Holiday Homes in Deep Hole

Located about 10 minutes' drive from Chincoteague Pony Centre, the 4-bedroom La Dolce Vita - Waterfront With Boat Dock! Deep Hole villa provides access to various tourist attractions in the vicinity.… More

The 2-bedroom Bayside Haven Villa Deep Hole is located approximately 25 minutes' walk from Chincoteague Island Library and welcomes its guests to enjoy cycling. Offering island tours, the property… More

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

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

Suitable for 8 guests, One Peace Cottage Deep Hole offers a location a 6-minute walk from Deep Hole Creek and features an aqua park and a golf course. Located 2.1 km from Maui Jack's Waterpark, the 3… More

Offering an aqua park and a golf course for guests' leisure, Beach Pines Deep Hole villa is situated 2.9 km from Little Oyster Bay. This 3-bedroom holiday home features opportunities for cycling in… More

Along with proximity to Chincoteague Pony Centre, only a 5-minute walk away, the 3-bedroom Star Of The Sea - Renovated Home Located In Town & Pet Friendly! Deep Hole offers opportunities for mini… More

Situated 3.5 km from Captain Timothy Hill House, the 4-bedroom Avalon | Oyster Bay Waterfront Home W/ Gas Fireplace, Cathedral Ceilings & Massive Screened Porch Deep Hole provides access to numerous… More

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

At the 4-bedroom Nunzs Cove Villa Deep Hole, guests can enjoy cycling as well as a location nearly 5 minutes' walk from Captain Timothy Hill House. Boasting an aqua park and a golf course, the… More

Along with proximity to Little Oyster Bay, merely 0.7 km away, the 3-bedroom Smooth Sailing Villa Deep Hole offers opportunities for cycling in the area. Providing guests with Wi-Fi and a private… More

Located around 5 minutes' walk from Chincoteague Pony Centre, the 2-bedroom Saltwater Gospel Villa Deep Hole offers cycling to diversify guests' leisure. This property boasts an aqua park and a golf… More

The 3-bedroom Blue Heron Deep Hole villa is located just 7 minutes' walk from Captain Timothy Hill House and invites guests to enjoy island tours. The property features opportunities for mini golf… More

Featuring island tours to make your visit more entertaining, Cozy Nest - Waterview, Pet Friendly, Screened Porch Deep Hole villa is 25 minutes' walk from Chincoteague Pony Centre. The 2-bedroom… More

Joint Venture - Pet Friendly & Water Views! Villa Deep Hole, located nearly 5 minutes' walk from The Brant Gift Shop, can host up to 6 guests. Providing guests with Wi-Fi and parking, this Deep Hole… More

Staying at the 3-bedroom Osprey - Pet Friendly, Fireplace! Deep Hole villa, guests can visit Chincoteague Pony Centre, which is nearly 10 minutes' drive away. Offering island tours, this Deep Hole… More

Featuring island tours to make your visit more entertaining, Windshadow - Waterfront & Pet Friendly! Villa Deep Hole is 25 minutes' walk from Maui Jack's Waterpark. The 3-bedroom holiday home hosts… More

The 3-bedroom Coastal Cottage - Beachy Oasis In Oyster Bay! Deep Hole hosts up to 8 guests and is nestled nearly a 10-minute drive from natural sites such as Maui Jack's Waterpark. Located 2.8 km… More

Located nearly 25 minutes' walk from Chincoteague Pony Centre, the 4-bedroom The Suncatcher Deep Hole villa provides access to various tourist attractions in the vicinity. This Deep Hole holiday home… More

Poole'S Cove | Waterfront Main Street Retreat Fully Renovated W/ Rooftop Lounge & Artistic Charm Deep Hole villa is located 5 minutes' walk from Captain Timothy Hill House and invites guests to enjoy… More

The 4-bedroom Dragonfly Point - Waterfront Home W Boat Dock & Deck! Deep Hole is located approximately a 10-minute drive from Veteran's Memorial Park and provides canyoning for active guests. More

The 3-bedroom House On The Dune Deep Hole villa is nestled within 3 km of Little Oyster Bay and provides a Jacuzzi. More

Gray Pearl Villa Deep Hole is located 9 minutes' walk from Little Oyster Bay and entices guests with an aqua park and a golf course. The 4-bedroom holiday home features opportunities for cycling in… More

Situated 10 minutes' drive from Chincoteague National Wildlife Refuge, Egret'S Cove | Bayfront Oyster Bay Retreat W/ Hot Tub, Screened Porch, Dock & Fenced Yard For Pets Deep Hole villa provides… More

The 3-bedroom Sunrise View - Waterfront, Kayaks, Gorgeous Sunrises! Villa Deep Hole is located around 25 minutes' walk from Museum of Chincoteague and provides mini golf and fisheries for active… More

The 4-bedroom June'S Retreat | Luxury Waterfront Estate W/ Panoramic Bay Views, Boat Dock, Billiards + Verandas Deep Hole villa can host up to 10 guests, boasting a prime location nearly a 10-minute… More

Blue Moon - Pet Friendly And Great Location! Villa Deep Hole is nestled 750 metres from Little Oyster Bay and can accommodate up to 8 guests. Located 25 minutes' stroll from Chincoteague Pony Centre,… More

The 4-bedroom Paradise View Deep Hole villa is located approximately a 5-minute ride from Captain Timothy Hill House and provides cycling for active guests. The Deep Hole holiday home boasts an aqua… More

The 2-bedroom Trembling Bay - Waterfront & A Private Pier! Villa Deep Hole hosts up to 6 guests and provides proximity to Captain Timothy Hill House, situated merely 150 metres away. Providing guests… More

Accommodating up to 8 guests, the 2-bedroom Southern Dream - Water Views & Screened Porch! Deep Hole villa is situated approximately 25 minutes' walk from renowned cultural sites such as Chincoteague… More

The 3-bedroom Teal Cottage Deep Hole accommodates up to 10 guests and offers proximity to Captain Timothy Hill House, located just an 8-minute walk away. The holiday home boasts an aqua park and a… More

During the stay at Vineyard Cove Villa Deep Hole, guests can indulge in cycling or visit Chincoteague National Wildlife Refuge, located 25 minutes' walk away. The 3-bedroom holiday home boasts an… More

Up to 8 guests can stay at Crabby Pines - Pet Friendly Modern Accommodations! Deep Hole villa and enjoy Deep Hole Creek, located about 5 minutes' walk away. Located 2.3 km from Captain Timothy Hill… More