Shelter Island Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Shelter Island hotels

Vacation Rentals in Shelter Island

The Hampton Sack a cheerful relaxing beach cottage

East Hampton NY

With a stay at this vacation home in East Hampton, you'll be within a 10-minute walk of The Hamptons Beaches and Three Mile Harbor.

Kitchen

Dryer

Cozy sun drenched beach cottage private beach & hot tub. Year round beach escape

Montauk NY

With a stay at this vacation home, you'll be centrally located in Montauk, a 1-minute drive from The Hamptons Beaches and 12 minutes from Montauk Point Lighthouse.

Hot Tub

Kitchen

Phenomenal One Bedroom Cottage in Historic Old Lyme, Connecticut

Old Lyme CT

With a stay at this vacation home in Old Lyme, you'll be within a 15-minute walk of Old Lyme Historical Society and Connecticut River.

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Southold NY

Located in Southold, this vacation home is on the waterfront, a 4-minute drive from Croteaux Vineyards and 7 minutes from Raphael Winery.

Peaceful and Private 4-Bedroom Home in Southampton

Southampton NY

With a stay at this vacation home in Southampton, you'll be within a 15-minute drive of The Hamptons Beaches and Southampton Golf Range.

Hot Tub

Kitchen

Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

Old Saybrook CT

Located in Old Saybrook (Saybrook Manor), this vacation home is within a 5-minute drive of Saybrook Country Barn and Harvey's Beach.

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

Westbrook CT

With a stay at this vacation home in Westbrook (Westbrook Center), you'll be within a 15-minute drive of Hammonasset Beach State Park and Tanger Outlets.

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Montauk NY

When you stay at this vacation home in Montauk, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Hampton Bays NY

When you stay at this vacation home in Hampton Bays, you'll be on the waterfront, within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.

Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

Niantic CT

Located in Niantic, this vacation home is by the sea, within a 5-minute walk of Rocky Neck State Park and Rocky Neck State Beach.

Aqua Vista

Greenport, NY

$337 nightly

$385 total

Sep 8 - Sep 9

Total with taxes and fees

With a stay at this vacation home in Greenport (Pipes Cove), you'll be steps from Railroad Museum of Long Island and 3 minutes by foot from East End Seaport Maritime Museum.

Charming Mattituck Retreat Near the Bay with Modern Updates

Mattituck NY

Located in Mattituck, this vacation home is a 4-minute drive from Love Lane and 6 minutes from Cutchogue Village Green.

Don't see what you're looking for?

See all available properties in Shelter Island

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.