Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays NY

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

Hot Tub

Kitchen

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Riverhead NY

With a stay at this vacation home in Riverhead, you'll be within a 15-minute drive of Splish Splash Water Park and Roanoke Vineyards.

Hot Tub

Kitchen

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.

Pool

Kitchen

The SandPiper

Greenport, NY

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.

Kitchen

Washer

Large Charming Historic House close to Beaches

Clinton CT

With a stay at this vacation home in Clinton, you'll be near the beach, within a 5-minute drive of Hammonasset Beach State Park and Adam Stanton House and General Store Museum.

Kitchen

Washer

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton NY

Located in Southampton, this vacation home is within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.

Pool

Hot Tub

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Southampton NY

When you stay at this vacation home in Southampton, you'll be by the sea, a 4-minute drive from The Hamptons Beaches and 6 minutes from Cooper's Beach.

Kitchen

Washer

Aqua Vista

Greenport, NY

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.

Kitchen

Washer

2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

East Lyme CT

Located in Niantic, this vacation home is on the waterfront, within a 10-minute drive of Tumbleweeds and Amtrak Beach.

Kitchen

Washer

Luxurious midcentury modern glass house in the woods, chefs kitchen & great art

Old Lyme CT

Located in Old Lyme, this vacation home is on a lake, within a 5-minute drive of Goose Island and Lawrence & Memorial Family Medicine.

Kitchen

Washer

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.

Washer

Dryer

1820 Whaling Captain's Home - A walk to a coffee or cocktail!

Greenport NY

A stay at this vacation home places you in the heart of Greenport, within a 10-minute walk of Greenport Harbor Brewing Company and Eastern Long Island Hospital.

Kitchen

Washer

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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.