Shelter Island Vacation Rentals

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.

With a stay at this vacation home in Clinton, you'll be near the beach, just a 4-minute walk from Adam Stanton House and General Store Museum and 12 minutes by foot from Clinton Town Beach.

With a stay at this vacation home in East Hampton (East Hampton North), you'll be within a 5-minute drive of The Hamptons Beaches and Amelia Cottage Museum.

With a stay at this vacation home in Riverhead, you'll be just steps from Clovis Point and Clovis Point Vineyard & Tasting Room.

Located in Clinton, this vacation home is by the ocean, within a 5-minute drive of Clinton Plaza Shopping Center and Adam Stanton House and General Store Museum.

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.

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.

Located in Clinton, this vacation home is within a 5-minute drive of Hammonasset Beach State Park and Chamard Vineyards.

With a stay at this vacation home in Jamesport, you'll be a 1-minute walk from Jason's Vineyard and 7 minutes by foot from Clovis Point.

Located in Riverhead, this vacation home is a 2-minute drive from Roanoke Vineyards and 6 minutes from Long Island National Golf Club.

Located in Sagaponack, this vacation home is in a rural location, a 4-minute drive from Wolffer Estates Vineyard and 6 minutes from South Fork Natural History Museum and Nature Center.

With a stay at this vacation home in Greenport (Pipes Cove), you'll be within a 10-minute walk of Railroad Museum of Long Island and East End Seaport Maritime Museum.