Deep Hole, VA
Chincoteague
Visit Deep Hole
Things to do
Boat Tours of Chincoteague & Assateague - Wild Ponies
$78
per adult
Chincoteague: Premier Pony & Wildlife Small Group Boat Tour
$79
per adult
100% of travellers recommend
Chincoteague and Assateague Island Boat Tour with Capt. John
$95
per adult
Chincoteague: Guided Sunset Kayak Tour with Wildlife Views
$75
per adult
Chincoteague & Assateague Small-Group Sunset Boat Tour
$89
per adult
Chincoteague and Assateague Birdwatching Boat Tour
$89
per adult
100% of travellers recommend
Deep Hole Hotel Deals
Oyster Catcher | Deep Creek Waterfront w/ Deep Water Dock, Screened Porch, Guest Cottage & Pets
Chincoteague Island VA
Stay at this vacation home in Chincoteague. Enjoy a water park, laundry facilities, and cable/satellite TV service. Popular attractions Captain Timothy Hill ...
9/10 Wonderful! (6 reviews)
"Old and lovely house, great dock, pets allowed, kayaking access, roomy parking. We love Oyster Catcher!"
Reviewed on Sep 5, 2026
Escape at Deep Hole Hideaway | Chic 2BR Retreat w/ Full Kitchen, Daybed + Sleeper Sofa, Pet Friendly
Chincoteague Island VA
Stay at this vacation home in Chincoteague. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Captain Timothy Hill ...
9/10 Wonderful! (6 reviews)
"Cozy and hidden away from the main road. Plenty of room for dogs to roam around."
Reviewed on Jul 13, 2026
Cozy 2-bedroom house in Chincoteague
Chincoteague VA
$269 nightly
The price is $302 total per night from Oct 4 to Oct 5
$302 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this vacation home in Chincoteague. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Maui Jack's Waterpark and Museum of Chincoteague ...
10/10 Exceptional! (6 reviews)
"The cottage is adorable and the owners are superb! The house was super clean, well-appointed, and in a very quiet area. I would gladly stay her again.pros:quiet well stocked kitchenwasher/dryernice tub/showercomfy bedsgreat ownerslot of thick towels and pillowscons:mosquitoes! (nothing the owner ..."
Reviewed on Aug 7, 2026
Quaint Cottages Near Everything on Beach Road
Chincoteague VA
Stay at this vacation home in Chincoteague. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Maui Jack's Waterpark and Museum of ...
9.2/10 Wonderful! (46 reviews)
"Jay was there to greet us, the place was very clean. It is walking distance to town."
Reviewed on Sep 9, 2026
Sunrise Shore | Waterfront Oyster Bay Home w/ Pool, Hot Tub, Panoramic Views & Modern Luxury
Chincoteague Island VA
Stay at this vacation home in Chincoteague. Enjoy private pools, a water park, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (38 reviews)
"Over priced, neglected, on going problems that haven’t been addressed,"
Reviewed on Aug 6, 2026
Joint Venture | Walk to Maddox Blvd, Water Views, Affordable Stay + Pet Friendly
Chincoteague Island VA
Stay at this vacation home in Chincoteague. Enjoy a water park, laundry facilities, and balconies. Popular attractions Maui Jack's Waterpark and Museum of Chincoteague ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Where to stay in Deep Hole
Find the best Deep Hole areas and neighborhoods for the activities you enjoy most.
Photo by Michael Gibson
Open Photo by Michael Gibson
Downtown Chincoteague
While visiting Downtown Chincoteague, you might make a stop by sights like Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.
Piney Island
While visiting Piney Island, you might make a stop by sights like Maui Jack's Waterpark and Museum of Chincoteague.
Snotty Ridge
While there might not be top attractions in Snotty Ridge, you can explore the larger area and discover places like Robert N. Reed Downtown Waterfront Park and Assateague Point.
Down the Marsh
If you're looking for some top things to see and do in Down the Marsh and surrounding area, you can visit Robert N. Reed Downtown Waterfront Park and Assateague Point.
Birch Town
While Birch Town isn't home to many top sights, Maui Jack's Waterpark and Museum of Chincoteague are some notable places to visit nearby.
