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

Shelter Island Vacation Rentals

Find 729 available home rentals from 2 partners
Anytime
Guests
Anytime
Guests

  • Price per night

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

  • Accommodation types

    • Apartment
    • House
    • Bed and breakfast

  • Distance to center

    • 2 km
    • 5 km
    • Any

  • Rating

    • 4.5+
    • 4+

  • 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

Top 15 Recommended vacation rentals in Shelter Island

Find your perfect vacation rental in Shelter Island from just $350 per night!

House Shelter Island
House ∙ 10 guests ∙ 4 bedrooms

House

Shelter Island, Suffolk County, New York, United States
This house rental in Sag Harbor offers a private pool, jacuzzi, and spacious yard, perfect for family gatherings and pets.
from $1,065
per night
Outstanding(2 ratings)
from $1,065
per night
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

186 m² House

Shelter Island, Suffolk County, New York, United States
This waterfront house on Shelter Island features a pool, balcony, and yard, perfect for families seeking a memorable getaway.
from $796
per night
Outstanding(38 ratings)
from $796
per night
View deal
House Shelter Island
House ∙ 5 guests ∙ 4 bedrooms

232 m² House

Shelter Island, Suffolk County, New York, United States
This house rental on Shelter Island Heights offers a private heated pool, beach access, and family-friendly amenities for 5 guests.
from $859
per night
Outstanding(14 ratings)
from $859
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

167 m² House

Shelter Island, Suffolk County, New York, United States
This house rental on Shelter Island Heights features a private heated pool, yard, and family-friendly amenities for six guests.
from $914
per night
Outstanding(23 ratings)
from $914
per night
View deal
House Shelter Island
House ∙ 8 guests ∙ 3 bedrooms

225 m² House

Shelter Island, Suffolk County, New York, United States
This North Fork house rental accommodates eight guests with a private heated pool, yard, and family-friendly amenities for all.
from $723
per night
Outstanding(22 ratings)
from $723
per night
View deal
House Shelter Island
House ∙ 12 guests ∙ 5 bedrooms

437 m² House

Shelter Island, Suffolk County, New York, United States
This house rental on Shelter Island Heights features a fireplace, kitchen, yard, and balcony, accommodating up to 12 guests.
from $1,195
per night
Outstanding(23 ratings)
from $1,195
per night
View deal
Cabin Shelter Island
Cabin ∙ 4 guests ∙ 2 bedrooms

84 m² Cabin

Shelter Island, Suffolk County, New York, United States
This cozy cottage on Shelter Island features a kitchen, a yard, and parking, perfect for a family getaway for four.
from $515
per night
Outstanding(43 ratings)
from $515
per night
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

House

Shelter Island, Suffolk County, New York, United States
This Shelter Island house rental features a private heated pool, a spacious yard, and a balcony, perfect for family gatherings.
from $1,206
per night
Outstanding(49 ratings)
from $1,206
per night
View deal
House Shelter Island
House ∙ 10 guests ∙ 4 bedrooms

House

Shelter Island, Suffolk County, New York, United States
This house rental on Shelter Island Heights features a private pool, beach access, and a spacious yard, perfect for families and pets.
from $737
per night
Outstanding(26 ratings)
from $737
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

155 m² House

Shelter Island, Suffolk County, New York, United States
This house rental in Shelter Island Heights features a kitchen, fireplace, yard, and parking, perfect for families and pets.
from $859
per night
Outstanding(103 ratings)
from $859
per night
View deal
House Shelter Island
House ∙ 9 guests ∙ 3 bedrooms

House

Shelter Island, Suffolk County, New York, United States
A pet-friendly house rental on Shelter Island Heights features a private pool, fireplace, and yard, perfect for family getaways.
from $1,023
per night
Outstanding(26 ratings)
from $1,023
per night
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

House

Shelter Island, Suffolk County, New York, United States
This North Fork house rental features waterfront access, a Jacuzzi, and a balcony, perfect for family gatherings of up to 8.
from $1,419
per night
Outstanding(202 ratings)
from $1,419
per night
View deal
House Shelter Island
House ∙ 10 guests ∙ 5 bedrooms

297 m² House

Shelter Island, Suffolk County, New York, United States
This North Fork house rental features a private heated pool, a spacious yard, and amenities for a memorable family getaway.
from $1,111
per night
Outstanding(89 ratings)
from $1,111
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

223 m² House

Shelter Island, Suffolk County, New York, United States
This waterfront house on Shelter Island Heights offers a yard, kitchen, fireplace, and parking for a perfect family getaway.
from $861
per night
Outstanding(6 ratings)
from $861
per night
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

228 m² House

Shelter Island, Suffolk County, New York, United States
This spacious house rental on Shelter Island features a private heated pool, yard, and balcony, perfect for family vacations.
from $1,161
per night
Outstanding(43 ratings)
from $1,161
per night
View deal

Vacation rentals and apartments with air conditioning

House Shelter Island
from $669 per night
House ∙ 6 guests ∙ 3 bedrooms

170 m² House

5.0
Outstanding(68 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
View deal
House Shelter Island
from $1,856 per night
House ∙ 8 guests ∙ 4 bedrooms

House

5.0
Outstanding(16 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
View deal
House Shelter Island
from $1,786 per night
House ∙ 13 guests ∙ 7 bedrooms

465 m² House

5.0
Outstanding(117 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
View deal
See all offers

Best vacation rentals with a balcony

House Shelter Island
from $1,461 per night
House ∙ 10 guests ∙ 5 bedrooms

251 m² House

5.0
Outstanding(51 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
View deal
House Shelter Island
from $507 per night
House ∙ 5 guests ∙ 3 bedrooms

149 m² House

5.0
Outstanding(62 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
View deal
House Shelter Island
from $2,253 per night
House ∙ 10 guests ∙ 5 bedrooms

282 m² House

5.0
Outstanding(48 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
View deal
See all offers

Vacation rentals with a fireplace

Cabin Shelter Island
from $414 per night
Cabin ∙ 4 guests ∙ 1 bedroom

84 m² Cabin

5.0
Outstanding(6 ratings)
Shelter Island, Suffolk County, New York, United States
Fireplace
View deal
House Shelter Island
from $711 per night
House ∙ 6 guests ∙ 3 bedrooms

House

5.0
Outstanding(22 ratings)
Shelter Island, Suffolk County, New York, United States
Fireplace
View deal
House Shelter Island
from $870 per night
House ∙ 5 guests ∙ 3 bedrooms

158 m² House

5.0
Outstanding(66 ratings)
Shelter Island, Suffolk County, New York, United States
Fireplace
View deal
See all offers

Budget-friendly Rentals in Shelter Island

Find Fantastic yet Inexpensive Rentals

House Shelter Island
from $726 per night
House ∙ 8 guests ∙ 4 bedrooms

260 m² House

4.9
Outstanding(32 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
House Shelter Island
from $1,424 per night
House ∙ 7 guests ∙ 4 bedrooms

186 m² House

5.0
Outstanding(16 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
Cabin Shelter Island
from $957 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cabin

5.0
Outstanding(124 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

Cabin Shelter Island
from $186 per night
Cabin ∙ 4 guests ∙ 2 bedrooms

79 m² Cabin

4.9
Outstanding(131 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
Apartment Shelter Island
from $445 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

125 m² Apartment

5.0
Outstanding(70 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
House Shelter Island
from $940 per night
House ∙ 6 guests ∙ 3 bedrooms

195 m² House

4.8
Outstanding(64 ratings)
Shelter Island, Suffolk County, New York, United States
View deal

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

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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 (384)
  • WiFi (690)
  • Kitchen (487)
  • Pet-friendly (220)
  • Air conditioning (668)
  • TV (615)
  • Washing machine (373)
  • Parking (25)
  • Microwave (417)
  • Dishwasher (382)
  • Balcony/patio (501)
  • Grill (391)

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 3 vacationers and have an average cost of $1,532 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 729 rentals
🌙 Nightly prices starting at $350
⭐ Popular amenities Pool, Internet and Kitchen
🐾 Pet friendly homes 235 homes
🏊 Vacation rentals with pools 385 homes

Frequently Asked Questions

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

At the moment, there are 729 vacation homes from 2 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 235 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.

Top cities to visit

Top Vacation Destinations

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