Extended Stay 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

Featuring island tours to make your visit more entertaining, Escape At Deep Hole Hideaway - Pet Friendly Duplex! Villa is a 9-minute walk from Deep Hole Creek. The 2-bedroom holiday home hosts up to… More

Offering an aqua park and a golf course for guests' leisure, the 3-bedroom Slack Tide Deep Hole villa is situated about a 25-minute walk from Chincoteague Veteran's Memorial Park. Offering island… More

Bayside Bliss | Chincoteague Waterfront W/ Dock, Enclosed Porch Dining, Sunset Views & 4Br Comfort Deep Hole villa hosts up to 10 guests and is nestled approximately a 10-minute ride from natural… More

The 36 m² Assateague Inn 110-S Deep Hole is located a mere 0.7 km from Maui Jack's Waterpark and about a 5-minute walk from The Brant Gift Shop. This 1-bedroom apartment has an outdoor swimming pool,… More

The 4-bedroom Shore Thing On Oyster Bay - Waterfront, Boat Dock! Deep Hole villa hosts up to 8 guests and is nestled within 3 km of natural sites such as Maui Jack's Waterpark. Located around a 10… More

Offering a location about 25 minutes' walk from Chincoteague National Wildlife Refuge, the 4-bedroom Wildcat Retreat - Waterfront & Phenomenal Views! Villa Deep Hole gives access to various tourist… More

Nestled 2.3 km from Chincoteague Pony Centre, the 3-bedroom Sunshine Daydream - Pet Friendly & Waterfront View! Villa Deep Hole entices guests to explore various tourist destinations nearby. Offering… More

Situated nearly a 25-minute walk from Chincoteague Pony Centre, the 4-bedroom Carriage House Villa Deep Hole offers guests to enjoy an aqua park and a golf course. The holiday home features… More

The 3-bedroom Coastal Retreat Villa Deep Hole is nestled merely 9 minutes' walk from Little Oyster Bay and can accommodate up to 8 guests. Located 3.8 km from Veteran's Memorial Park, the villa comes… More

Staying at the 3-bedroom Caribbean Ketch Villa Deep Hole, guests can visit Piney Island, which is only 0.6 km away. Offering island tours, the Deep Hole villa can accommodate up to 8 people. More

Situated 4.9 km from Chincoteague Veteran's Memorial Park, the 4-bedroom Hidden Treasure - Waterfront Home With Boat Dock! Deep Hole entices guests to explore various tourist attractions in the area.… More

Staying at the 3-bedroom The Robinson Family Beach House Deep Hole villa, guests can visit Museum of Chincoteague, which is nearly a 25-minute walk away. Offering island tours, the Deep Hole holiday… More

Staying at Grey Heron - Pet Friendly, Waterfront Home With Boat Dock! Deep Hole, guests can easily reach Chincoteague Island Library, located nearly a 25-minute walk away. Offering island tours, this… More

Featuring island tours to make your visit more entertaining, Castlebar - Luxury Waterfront Home With Private Dock! Deep Hole is 10 minutes' drive from Museum of Chincoteague. The 5-bedroom villa… More

Located around 5 minutes' walk from Museum of Chincoteague, Shackeau East Villa Deep Hole offers cycling to diversify guests' leisure. The 1-bedroom and 1-bathroom villa boasts an aqua park and a… More

The 4-bedroom Heron'S Cove On Salt Meadow | Bayfront Views, Dock, King Suites, Fireplace + Pet Friendly Deep Hole villa is located around 25 minutes' walk from Museum of Chincoteague, giving access… More

Staying at the 4-bedroom Oyster Catcher - Pet Friendly & Deep Water Access! Deep Hole villa, guests can visit Deep Hole Creek, which is only 0.7 km away. Offering island tours, the Deep Hole holiday… More

The 2-bedroom Egret'S Walk | Peaceful Marsh & Creek View Cottage North Of Town W/ Wildlife Views & Pet Friendly Deep Hole hosts up to 5 guests and provides proximity to Captain Timothy Hill House… More

Featuring island tours to make your visit more entertaining, Lazy Days - Pet Friendly With Screened Gazebo! Deep Hole villa is 25 minutes' walk from Maui Jack's Waterpark. The 3-bedroom holiday home… More

The 4-bedroom Grandview - Pet Friendly, Waterfront Home With Dock! Deep Hole is located around 25 minutes' walk from Chincoteague National Wildlife Refuge, giving access to various tourist spots… More

The 36 m² Assateague Inn 111-2R Deep Hole is located 3.9 km from the 142 - foot - tall Assateague Lighthouse and about a 25-minute walk from Veteran's Memorial Park. Set steps away from The Brant… More

The 3-bedroom Langtree - Pet Friendly, Waterfront With Boat Dock! Villa Deep Hole hosts up to 10 guests and is nestled within 25 minutes' walk of natural sites such as Maui Jack's Waterpark. Located… More

Offering a location nearly a 25-minute walk from Chincoteague Veteran's Memorial Park, the 2-bedroom An Unfettered View | Wheelchair Accessible Oyster Bay Waterfront Ranch W/ Long Pier For Crabbing… More

Staying at the 4-bedroom Charlotte'S Morning Sun | Luxury Oyster Bay Waterfront W/ Unobstructed Views, Screened Porch & Dock Deep Hole villa, guests can visit Little Oyster Bay, which is only 1.3 km… More

Featuring island tours to make your visit more entertaining, the 4-bedroom Wildcat Haven - Waterfront & Phenomenal Views! Villa Deep Hole is about 6 km from the 142 - foot - tall Assateague… More

The 2-bedroom Homestead - Located On Main Street With Outdoor Shower! Deep Hole villa is nestled only a few steps from Captain Timothy Hill House and can accommodate up to 5 guests. Located about 4… More

Nestled about 20 minutes' walk from 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 Catch Of The Day Villa Deep Hole accommodates up to 6 guests and offers proximity to Little Oyster Bay, located just 0.7 km away. This Deep Hole holiday home boasts an aqua park and a… More

Offering an aqua park and a golf course for guests' leisure, the 3-bedroom The Happy Crab Villa Deep Hole is situated around a 25-minute walk from Captain Timothy Hill House. This villa features… More