Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Southampton NY

With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Shinnecock Hills Golf Course.

Exquisite New Hampton Home in a Perfect Location

East Hampton NY

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

FRESH FUN SPACIOUS! 4bed 4bath getaway RELAX and PLAY short walk 2 private beach

East Lyme CT

Located in Niantic, this vacation home is by the sea, within a 15-minute walk of Rocky Neck State Park and Rocky Neck State Beach.

Kitchen

Washer

Cozy 3-Bedroom Cape House Near Havens Beach

Sag Harbor NY

When you stay at this vacation home in Sag Harbor, you'll be on the beach, within a 5-minute walk of The Hamptons Beaches and Havens Beach.

Charming Waterfront Getaway — South Cove, Old Saybrook

Old Saybrook CT

Located in Old Saybrook, this vacation home is within a 5-minute drive of General William Hart House and Katharine Hepburn Cultural Arts Center.

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.

Pool

Kitchen

Beach House

East Lyme CT

Located in Niantic, this vacation home is by the sea, a 3-minute drive from Attawan Beach and 6 minutes from McCook Point Beach.

Private 2.1 acre gated home with heated pool and tennis & pickleball court

Southampton NY

With a stay at this vacation home in Southampton, you'll be near the beach, within a 10-minute drive of The Hamptons Beaches and Elizabeth A. Morton National Wildlife Refuge.

Beautiful Private 4 BR, Heated Pool. Close to Everything!

East Hampton NY

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

Cozy 5 Bedroom With Wi-fi And Air Condition

Wainscott NY

$1,707 nightly

$1,950 total

Jun 16 - Jun 17

Total with taxes and fees

With a stay at this vacation home in Wainscott, you'll be within a 10-minute drive of The Hamptons Beaches and SagPond Vineyards.

Air conditioning

The Cooper-Burke House

Sag Harbor NY

A stay at this vacation home places you in the heart of Sag Harbor, within a 15-minute walk of The Hamptons Beaches and Sag Harbor Marine Park.

Hamptons Cousy, Spacious, Family Home by the beach

Hampton Bays NY

With a stay at this vacation home in Hampton Bays, you'll be a 1-minute drive from The Hamptons Beaches and 10 minutes from Shinnecock Hills Golf Course.

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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.