelter Island

2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
House
Internet

Vacation rentals with Wi-Fi

Cottage  Shelter Island
Sept 2 - Sept 9
-9%
$716
$654 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Children-Friendly Cottage with Patio & BBQ | Nature View | Dogs Allowed

5.0
Outstanding (75 ratings)
Shelter Island, Suffolk County, New York, United States
Internet
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Cottage  Shelter Island
Sept 2 - Sept 9
-9%
$744
$679 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Beautiful Cottage with Barbeque, Patio & Yard | Dogs Allowed

5.0
Outstanding (104 ratings)
Shelter Island, Suffolk County, New York, United States
Internet
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House  Shelter Island
Jul 27 - Aug 3
$1,526 per night
House ∙ 10 guests ∙ 3 bedrooms

House with BBQ, Garden & Terrace | Nature View

Shelter Island, Suffolk County, New York, United States
Internet
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Best vacation rentals with a balcony

House  Shelter Island
Aug 3 - Aug 10
$1,397 per night
House ∙ 6 guests ∙ 3 bedrooms

House with Garden, Heated Pool & Terrace | Water View

Shelter Island, Suffolk County, New York, United States
Balcony
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Bed and breakfast  Shelter Island
Sept 27 - Oct 4
-56%
$1,406
$612 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & Breakfast with Terrace, Pool & Garden | Next to the Beach | Suitable for Remote Work

Shelter Island, Suffolk County, New York, United States
Free cancellation
Balcony
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Bed and breakfast  Shelter Island
Oct 5 - Oct 12
-44%
$1,283
$718 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with Patio, Yard & Private Pool

Shelter Island, Suffolk County, New York, United States
Free cancellation
Balcony
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Vacation rentals with a fireplace

House  Shelter Island
from $602 per night
House ∙ 30 guests ∙ 3 bedrooms

Child-Friendly Vacation Home with Garden, Terrace & BBQ | Good for Workation | Pet-Friendly

Shelter Island, Suffolk County, New York, United States
Fireplace
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House  Shelter Island
from $1,334 per night
House ∙ 9 guests ∙ 4 bedrooms

Vacation Home with Yard, Terrace & Private Pool | Nature View

5.0
Outstanding (28 ratings)
Shelter Island, Suffolk County, New York, United States
Fireplace
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House  Shelter Island
from $1,869 per night
House ∙ 8 guests ∙ 4 bedrooms

Children-Friendly Vacation Home with Garden, Barbecue & Patio | City View | Good for Workation

5.0
Outstanding (12 ratings)
Shelter Island, Suffolk County, New York, United States
Fireplace
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Best Vacation Home Deals in Shelter Island

Save up to 4%

Cottage Shelter Island
Sept 2 - Sept 9
-4%
$632
$604 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Family-Oriented Cottage with Yard, Patio & Grill | Pets Are Welcome

5.0
Outstanding (30 ratings)
Shelter Island, Suffolk County, New York, United States
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Find the ideal vacation home from $185 per night by searching through the 767 properties available in Shelter Island. HomeToGo instantly highlights the best offers by comparing all of the available vacation rentals in Shelter Island from 3 different providers.

Recommended Vacation Rentals in Shelter Island

Find your perfect vacation rental in Shelter Island: from $185 per night

House Shelter Island
Jul 27 - Aug 3
$1,548 per night
House ∙ 8 guests ∙ 3 bedrooms

House with Private Pool, Patio & Garden

5.0
Outstanding (4 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $663 per night
House ∙ 10 guests ∙ 3 bedrooms

Child-Friendly Spacious Vacation Home with Terrace, Private Pool & Yard

Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $1,486 per night
House ∙ 12 guests ∙ 6 bedrooms

Children-Friendly Beautiful Vacation Home with Yard & BBQ | Nature View | Good for Workation | Pet-Friendly

5.0
Outstanding (14 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $607 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home for Family Getaway with Garden, Patio & Private Pool | Nature View

4.9
Outstanding (49 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $235 per night
House ∙ 6 guests ∙ 3 bedrooms

House with BBQ & Yard | Nature View

4.9
Outstanding (41 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $846 per night
House ∙ 10 guests ∙ 4 bedrooms

Children-Friendly Nice House with Patio, BBQ & Yard

5.0
Outstanding (34 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $1,137 per night
House ∙ 8 guests ∙ 4 bedrooms

Children-Friendly Wonderful House with Patio, Garden & Private Pool | Nature View | Suitable for Remote Work | Dogs Allowed

5.0
Outstanding (32 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $1,021 per night
House ∙ 12 guests ∙ 5 bedrooms

Family-Oriented Vacation Home with Patio, Yard & Barbecue | Nature View

4.7
Excellent (20 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $324 per night
House ∙ 6 guests ∙ 3 bedrooms

House | Pets Are Welcome

Shelter Island, Suffolk County, New York, United States
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Budget-friendly Rentals in Shelter Island

Find Fantastic yet Inexpensive Rentals

House Shelter Island
from $503 per night
House ∙ 6 guests ∙ 3 bedrooms

Family-Oriented Ample House with Yard, Barbeque & Terrace | Nature View

4.9
Outstanding (39 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $1,478 per night
House ∙ 6 guests ∙ 3 bedrooms

Family-Oriented Pleasant Vacation Home with Yard, Patio & Grill | City View | Perfect for Remote Work

5.0
Outstanding (8 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $925 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Garden, Patio & BBQ | Nature View

5.0
Outstanding (14 ratings)
Shelter Island, Suffolk County, New York, United States
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Top-Rated Offers and Accommodations in Shelter Island

Book Vacation Rentals with the Highest User Rating

Apartment Shelter Island
from $384 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Family-Oriented Beautiful Holiday Apartment with Garden | Suitable for Remote Work

5.0
Outstanding (20 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $382 per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home with Grill, Yard & Terrace

5.0
Outstanding (10 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
from $788 per night
House ∙ 10 guests ∙ 4 bedrooms

Family-Friendly House for Family Getaway with BBQ, Garden & Terrace | Good for Workation

4.9
Outstanding (8 ratings)
Shelter Island, Suffolk County, New York, United States
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Popular Rental Amenities in Shelter Island

  • Pool (402)
  • WiFi (753)
  • Kitchen (531)
  • Pet-friendly (160)
  • Air conditioning (720)
  • TV (666)
  • Washing machine (415)
  • Parking (27)
  • Microwave (448)
  • Dishwasher (421)
  • Balcony/patio (558)
  • Grill (407)

You will have a large selection of vacation rentals to choose from if you are looking for an accommodation offering a pool in Shelter Island. In addition, more hotel room offer a pool than aparthotel. Most of the hotel room with pools in Shelter Island accommodate 5 vacationers and have an average cost of $1,259 a night. If you would also like to be close to the water, many of the vacation rentals offering a pool are located within 2 kilometres of the waterfront.

Information about vacation rentals in Shelter Island

🏡 Vacation rentals available 767 rentals
💳 Possible discounts up to 17%
🌙 Nightly prices starting at $185
⭐ Popular amenities Pool, Internet and Kitchen
🐾 Pet friendly homes 161 homes
🏊 Vacation rentals with pools 403 homes

Frequently Asked Questions

What is the typical availability of vacation rentals in Shelter Island?

At the moment, there are 767 vacation homes from 3 different providers in Shelter Island.

What are the most popular vacation home amenities in Shelter Island?

When looking to book a vacation home in Shelter Island, the most requested amenities include Pool, Internet, and Kitchen.

Are there pet-friendly vacation rentals in Shelter Island?

Finding a vacation rental in Shelter Island that allows dogs is definitely possible, with 161 pet-friendly homes on offfer.

What's the best month to visit Shelter Island?

If you're looking for balmy weather, July and August are typically the hottest months in Shelter Island with temperatures around 26 °C. January and February in Shelter Island are the coldest, with -1 °C on average.

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