Vacation Rentals in Deep Hole

Nestled nearly a 20-minute walk from the Chincoteague National Wildlife Refuge, the 3-bedroom Conch Shell - Waterfront Villa With Wrap Around Deck! Deep Hole entices guests to explore various tourist… More

The 3-bedroom Admiral Benbow - Contemporary Home With Shared Boat Ramp Deep Hole is located 2.8 km from the Chincoteague Island Library and invites guests to join boating and fishing. More

Catch Of The Day Villa Deep Hole is located merely 1.9 km from the Chincoteague Pony Centre and allows guests to enjoy cycling. More

The Happy Crab Villa Deep Hole is located around a 25-minute walk from the Captain Timothy Hill House and provides cycling for active guests. Located in proximity to the Museum of Chincoteague, the… More

Situated about a 5-minute walk from the Museum of Chincoteague, Stoney Point Villa Deep Hole entices guests with cycling in the area. Located 1.8 km from the Chincoteague National Wildlife Refuge… More

Staying at Assateague Inn 104-S Deep Hole, guests can visit the Brant, located around 5 minutes' walk away. Offering access to a private swimming pool, this apartment is just 300 m from the… More

Located 25 minutes' walk from the Museum of Chincoteague, Serenity At Oyster Bay, Water Access & Firepit! Deep Hole villa gives access to various tourist sites in the vicinity. The 3-bedroom holiday… More

Located a mere 0.6 km from the Captain Timothy Hill House, Deja Blue Villa Deep Hole offers opportunities for cycling in the area. This Deep Hole villa boasts an indoor water park and a private… More

Up to 9 guests can stay at Endless Summer - Pet Friendly With Screened Porch! Deep Hole villa and enjoy the Piney Island, located a 6-minute walk away. More

Along with proximity to the Chincoteague Pony Centre, just 5 minutes' walk away, The Blue Crab Villa Deep Hole offers opportunities for cycling in the area. More

Located only a 14-minute walk from the Museum of Chincoteague, the 3-bedroom Island Sunrise - Pet Friendly, Waterfront Duplex! Villa Deep Hole gives access to various tourist sites in the vicinity. More

Along with proximity to Little Oyster Bay, merely 0.7 km away, Sandy Penny | Luxury New Build W/ Water Views, En-Suite Bedrooms + Gourmet Kitchen Retreat Deep Hole villa offers opportunities for mini… More

The 4-bedroom La Dolce Vita - Waterfront With Boat Dock! Deep Hole villa hosts up to 10 guests and is nestled 4.2 km from natural sites such as the Maui Jack's Waterpark. More

Providing guests with an indoor water park and a private garden to ensure a memorable stay, Bayside Haven Villa Deep Hole is just 9 minutes' walk from Little Oyster Bay. This Deep Hole villa features… More

With the capacity to host 7 guests, the 3-bedroom Our Happy Place - Pet Friendly & Waterfront! Deep Hole villa is located about 25 minutes on foot from such significant cultural landmarks as the… More

The 3-bedroom My Island Escape - North Main & Private Dock! Villa Deep Hole accommodates up to 7 guests and offers proximity to the Captain Timothy Hill House, located a mere 0.6 km away. Providing… More

During the stay at One Peace Cottage Deep Hole, guests can indulge in cycling or visit the Chincoteague Pony Centre, located a 15-minute walk away. This villa boasts an indoor water park and a… More

Beach Pines Deep Hole villa is located merely a 12-minute walk from the Museum of Chincoteague and invites guests to join cycling. More

Along with proximity to the Chincoteague Pony Centre, only a 5-minute walk away, Star Of The Sea - Renovated Home Located In Town & Pet Friendly! Deep Hole offers opportunities for mini golf in the… More

The 4-bedroom Avalon - Waterfront Home With Fireplace And Screened Porch Deep Hole offers proximity to nearby tourist spots, such as the Captain Timothy Hill House, situated 3.5 km away. More

With the capacity to host 8 guests, the 4-bedroom Off Belay - Creek View Villa Deep Hole is located around a 10-minute drive from such significant cultural landmarks as the Museum of Chincoteague. More

Located approximately 5 minutes' walk from the Captain Timothy Hill House, Nunzs Cove Villa Deep Hole offers opportunities for cycling in the area. Providing guests with Wi-Fi and private parking… More

Along with proximity to Little Oyster Bay, merely 0.7 km away, Smooth Sailing Villa Deep Hole offers opportunities for cycling in the area. Providing guests with Wi-Fi and private parking, the Deep… More

Saltwater Gospel Villa Deep Hole is located around 20 minutes' walk from Little Oyster Bay and provides cycling for active guests. The accommodation boasts an indoor water park and a private garden… More

To enjoy your vacation in Deep Hole, stay at Assateague Inn 207-S Deep Hole, which is just 1.1 km from the Museum of Chincoteague and within 25 minutes' walk of the Chincoteague Island Library. More

Blue Heron Deep Hole villa is nestled a mere 7 minutes' walk from the Captain Timothy Hill House and can accommodate up to 12 guests. Boasting an indoor water park and a play area, the property is… More

Situated merely a 5-minute walk from the Captain Timothy Hill House, Cozy Nest - Waterview, Pet Friendly, Screened Porch Deep Hole villa is ideal for up to 6 guests. Located 2.1 km from the… More

Joint Venture - Pet Friendly & Water Views! Villa Deep Hole accommodates up to 6 guests and offers proximity to the Chincoteague Pony Centre, located just a 5-minute walk away. More

The 3-bedroom Osprey - Pet Friendly, Fireplace! Deep Hole villa can host up to 6 guests, boasting a convenient location approximately 10 minutes' drive from iconic cultural attractions such as the… More

Windshadow - Waterfront & Pet Friendly! Villa Deep Hole is nestled 9 minutes' walk from the Captain Timothy Hill House and can accommodate up to 8 guests. More

Assateague Inn 106-S Deep Hole is located approximately a 20-minute walk from Little Oyster Bay and offers Wi-Fi for either business or leisure. Offering access to a private pool, this apartment is… More

The 3-bedroom Coastal Cottage - Beachy Oasis In Oyster Bay! Deep Hole hosts up to 8 guests and is nestled approximately a 10-minute ride from natural sites such as the Maui Jack's Waterpark. More

Located only 0.6 km from the Captain Timothy Hill House, The Suncatcher Deep Hole villa offers opportunities for cycling in the area. Providing guests with Wi-Fi and private car parking, this Deep… More

Poole'S Cove - Waterfront; Main Street! Villa Deep Hole is nestled a 5-minute stroll from the Captain Timothy Hill House and can accommodate up to 6 guests. Located 4 km from the historic red-&-white… More

Featuring an outdoor swimming pool, Assateague Inn 213-2R Deep Hole is approximately 300 metres from the Brant. The apartment offers modern facilities, such as Wi-Fi and essentials like private car… More

With the capacity to host 8 guests, the 4-bedroom Dragonfly Point - Waterfront Home W Boat Dock & Deck! Deep Hole is located around a 10-minute ride from such significant cultural landmarks as the… More

House On The Dune Deep Hole villa is situated within 3 km of Little Oyster Bay and provides a Jacuzzi, ensuring a relaxing stay. More

Gray Pearl Villa Deep Hole is located 9 minutes' walk from Little Oyster Bay and offers guests to enjoy cycling. Located 2.7 km from the Chincoteague Island Library, this holiday home provides Wi-Fi… More

Egret'S Cove - Pet Friendly W/ Hot Tub! Villa Deep Hole offers proximity to nearby tourist spots, such as the Chincoteague National Wildlife Refuge, situated 2.7 km away. More

Sunrise View - Waterfront, Kayaks, Gorgeous Sunrises! Villa Deep Hole is located around 25 minutes' walk from the Museum of Chincoteague and provides mini golf and fishing for active guests. More

The 4-bedroom June'S Retreat - Waterfront; Boat Dock! Deep Hole villa hosts up to 10 guests and is nestled nearly a 10-minute drive from natural sites such as the Maui Jack's Waterpark. Located 4.8… More

To enjoy your vacation in Deep Hole, stay at Assateague Inn 107-A Deep Hole, which is 3.9 km from the historic red-&-white Assateague Lighthouse and nearly a 25-minute stroll from the Chincoteague… More

Situated 750 metres from Little Oyster Bay, Blue Moon - Pet Friendly And Great Location! Villa Deep Hole is ideal for up to 8 guests. Located 25 minutes on foot from the Chincoteague Pony Centre, the… More

Paradise View Deep Hole villa is located approximately a 5-minute ride from the Captain Timothy Hill House and provides cycling for active guests. More

Situated only 150 metres from the Captain Timothy Hill House, the 3-bedroom Trembling Bay - Waterfront & A Private Pier! Villa Deep Hole ensures a great leisure experience by offering fishing. More

The 3-bedroom Southern Dream - Water Views & Screened Porch! Deep Hole villa can host up to 8 guests, boasting a convenient location around 25 minutes' walk from iconic cultural attractions such as… More

Assateague Inn 204-S Deep Hole is located just 300 m from the Brant and 3.9 km from the 142 - foot - tall Assateague Lighthouse. Offering access to a private swimming pool, this apartment is a few… More

The 4-bedroom Belle Of The Bay - Beautiful Custom Waterfront Home! Deep Hole offers proximity to such city sites as Oyster Bay, located approximately a 5-minute walk away. More

During the stay at Cedar Cove - Waterfront Home With Fire Pit! Deep Hole, guests can indulge in boating, hiking, and fishing or visit the Museum of Chincoteague, located a 25-minute walk away. The 3… More

At Teal Cottage Deep Hole, guests can enjoy cycling as well as a location just 8 minutes' walk from the Captain Timothy Hill House. Boasting an indoor water park and a private garden, the… More