Shelter Island Vacation Rentals - HomeToGo base64Hash Shelter Island Vacation Rentals - HomeToGo

Shelter Island Vacation Rentals

Find 1,005 available offers from 3 partners
Anytime
1 guest
Anytime
1 guest

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Apartment
    • House
    • Bed and breakfast

  • Distance to center

    • 1 km
    • 2 km
    • 5 km

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • WiFi
    • Kitchen
    • Air conditioning
    • TV
    • Washing machine
    • Parking
    • Microwave
    • Dishwasher
    • Balcony/patio
    • Yard
    • Jacuzzi
    • Fireplace
    • Sauna
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Recommended vacation rentals in Shelter Island

Find your perfect vacation rental in Shelter Island from just $158 per night!

House Shelter Island
House ∙ 12 guests ∙ 6 bedrooms

House

Shelter Island, Suffolk County, New York, United States
from $1,067
per night
Outstanding(27 ratings)
from $1,067
per night
View deal
House Shelter Island
House ∙ 7 guests ∙ 4 bedrooms

House

Shelter Island, Suffolk County, New York, United States
from $598
per night
Outstanding(22 ratings)
from $598
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

279 m² House

Shelter Island, Suffolk County, New York, United States
from $430
per night
Outstanding(22 ratings)
from $430
per night
View deal
House Shelter Island
House ∙ 12 guests ∙ 6 bedrooms

437 m² House

Shelter Island, Suffolk County, New York, United States
from $1,079
per night
Outstanding(21 ratings)
from $1,079
per night
View deal
Cottage Shelter Island
Cottage ∙ 4 guests ∙ 3 bedrooms

84 m² Cottage

Shelter Island, Suffolk County, New York, United States
from $472
per night
Outstanding(43 ratings)
from $472
per night
View deal
House Shelter Island
House ∙ 8 guests ∙ 5 bedrooms

204 m² House

Shelter Island, Suffolk County, New York, United States
from $624
per night
Excellent(20 ratings)
from $624
per night
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

325 m² House

Shelter Island, Suffolk County, New York, United States
from $449
per night
Outstanding(27 ratings)
from $449
per night
View deal
House Shelter Island
House ∙ 4 guests ∙ 2 bedrooms

93 m² House

Shelter Island, Suffolk County, New York, United States
from $566
per night
Very good(11 ratings)
from $566
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

74 m² House

Shelter Island, Suffolk County, New York, United States
from $306
per night
Outstanding(20 ratings)
from $306
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

130 m² House

Shelter Island, Suffolk County, New York, United States
from $258
per night
Outstanding(47 ratings)
from $258
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

House

Shelter Island, Suffolk County, New York, United States
from $747
per night
Outstanding(12 ratings)
from $747
per night
View deal
Cottage Shelter Island
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage

Shelter Island, Suffolk County, New York, United States
from $1,028
per night
Outstanding(116 ratings)
from $1,028
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

112 m² House

Shelter Island, Suffolk County, New York, United States
from $530
per night
Outstanding(4 ratings)
from $530
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

House

Shelter Island, Suffolk County, New York, United States
from $478
per night
Outstanding(48 ratings)
from $478
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 5 bedrooms

223 m² House

Shelter Island, Suffolk County, New York, United States
from $1,139
per night
Outstanding(4 ratings)
from $1,139
per night
View deal

Apartments with a balcony or patio

Cottage Shelter Island
from $158 per night
Cottage ∙ 3 guests ∙ 2 bedrooms
5.0
Outstanding(1 rating)
Shelter Island, Suffolk County, New York, United States
Balcony/Patio
View deal
House Shelter Island
from $346 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding(40 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony/Patio
View deal
Apartment Shelter Island
from $533 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding(68 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony/Patio
View deal
See all offers

Vacation homes and cottages with a garden

House Shelter Island
from $292 per night
House ∙ 11 guests ∙ 5 bedrooms
5.0
Outstanding(58 ratings)
Shelter Island, Suffolk County, New York, United States
Yard
View deal
House Shelter Island
from $1,172 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(42 ratings)
Shelter Island, Suffolk County, New York, United States
Yard
View deal
House Shelter Island
from $806 per night
House ∙ 10 guests ∙ 7 bedrooms
4.8
Outstanding(60 ratings)
Shelter Island, Suffolk County, New York, United States
Yard
View deal
See all offers

Vacation homes with fishing spots nearby

House Shelter Island
from $360 per night
House ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding(13 ratings)
Shelter Island, Suffolk County, New York, United States
Fishing
View deal
Cottage Shelter Island
from $270 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(31 ratings)
Shelter Island, Suffolk County, New York, United States
Fishing
View deal
Farmhouse Shelter Island
from $1,012 per night
Farmhouse ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(3 ratings)
Shelter Island, Suffolk County, New York, United States
Fishing
View deal
See all offers

Best Vacation Home Deals in Shelter Island

Save up to 48%

Apartment Shelter Island
Dec 21 - Dec 28
-48%
$986
$516 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(61 ratings)
Shelter Island, Suffolk County, New York, United States
View deal

Find the ideal vacation home from $158 per night by searching through the 1,005 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.

Budget-friendly Rentals in Shelter Island

Find Fantastic yet Inexpensive Rentals

House Shelter Island
from $455 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(8 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
House Shelter Island
from $876 per night
House ∙ 6 guests ∙ 4 bedrooms
5.0
Outstanding(108 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
House Shelter Island
from $476 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(103 ratings)
Shelter Island, Suffolk County, New York, United States
View deal

Top-Rated Offers and Accommodations in Shelter Island

Book Vacation Rentals with the Highest User Rating

House Shelter Island
from $1,091 per night
House ∙ 10 guests ∙ 4 bedrooms
4.5
Excellent(49 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
Apartment Shelter Island
from $351 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(31 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
House Shelter Island
from $1,745 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(28 ratings)
Shelter Island, Suffolk County, New York, United States
View deal

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Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Shelter Island

  • Pool (457)
  • WiFi (970)
  • Kitchen (744)
  • Pet-friendly (297)
  • Air conditioning (941)
  • TV (852)
  • Washing machine (388)
  • Parking (41)
  • Microwave (632)
  • Dishwasher (420)
  • Balcony/patio (523)
  • Grill (390)

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 $1,126 a night. If you would also like to be close to the water, more than half 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 1,005 rentals
💳 Possible discounts up to 48%
🌙 Nightly prices starting at $158
⭐ Popular amenities Pool, Internet and Kitchen
🐾 Pet friendly homes 297 homes
🏊 Vacation rentals with pools 458 homes

Frequently Asked Questions

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

At the moment, there are 1,005 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 297 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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