Vacation rentals on Shelter Island - HomeToGo base64Hash Vacation rentals on Shelter Island - HomeToGo

Vacation rentals on Shelter Island

Find 1,038 available house rentals from 2 partners
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Top 15 Recommended vacation rentals on Shelter Island

Find your perfect vacation rental on Shelter Island from just $186 per night!

House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented house with yard, BBQ & terrace | Suitable for remote work | Pet-friendly

Shelter Island, Suffolk County, New York, United States
from $315
per night
Outstanding(1 rating)
from $315
per night
View deal
House Shelter Island
House ∙ 10 guests ∙ 5 bedrooms

Fully equipped ample vacation home with private pool, barbecue & yard

Shelter Island, Suffolk County, New York, United States
from $199
per night
from $199
per night
View deal
House Shelter Island
House ∙ 12 guests ∙ 6 bedrooms

Family-friendly vacation home with barbeque, yard & patio | Nature view

Shelter Island, Suffolk County, New York, United States
from $790
per night
Outstanding(21 ratings)
from $790
per night
View deal
House Shelter Island
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with private pool, barbeque & terrace | Perfect for remote work

Shelter Island, Suffolk County, New York, United States
from $771
per night
Outstanding(34 ratings)
from $771
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped vacation home with private pool, patio & barbeque

Shelter Island, Suffolk County, New York, United States
from $221
per night
Outstanding(37 ratings)
from $221
per night
View deal
House Shelter Island
House ∙ 12 guests ∙ 5 bedrooms

House with pool & garden

Shelter Island, Suffolk County, New York, United States
from $932
per night
Outstanding(20 ratings)
from $932
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

House with jacuzzi, yard & patio | Nature view | Good for workation

Shelter Island, Suffolk County, New York, United States
from $468
per night
Outstanding(49 ratings)
from $468
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 4 bedrooms

Fully equipped vacation home with yard, terrace & grill | Nature view

Shelter Island, Suffolk County, New York, United States
from $896
per night
Outstanding(36 ratings)
from $896
per night
View deal
House Shelter Island
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly wonderful house with patio, BBQ & hot tub | Nature view | Good for workation | Pet-friendly

Shelter Island, Suffolk County, New York, United States
from $848
per night
Outstanding(56 ratings)
from $848
per night
View deal
House Shelter Island
House ∙ 8 guests ∙ 3 bedrooms

House with private pool, garden & barbeque

Shelter Island, Suffolk County, New York, United States
from $487
per night
Outstanding(24 ratings)
from $487
per night
View deal
House Shelter Island
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly big house with patio, yard & barbeque | Suitable for remote work | Pets are welcome

Shelter Island, Suffolk County, New York, United States
from $757
per night
Excellent(49 ratings)
from $757
per night
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly spacious house with garden, terrace & private pool | Nature view | Perfect for remote work | Pets allowed

Shelter Island, Suffolk County, New York, United States
from $939
per night
Outstanding(39 ratings)
from $939
per night
View deal
House Shelter Island
House ∙ 7 guests ∙ 4 bedrooms

Family-oriented house with garden, grill & terrace | Nature view | Perfect for remote work | Pet-friendly

Shelter Island, Suffolk County, New York, United States
from $614
per night
Outstanding(22 ratings)
from $614
per night
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly spacious house with garden, barbecue & terrace | Nature view | Good for workation

Shelter Island, Suffolk County, New York, United States
from $543
per night
Outstanding(68 ratings)
from $543
per night
View deal
House Shelter Island
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with BBQ, patio & yard

Shelter Island, Suffolk County, New York, United States
from $1,012
per night
Outstanding(36 ratings)
from $1,012
per night
View deal

Vacation rentals and apartments with air conditioning

Cabin  Shelter Island
from $300
per night
Cabin ∙ 4 guests ∙ 3 bedrooms

Children-friendly beautiful cottage with terrace, grill & garden | Pets allowed

4.9
Outstanding(121 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
View deal
House  Shelter Island
from $677
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with private pool, barbeque & patio | Perfect for remote work

5.0
Outstanding(25 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
View deal
Cabin  Shelter Island
from $524
per night
Cabin ∙ 4 guests ∙ 3 bedrooms

Family-oriented cottage with terrace & BBQ | Nature view | Pets allowed

5.0
Outstanding(88 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House  Shelter Island
from $329
per night
House ∙ 6 guests ∙ 3 bedrooms

House with barbeque, yard & patio

5.0
Outstanding(39 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
View deal
House  Shelter Island
from $704
per night
House ∙ 8 guests ∙ 4 bedrooms

House with patio, BBQ & yard | Nature view

5.0
Outstanding(14 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
View deal
House  Shelter Island
from $321
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped house with yard & barbecue | Pets are welcome

5.0
Outstanding(12 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

House  Shelter Island
from $360
per night
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly charming house with grill, terrace & yard

4.9
Outstanding(40 ratings)
Shelter Island, Suffolk County, New York, United States
Fireplace
View deal
House  Shelter Island
from $454
per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly ample house with garden, barbecue & terrace | Nature view | Pets are welcome

4.6
Excellent(20 ratings)
Shelter Island, Suffolk County, New York, United States
Fireplace
View deal
House  Shelter Island
from $528
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly charming vacation home with yard, terrace & BBQ | Nature view | Pet-friendly

5.0
Outstanding(22 ratings)
Shelter Island, Suffolk County, New York, United States
Fireplace
View deal
See all offers

Best Vacation Home Deals on Shelter Island

Save up to 16%

Apartment Shelter Island
-16%
$343
from $289
per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Family-oriented charming rental apartment with garden | Perfect for remote work

5.0
Outstanding(32 ratings)
Shelter Island, Suffolk County, New York, United States
View deal

Search through the 1,038 vacation rentals featured on Shelter Island and find a wonderful spot for your getaway. All of the properties from our partner websites are instantly compared by the search engine , allowing you to save up to 15%.

Budget-friendly Vacation Rentals on Shelter Island

Find Fantastic yet Inexpensive Offers

Apartment Shelter Island
from $383
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with yard & patio

5.0
Outstanding(77 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
House Shelter Island
from $1,012
per night
House ∙ 6 guests ∙ 4 bedrooms

Fully equipped ample vacation home with patio, yard & hot tub | Nature view

5.0
Outstanding(27 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
House Shelter Island
from $234
per night
House ∙ 4 guests ∙ 2 bedrooms

Charming vacation home with 2 rooms for 4 persons

5.0
Outstanding(6 ratings)
Shelter Island, Suffolk County, New York, United States
View deal

Top-Rated Rentals and Accommodations on Shelter Island

Book Vacation Rental Offers with the Highest User Rating

House Shelter Island
from $1,103
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented house with hot tub, garden & terrace

5.0
Outstanding(200 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
House Shelter Island
from $711
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with grill, yard & terrace | Nature view

4.9
Outstanding(24 ratings)
Shelter Island, Suffolk County, New York, United States
View deal
House Shelter Island
from $1,626
per night
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented house with yard, barbeque & patio | Nature view | Close to the beach | Pets are welcome

5.0
Outstanding(21 ratings)
Shelter Island, Suffolk County, New York, United States
View deal

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Popular Rental Amenities on Shelter Island

  • Pool (456)
  • Pet-friendly (330)
  • WiFi (974)
  • Air conditioning (947)
  • Kitchen (766)
  • TV (863)
  • Washing machine (610)
  • Microwave (631)
  • Parking (46)
  • Grill (443)
  • Dishwasher (430)
  • Fireplace (480)

Nearly half of the accommodations include a pool, which makes Shelter Island a perfect place for vacationers looking to make a splash. In addition, more House rental have pools than any other type of accommodation. They are a great choice if you go in a group of 5, as that is the number of people they can welcome on average. Among these offers, 53 of them are situated within 2 miles of water.

Experience heaven on earth with Shelter Island vacation rentals

Shelter Island is merely 90 miles west of Manhattan, but offers a tranquil escape from the humdrum of city life. Reach the 8,000-acre island sandwiched between North and South Forks of Long Island by ferry, to explore the 17 miles of unspoiled coastline.

What are the best activities for families on Shelter Island?

Spend time outdoors with kids

With 12 miles of coastline and 2,000 acres of woodlands, marshes, and creeks, Mashomack Preserve covers the entire south-eastern part of Shelter Island.

A nearby vacation cabin ensures quick access to the Field House to explore the interactive exhibit about the Preserve’s ecosystem. Choose from five hiking trails of varying lengths and spot ospreys, piping plovers, and least terns.

Where are the unique attractions on Shelter Island?

Relax and unwind by the sea

Rent a beach house on the secluded and tranquil Shell Beach. This narrow beach extends into the Shelter Island Sound. Bask in the sun, watch plovers hop close to the waters edge, and be mesmerized by the colorful wildflowers in the vicinity, and the panoramic views of the South Fork and West Neck Harbor.

Information about vacation rentals on Shelter Island

🏡 Vacation rentals available 1,038 rentals
💳 Possible discounts up to 15%
🌙 Nightly prices starting at $186
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 330 homes
🏊 Vacation rentals with pools 457 homes
647 reviews
Shelter Island vacation rentals have an average rating of 4.9/5 on 647 reviews left by travelers.

Frequently Asked Questions

What is the typical price per night for a vacation home on Shelter Island?

The price of a night's stay on Shelter Island starts at $186. Average prices for house rentals are $1,159 per night. Apartment rentals on Shelter Island cost on average $525 per night.

How many vacation rentals are available for booking on Shelter Island?

There are currently 1,038 rentals on Shelter Island to browse and rent for your trip.

What amenities are most popular for vacation rentals on Shelter Island?

Travelers look for Pets allowed, Pool, and Internet when booking a vacation rental on Shelter Island.

How many vacation homes with pools are there on Shelter Island?

There are 457 vacation rentals across 2 providers on Shelter Island.

Are pets allowed in vacation homes on Shelter Island?

Absolutely, there are 330 vacation homes on Shelter Island that allow pets and the average nightly rate is $882.

What's the best month to travel to Shelter Island?

Shelter Island has its warmest time of year around July and August, with average nightly prices around $186.

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