Shelter Island Heights Vacation Rentals

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Vacation Rentals in Shelter Island Heights

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.

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Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

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.

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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.

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Hot Tub

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 Cooper's Beach.

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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.

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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.

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Dryer

Historic House Getaway

Peconic NY

With a stay at this vacation home in Peconic, you'll be within a 5-minute drive of Sannino's Bella Vita Vineyard and Goldsmith's Inlet Park.

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.

Direct Waterfront Beach House with Panoramic Views

East Lyme CT

When you stay at this vacation home in Niantic, you'll be on the beach, within a 10-minute walk of Attawan Beach and McCook Point Beach.

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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.

Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week

east quogue NY

With a stay at this vacation home in East Quogue, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and Quogue Community Hall.

Hamptons Modern Retreat NEW CONS

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.

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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.