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 746 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, 58 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 | 746 rentals |
|---|---|
| 🌙 Nightly prices starting at | $135 |
| ⭐ Popular amenities | Pool, Pets allowed and Internet |
| 🐾 Pet friendly homes | 233 homes |
| 🏊 Vacation rentals with pools | 395 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 $135. $1,507 is the average nightly price for house rentals on Shelter Island. Cottages on Shelter Island cost $729 per night on average.
How many vacation homes are available for booking on Shelter Island?
There are currently 746 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 395 vacation homes across 2 providers on Shelter Island.
Are dogs allowed in vacation homes on Shelter Island?
Absolutely, there are 233 vacation rentals on Shelter Island that allow dogs , with an average nightly price of $972.
Top cities to visit
- New York
- Carmel
- Montauk
- Newport
- Springfield
- Fire Island
- Narragansett
- Providence
- Englewood
- Norwalk
- Hoboken
- New Haven
- East Hampton
- White Plains
- Sag Harbor
- Fall River
- Westerly
- Portsmouth
- Mount Vernon
- Times Square
- Danbury
- Stamford
- Greenwich
- Old Saybrook
- Waterbury
- Bridgeport
- Yonkers
- Amherst
- Milford
- Jamestown
- Southampton
- Hartford, CT
- Stonington
- Beacon
- New London
- Amagansett
- Northampton
- Little Compton
- Misquamicut
- Port Jefferson
- Fairhaven
- Charlestown
- Chilmark
- Westhampton
- Southold
- Old Lyme
- Middletown
- Branford
- Westbrook
- South Kingstown
Most Popular Destinations
- Vacation rentals in the Outer Banks (OBX)
- Vacation rentals in Gatlinburg, TN
- Cabin rentals in Hocking Hills, OH
- Vacation rentals in Broken Bow, OK
- Vacation rentals in Myrtle Beach
- Vacation rentals in Pigeon Forge
- Vacation rentals in Gulf Shores
- Vacation rentals in Vancouver
- Vacation rentals in Tybee Island
- Vacation rentals in Scottsdale
- Vacation rentals in North Myrtle Beach
- Vacation rentals in Destin
- Vacation rentals in Emerald Isle
- Vacation rentals in Door County
- Vacation rentals in Panama City Beach
- Vacation rentals near Lake Tahoe
- Vacation rentals in Cape Cod
- Vacation rentals in Rosemary Beach
- Vacation rentals in Key West
- Cabin rentals in the Smoky Mountains, NC
- Vacation rentals in Branson
- Vacation rentals in Yellowstone
- Vacation rentals in Anna Maria Island
- Vacation rentals in Oak Island
- Vacation rentals in Yosemite
- Vacation rentals & cabins in Logan
- Vacation rentals in Cape Coral
- Vacation rentals in Orlando
- Vacation rentals in Hilton Head Island
- Vacation rentals in Big Bear Lake
- Vacation rentals in Siesta Key
- Vacation rentals in Nashville
- Vacation rentals in the Great Smoky Mountains
- Vacation rentals in Ocean City
- Vacation rentals in Charleston
- Vacation rentals in Miami
- Vacation rentals in Orange Beach
- Vacation rentals in San Diego
- Vacation rentals in Kauai
- Vacation rentals in Estes Park
- Vacation rentals in Florida
- Vacation rentals in Nashville
- Vacation rentals in South Padre Island
- Vacation rentals in Sedona
- Vacation rentals on Mackinac Island
- Vacation rentals in Glacier National Park
- Vacation rentals in Las Vegas
- Vacation rentals in New Orleans
- Vacation rentals in Colorado
- Vacation rentals in New York
- Vacation rentals in the Isle of Palms
- Vacation rentals in Tennessee
- Vacation rentals in Blue Ridge
- Vacation rentals in Ruidoso
- Vacation rentals in Maui
- Vacation rentals in Virginia Beach
- Vacation rentals in Palm Springs
- Vacation rentals in North Carolina
- Vacation rentals in Lake Ozark