Shelter Island Resorts

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Resorts in Shelter Island

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$1,110 nightly

$1,268 total

Jun 21 - Jun 22

Total with taxes and fees

Located in Montauk, Gurney's Montauk Resort & Seawater Spa is by the ocean, a 3-minute drive from Hither Hills State Park and 7 minutes from Shadmoor State Park.

On private beach

Pool

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

$364 nightly

$419 total

Jun 30 - Jul 1

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing Premium Outlets.

On private beach

Pool

Ocean Colony Beach and Tennis Club

2004 Montauk Hwy Amagansett NY

With a stay at Ocean Colony Beach and Tennis Club in Amagansett (Napeague), you'll be steps from The Hamptons Beaches and Napeague State Park.

Pool

Pet friendly

Brand New Waterfront - Chic & Sophisticated

Montauk NY

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

Air conditioning

Gym

Duryea's Sunset Cottages

80 Firestone Road Montauk NY

When you stay at Duryea's Sunset Cottages in Montauk, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

On private beach

Hot Tub

Brand New Waterfront - Chic & Sophisticated Unit # 703

Montauk NY

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

Air conditioning

Gym

Brand New Waterfront - Chic & Sophisticated Unit # 702

Montauk NY

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

Air conditioning

Gym

Brand New Waterfront - Chic & Sophisticated Unit # 704

Montauk NY

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

Air conditioning

Gym

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Westbrook CT

With a stay at this resort in Westbrook (Westbrook Center), you'll be within a 15-minute drive of Hammonasset Beach State Park and Westbrook Town Beach.

Pool

Hot Tub

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Westbrook CT

With a stay at this resort in Westbrook (Westbrook Center), you'll be within a 15-minute drive of Hammonasset Beach State Park and Westbrook Town Beach.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Shelter Island

View all properties

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.