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2026-06-30
2026-07-01
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Private Villas in Deep Hole

Barefoot Breeze

5392 North Hibiscus Dr, Deep Hole, United States Show map

Barefoot Breeze Villa Deep Hole entices guests to enjoy cycling and offers proximity to the Captain Timothy Hill House, located just 8 minutes' stroll away. Featuring a patio, the Deep Hole holiday… More

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Channel Watch - Waterfront Home With Private Pier!

6397 Pine Drive, Deep Hole, United States Show map

Staying at the 2-bedroom Channel Watch - Waterfront Home With Private Pier! Deep Hole, guests can easily reach the Maui Jack's Waterpark, located just 1.6 km away. More

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Shady Grove - Water Views, Fireplace!

5454 Amrien Circle Drive, Deep Hole, United States Show map

Located within 3 km of Chincoteague National Wildlife Refuge, the 2-bedroom Shady Grove - Water Views, Fireplace! Deep Hole villa provides access to various tourist attractions in the vicinity. More

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Hailey'S Roundhouse - New & Unique Home W/ Water Access!

5411 Cedar Drive, Deep Hole, United States Show map

Situated 3.3 km from Little Oyster Bay, the 2-bedroom Hailey'S Roundhouse - New & Unique Home W/ Water Access! Deep Hole entices guests to explore various tourist attractions in the area. More

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Tranquility - Brand New Home In Quiet Location!

5423 Deep Hole Road, Deep Hole, United States Show map

Staying at the 2-bedroom Tranquility - Brand New Home In Quiet Location! Deep Hole, guests can easily reach the Chincoteague Pony Centre, located a mere 1.8 km away. More

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Island Sage

5303 Meadow Drive, Deep Hole, United States Show map

Situated around 25 minutes' walk from the Chincoteague Island Library, Island Sage Villa Deep Hole entices guests to explore various tourist attractions in the area. Guests can enjoy cycling at the… More

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Beach Bungalow - Pet Friendly Cottage W/ Amazing Views!

6309 Highland Park Drive, Deep Hole, United States Show map

Beach Bungalow - Pet Friendly Cottage W/ Amazing Views! Deep Hole offers proximity to nearby tourist spots, such as Deep Hole Creek, situated a 20-minute walk away. More

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Tall Pines - Pet Friendly With Screened Porch!

5328 Oak Drive, Deep Hole, United States Show map

Offering a location approximately a 25-minute walk from Captain Timothy Hill House, the 1-bedroom Tall Pines - Pet Friendly With Screened Porch! Deep Hole villa gives access to various tourist spots… More

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Oyster Bay Oasis

5609 Hibiscus Drive, Deep Hole, United States Show map

Oyster Bay Oasis Villa Deep Hole is located 9 minutes' walk from Little Oyster Bay and offers guests to enjoy cycling. More

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Sunset Bay Cottage - Main Street Charm With Water Views!

4496 Main Street, Deep Hole, United States Show map

During the stay at Sunset Bay Cottage - Main Street Charm With Water Views! Deep Hole, guests can indulge in mini golf or visit the Captain Timothy Hill House, located a 14-minute walk away. More

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'Chincoteague Charm' Escape W/ Bikes & Yard Games!

Deep Hole, United States Show map

Situated just 5 minutes' walk from the Chincoteague Island Waterman's Memorial, the family 'Chincoteague Charm' Escape W/ Bikes & Yard Games! Deep Hole villa provides access to numerous tourist… More

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Sunrise Shore - Waterfront With Private Pool & Hot Tub!

5314 Sunrise Shore Drive, Deep Hole, United States Show map

Staying at the 3-bedroom Sunrise Shore - Waterfront With Private Pool & Hot Tub! Deep Hole villa, guests can easily reach the historic red-&-white Assateague Lighthouse, located about a 10-minute… More

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