Luxury accommodations in Deep Hole

The 2-bedroom Serenity At Deep Hole Hideaway - Pet Friendly! villa is nestled only a 9-minute walk from Little Oyster Bay and can accommodate up to 6 guests. Located in the vicinity of Oyster Bay… More

The 4-bedroom Barefoot Breeze Villa Deep Hole entices guests to enjoy cycling and offers proximity to Captain Timothy Hill House, located just 8 minutes' stroll away. The Deep Hole holiday home is… More

Situated approximately a 25-minute walk from Chincoteague Island Library, the 36 m² Assateague Inn 103-S Deep Hole can host up to 4 guests in Deep Hole. Set right around the corner from The Brant… More

Staying at the 3-bedroom Channel Watch - Waterfront Home With Private Pier! Deep Hole, guests can visit the historic red-&-white Assateague Lighthouse, which is nearly a 25-minute walk away. Offering… More

Featuring an outdoor swimming pool, the 36 m² Assateague Inn 105-S Deep Hole is about 5 minutes' walk from The Brant Gift Shop. Offering an aqua park and a golf course, this 1-bedroom apartment is… More

Situated nearly a 25-minute walk from Veteran's Memorial Park, the 36 m² Assateague Inn 203-S Deep Hole can host up to 4 guests in Deep Hole. Set right near The Brant Gift Shop, this 1-bedroom… More

The family-friendly 'Chincoteague Charm' Escape W/ Bikes & Yard Games! Villa Deep Hole hosts up to 12 guests a mere 8 minutes' walk from Captain Timothy Hill House and offers rental hire. More

The 3-bedroom Hailey'S Roundhouse - New & Unique Home W/ Water Access! Deep Hole is nestled just a 9-minute walk from Museum of Chincoteague and can accommodate up to 9 guests. Located about 3 km… More

Offering a location 2.8 km from Chincoteague Island Library, the 3-bedroom Admiral Benbow - Contemporary Home With Shared Boat Ramp Deep Hole gives access to various tourist spots in the area. More

The 4-bedroom Tranquility - Brand New Home In Quiet Location! Deep Hole hosts up to 11 guests and provides proximity to Little Oyster Bay, situated merely 0.7 km away. Providing guests with Wi-Fi and… More

Offering a location 25 minutes on foot from Little Oyster Bay, Blue Pointe Bayside - Cozy, Waterfront Home! Deep Hole gives access to various tourist spots in the area. Offering island tours, this 3… More

The 2-bedroom Cockleshell Cottage - Pet Friendly & Handicap Accessible! Deep Hole hosts up to 10 guests and provides proximity to Captain Timothy Hill House, situated a mere 0.6 km away. Providing… More

Situated around 25 minutes' walk from Chincoteague National Wildlife Refuge, the 3-bedroom Island Sage Villa Deep Hole offers guests to enjoy an aqua park and a golf course. This property features… More

Bellas Beach Retreat - Assateague Inn 211 Deep Hole is located 1.1 km from Museum of Chincoteague and a 9-minute walk from Maui Jack's Waterpark. Offering access to an outdoor swimming pool, this… More

Offering a location 4.2 km from Assateague Beach, the 2-bedroom Tall Pines - Pet Friendly With Screened Porch! Deep Hole villa gives access to various tourist spots in the area. With a maximum… More

Nestled 4.7 km from the historic red-&-white Assateague Lighthouse, the 2-bedroom Beachgrass Bungalow Deep Hole is boasting an aqua park and a golf course for guests' enjoyment. Located approximately… More

Up to 8 guests can stay at the 4-bedroom Belle Of The Bay - Beautiful Custom Waterfront Home! Deep Hole and enjoy Oyster Bay, located approximately a 5-minute walk away. Providing guests with Wi-Fi… More

The 3-bedroom Blue Sea Star - Beautiful Pet Friendly Home! Deep Hole is nestled about a 5-minute walk from Captain Timothy Hill House and can accommodate up to 12 guests. Located 4.2 km from… More

During the stay at Sunset Bay Cottage - Main Street Charm With Water Views! Deep Hole, guests can indulge in mini golf or visit Captain Timothy Hill House, located a 14-minute walk away. The 3… More

The 3-bedroom Sunrise Shore - Waterfront With Private Pool & Hot Tub! Deep Hole villa hosts up to 14 guests and is nestled within 25 minutes' walk of natural sites such as Maui Jack's Waterpark. More

Featuring island tours to make your visit more entertaining, Cedar Cove - Waterfront Home With Fire Pit! Deep Hole is a 10-minute drive from Chincoteague Veteran's Memorial Park. The 3-bedroom villa… More