Shelter Island Resorts

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Resorts in Shelter Island

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$466 nightly

$532 total

Dec 15 - Dec 16

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

$244 nightly

$281 total

Dec 14 - Dec 15

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

Brand New Waterfront - Chic & Sophisticated Unit # 702

Montauk NY

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 5-minute walk of Lake Montauk and Montauk Marine Basin.

Brand New Waterfront - Chic & Sophisticated

Montauk NY

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 5-minute walk of Lake Montauk and Montauk Marine Basin.

Air conditioning

Gym

Duryea's Sunset Cottages

80 Firestone Road Montauk NY

With a stay at Duryea's Sunset Cottages in Montauk, you'll be on the beach, just a 5-minute walk from The Hamptons Beaches and 12 minutes by foot from Shadmoor State Park.

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 5-minute walk of Lake Montauk and Montauk Marine Basin.

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 5-minute drive of Westbrook Town Beach and Tanger Outlets.

Pool

Hot Tub

Water's Edge Resort & Spa May 23, 2025 - May 30, 2025

Westbrook CT

With a stay at this resort in Westbrook (Westbrook Center), you'll be within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.

Pool

Hot Tub

Brand New Waterfront - Chic & Sophisticated Unit # 704

Montauk NY

With a stay at this resort in Montauk (Culloden Shores), you'll be within a 5-minute walk of Lake Montauk and Montauk Marine Basin.

Air conditioning

Gym

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

Westbrook CT

Located in Westbrook (Westbrook Center), this resort is within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.

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 Napeague State Park and The Hamptons Beaches.

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

Westbrook CT

Located in Westbrook (Westbrook Center), this resort is within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.

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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.