Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Large Charming Historic House close to Beaches

Clinton CT

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.

Kitchen

Washer

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Jamesport NY

Located in Riverhead, this vacation home is within a 15-minute walk of Terra Vite North Fork Winery & Vineyard and Jason's Vineyard.

Kitchen

Washer

Walk to the beach at Black Point, Niantic, Ct.

Niantic CT

When you stay at this vacation home in Niantic, you'll be near the beach and within a 5-minute drive of Attawan 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

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Amagansett NY

With a stay at this vacation home in Amagansett (Beach Hampton), you'll be within a 10-minute walk of The Hamptons Beaches and Amagansett Beach.

Washer

Dryer

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor NY

Located in Sagaponack, this vacation home is by the sea, a 4-minute drive from Wolffer Estates Vineyard and 5 minutes from South Fork Natural History Museum and Nature Center.

Pool

Hot Tub

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Montauk NY

With a stay at this vacation home in Montauk, you'll be on the beach, just a 1-minute walk from The Hamptons Beaches and 10 minutes by foot from Second House Museum.

Pool

Kitchen

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Hampton Bays NY

$1,085 nightly

$1,240 total

Dec 14 - Dec 15

Total with taxes and fees

Located in Hampton Bays, this vacation home is on the waterfront, within a 5-minute drive of The Hamptons Beaches and Ponquogue Beach.

Hot Tub

Kitchen

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Old Lyme CT

Located in Old Lyme, this vacation home is by the ocean, within a 10-minute drive of Lyme Academy of Fine Arts and Rocky Neck State Park.

Kitchen

Washer

Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

East Hampton NY

When you stay at this vacation home in East Hampton, you'll be near the beach, within a 5-minute drive of The Jewish Center of the Hamptons and Home Sweet Home Museum.

Kitchen

Washer

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

East Hampton NY

A stay at this vacation home places you in the heart of East Hampton, within a 5-minute drive of The Hamptons Beaches and Three Mile Harbor.

Pool

Kitchen

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

Hampton Bays NY

Located in Hampton Bays, this vacation home is by the sea, within a 5-minute drive of Meschutt Beach and The Hamptons Beaches.

Hot Tub

Kitchen

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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.