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 most Recommended Vacation Rentals on Shelter Island
Discover your ideal Shelter Island vacation rental with real-time comparisons of 658 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.
Vacation Houses With Pools
Dog-Friendly Vacation Rentals
Vacation rentals with a balcony
Budget-friendly rental options
Enjoy affordable vacation rentals on Shelter Island offering exceptional value for money
Top-Rated Vacation rentals on Shelter Island
Book the highest-rated Shelter Island vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money
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 Features & Amenities on Shelter Island
More than 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 3, as that is the number of people they can welcome on average. Among these offers, 57 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 | 658 rentals |
|---|---|
| 🌙 Nightly prices starting at | $121 |
| ⭐ Popular amenities | Pool, Pets allowed and Internet |
| 🐾 Pet friendly homes | 200 homes |
| 🏊 Vacation rentals with pools | 332 homes |
Frequently Asked Questions
What is the average nightly price for a vacation home on Shelter Island?
The price of a night's stay on Shelter Island starts at $121. $1,174 is the average nightly price for house rentals on Shelter Island. Cottages on Shelter Island cost $631 per night on average.
How many vacation homes are available for booking on Shelter Island?
There are currently 658 vacation homes on Shelter Island to choose from and book for your upcoming trip.
What amenities are most popular for vacation homes on Shelter Island?
Three most popular amenities for vacation home rentals on Shelter Island include accommodations with: Pets allowed, Pool, and Internet.
How many vacation rentals with pools are there on Shelter Island?
There are 332 vacation homes across 3 providers on Shelter Island.
Are dogs allowed in vacation homes on Shelter Island?
Absolutely, there are 200 vacation rentals on Shelter Island that allow dogs , with an average nightly price of $835.
Top cities to visit
- New York
- Carmel
- Montauk
- Newport
- Springfield
- Fire Island
- Providence
- Narragansett
- Sag Harbor
- Englewood
- Hoboken
- New Haven
- Norwalk
- White Plains
- East Hampton
- Times Square
- Westerly
- Fall River
- Mount Vernon
- Danbury
- Stamford
- Portsmouth
- Greenwich
- Bridgeport
- Old Saybrook
- Yonkers
- Waterbury
- Amherst
- Milford
- Beacon
- Hartford, CT
- New London
- Stonington
- Southampton
- Jamestown
- Northampton
- Fairhaven
- Port Jefferson
- Little Compton
- Misquamicut
- Charlestown
- Chilmark
- Westhampton
- Middletown
- Old Lyme
- Westbrook
- Quogue
- South Kingstown
- Weehawken
- Lakeville
Most Popular Destinations
- Vacation rentals in the Outer Banks (OBX)
- Cabin rentals in Gatlinburg, TN
- Cabin rentals in Hocking Hills, OH
- Cabin rentals in Broken Bow, OK
- Vacation rentals in Myrtle Beach
- Vacation rentals & cabins in Pigeon Forge
- Vacation rentals in Gulf Shores
- Vacation rentals in Scottsdale
- Vacation rentals in Tybee Island
- Vacation rentals in Vancouver
- Vacation rentals in Destin
- Vacation rentals in North Myrtle Beach
- Vacation rentals in Panama City Beach
- Vacation rentals in Yellowstone
- Vacation rentals in Emerald Isle
- Vacation rentals in Door County
- Vacation rentals & cabins near Lake Tahoe
- Vacation rentals & cabins in Branson
- Vacation rentals in Key West
- Vacation rentals in Cape Cod
- Vacation rentals in Rosemary Beach
- Cabin rentals in the Smoky Mountains, NC
- Vacation rentals & cabins in Yosemite
- Vacation rentals in Orlando
- Vacation rentals in Hilton Head Island
- Vacation rentals in Cape Coral
- Vacation rentals in Oak Island
- Vacation rentals in Anna Maria Island
- Vacation rentals & cabins in the Great Smoky Mountains
- Vacation rentals in San Diego
- Vacation rentals in Miami
- Vacation rentals in Siesta Key
- Vacation rentals in Nashville
- Vacation rentals & cabins in Big Bear Lake
- Vacation rentals & cabins in Logan
- Vacation rentals & cabins in Estes Park
- Vacation rentals in Nashville
- Vacation rentals in Orange Beach
- Vacation rentals in Las Vegas
- Vacation rentals & cabins in Glacier National Park
- Vacation rentals in Charleston
- Vacation rentals in Ocean City
- Vacation rentals in New Orleans
- Vacation rentals in Kauai
- Vacation rentals & cabins in Sedona
- Vacation rentals in Maui
- Vacation rentals in Florida
- Vacation rentals & cabins in Colorado
- Vacation rentals & cabins in Zion National Park
- Vacation rentals on Mackinac Island
- Vacation rentals in South Padre Island
- Vacation rentals in Chicago
- Vacation rentals in Virginia Beach
- Vacation rentals in Palm Springs
- Vacation rentals in Lake Ozark
- Vacation rentals in Atlanta
- Vacation rentals & cabins in Tennessee
- Vacation rentals in Breckenridge
- Vacation rentals in New York