Shelter Island Resorts

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Resorts in Shelter Island

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway, Montauk, NY

$511

per night

May 30 - May 31

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.

Pool

On private beach

Water's Edge Resort & Spa

1525 Boston Post Road, Westbrook, CT

$265

per night

May 27 - May 28

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.

Pool

On private beach

Brand New Waterfront - Chic & Sophisticated Unit # 703

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 10-minute walk of The Hamptons Beaches and Lake Montauk.

Air conditioning

Gym

Brand New Waterfront - Chic & Sophisticated

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 10-minute walk of The Hamptons Beaches and Lake Montauk.

Air conditioning

Gym

Brand New Waterfront - Chic & Sophisticated Unit # 702

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 10-minute walk of The Hamptons Beaches and Lake Montauk.

Air conditioning

Gym

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

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

Available July 21-28, 2023

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

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

Brand New Waterfront - Chic & Sophisticated

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 10-minute walk of The Hamptons Beaches and Lake Montauk.

Air conditioning

Gym

Brand New Waterfront - Chic & Sophisticated Unit # 704

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 10-minute walk of The Hamptons Beaches and Lake Montauk.

Air conditioning

Gym

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

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

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

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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.