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.
Top 15 Recommended vacation rentals on Shelter Island
Find your perfect vacation rental on Shelter Island from just $186 per night!
Vacation rentals and apartments with air conditioning
Vacation rentals with a balcony
Vacation Rentals With Fireplaces
Best Vacation Home Deals on Shelter Island
Save up to 16%
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
Top-Rated Rentals and Accommodations on Shelter Island
Book Vacation Rental Offers with the Highest User Rating
Why choose HomeToGo?
Securely pay and stay your way
Choose local, trusted payment methods, plus trip insurance and add-on services.
Award-winning customer service
Experience seamless, hands-on support for any booking questions or concerns.
Verified reviews
Trust in the quality and comfort of your stay with verified guest reviews.
Price clarity, no surprises
Spend your budget exactly as planned by comparing thousands of providers.
Smart search made simple
Transform vacation planning into a joy with advanced, AI-powered search tools.
Find your dream stay
Explore 15 million+ rentals, the world’s biggest selection of vacation homes.
Popular Rental Amenities on Shelter Island
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.
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.
Most Popular Destinations
- Cabin rentals in Gatlinburg, TN
- Vacation rentals in Yellowstone
- Vacation rentals in the Outer Banks
- Cabin rentals in Hocking Hills, OH
- Vacation rentals & cabins in Pigeon Forge
- Vacation rentals in Myrtle Beach
- Vacation Rentals in Vancouver, WA
- Vacation rentals in Vancouver
- Vacation rentals & cabins near Lake Tahoe
- Cabin rentals in Broken Bow, OK
- Vacation rentals & cabins in Yosemite
- Vacation rentals in Orlando
- Vacation rentals & cabins in Glacier National Park
- Vacation rentals in Gulf Shores
- Vacation rentals in San Diego
- Vacation rentals in Las Vegas
- Vacation rentals in Destin
- Vacation rentals & cabins in Branson
- Vacation rentals in Nashville
- Vacation rentals & cabins in Estes Park
- Vacation rentals in Key West
- Vacation rentals in Virginia Beach
- Vacation rentals in New Orleans
- Vacation rentals in Miami
- Cabin rentals in the Smoky Mountains, NC
- Vacation rentals in Panama City Beach
- Vacation rentals & cabins in Zion National Park
- Vacation rentals in Tybee Island
- Vacation rentals in Door County
- Vacation rentals & cabins in the Great Smoky Mountains
- Vacation rentals in Chicago
- Vacation rentals & cabins in Big Bear Lake
- Vacation rentals & cabins in Sedona
- Vacation rentals on Block Island
- Vacation rentals in Maui
- Vacation rentals in Kauai
- Vacation rentals in Colorado Springs
- Vacation rentals in Nashville
- Vacation rentals & cabins in Colorado
- Vacation rentals in Siesta Key
- Vacation rentals in Charleston
- Vacation rentals in Palm Springs
- Vacation rentals in Orange Beach
- Vacation rentals in Anna Maria Island
- Vacation rentals in Paris
- Vacation rentals in Florida
- Vacation rentals in Cape May
- Vacation rentals in Atlanta
- Vacation rentals in Breckenridge
Top cities to visit
- New York
- Carmel
- Newport
- Montauk
- Springfield
- Narragansett
- Fire Island
- Providence
- Sag Harbor
- New Haven
- Norwalk
- Hoboken
- Westerly
- White Plains
- Englewood
- Stamford
- Times Square
- Fall River
- Mount Vernon
- Danbury
- East Hampton
- Old Saybrook
- Greenwich
- Bridgeport
- Yonkers
- Waterbury
- Amherst
- Portsmouth
- Hartford, CT
- Beacon
- Milford
- New London
- Stonington
- Southampton
- Northampton
- Port Jefferson
- Jamestown
- Little Compton
- Misquamicut
- Fairhaven
- Westhampton
- Old Lyme
- Middletown
- Westbrook
- Charlestown
- Lakeville
- Quogue
- Chilmark
- Weehawken
- Tiverton