Deep Hole Travel Guide
Tourist Guide
Visit Deep Hole
Activities
Kayak Tour along Assateague & Chincoteague Island, Virginia
NZ$131
per adult
Boat Tours of Chincoteague & Assateague - Wild Ponies
NZ$136
per adult
Chincoteague's Up The Bay Pony and Wildlife Tour by Boat
NZ$138
per adult
94% of travellers recommend
Sunset Wildlife Cruise along Assateague & Chincoteague Island
NZ$115
per adult
100% of travellers recommend
Chincoteague and Assateague Island Boat Tour with Capt. John
NZ$166
per adult
Our pick of the best Deep Hole Hotel Deals
Oyster Catcher | Deep Creek Waterfront w/ Deep Water Dock, Screened Porch, Guest Cottage & Pets
Chincoteague Island VA
Stay at this holiday home in Chincoteague. Enjoy a water park, laundry facilities and cable/satellite TV service. Popular attractions Captain Timothy Hill House ...
9/10 Wonderful! (6 reviews)
"Old and lovely house, great dock, pets allowed, kayaking access, roomy parking. We love Oyster Catcher!"
Reviewed on 5 Sept 2026
Cozy 2-bedroom house in Chincoteague
Chincoteague VA
The price is NZ$532 per night from 16 Oct to 17 Oct
NZ$532
16 Oct - 17 Oct
includes taxes & fees
Stay at this holiday home in Chincoteague. Enjoy free Wi-Fi, 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 7 Aug 2026
Escape at Deep Hole Hideaway | Chic 2BR Retreat w/ Full Kitchen, Daybed + Sleeper Sofa, Pet Friendly
Chincoteague Island VA
Stay at this holiday home in Chincoteague. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Captain Timothy Hill House ...
9/10 Wonderful! (6 reviews)
"Cozy and hidden away from the main road. Plenty of room for dogs to roam around."
Reviewed on 13 July 2026
Quaint Cottages Near Everything on Beach Road
Chincoteague VA
Stay at this holiday home in Chincoteague. Enjoy free Wi-Fi, patios and cable/satellite TV service. Popular attractions Maui Jack's Waterpark and Museum of Chincoteague ...
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 9 Sept 2026
Sunrise Shore | Waterfront Oyster Bay Home w/ Pool, Hot Tub, Panoramic Views & Modern Luxury
Chincoteague Island VA
Stay at this holiday home in Chincoteague. Enjoy private pools, a water park and laundry facilities. Our guests praise the helpful staff in their reviews. Popular ...
Southern Dream | Oyster Bay Water View Home, Screened Porch, Large Deck + Outdoor Shower
Chincoteague Island VA
Stay at this holiday home in Chincoteague. Enjoy a water park, patios and cable/satellite TV service. Popular attractions Maui Jack's Waterpark and Museum of ...
9/10 Wonderful! (26 reviews)
Quiet Location with a View
"Great house and location is close enough to the main drag but far enough away to have absolute quiet at night. Rooms were fine. Kitchen had everything you need... However, Dishwasher was broken... informed office... they said they were working on it... Asked for extra dish towels and a drying rack ..."
Reviewed on 30 July 2025
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.
Our guide on where to stay in Deep Hole
Find the best Deep Hole areas 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
Snotty Ridge might not have many top sights, but Robert N. Reed Downtown Waterfront Park and Assateague Point are two attractions nearby that you can check out.
Down the Marsh
While there might not be top attractions in Down the Marsh, you can explore the larger area and discover places like Robert N. Reed Downtown Waterfront Park and Assateague Point.
Birch Town
Though Birch Town may not have many top sights, you can venture to the surrounding area to see attractions like Maui Jack's Waterpark and Museum of Chincoteague.
