Deep Hole Travel Guide
Tourist Guide
Visit Deep Hole
Activities
Boat Tours of Chincoteague & Assateague - Wild Ponies
NZ$130
per adult
Kayak Tour along Assateague & Chincoteague Island, Virginia
NZ$125
per adult
Chincoteague's Kayak Tour around the Islands
NZ$149
per adult
Guided Kayak Tour to see ponies, birds, dolphins and more
NZ$125
per adult
100% of travellers recommend
Famous Chincoteague Island Pony Cruise with Expert Narration
NZ$99
per adult
100% of travellers recommend
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 ...
9.2/10 Wonderful! (5 reviews)
"Pros-great location, great views from screened in back porch, loved the dock outback. The guest cottage is quite lovely.Cons-the house needs attention. Broken bed first floor, blinds in some rooms won’t go up, front door handle broken off so we never opened, holes in the screen porch, bathroom blind ..."
Reviewed on 2 Aug 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 ...
8.6/10 Excellent! (38 reviews)
"Over priced, neglected, on going problems that haven’t been addressed,"
Reviewed on 6 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! (44 reviews)
"The pros of this property:Location is great, and there is even a cut through to get to a bunch of the attractions on the main drag.The host was responsive and even shipped a shirt we left behind.It was affordable, even during the peak season.The cons:Check-in was confusing and we walked in on other ..."
Reviewed on 11 Aug 2026
Cozy 2-bedroom house in Chincoteague
Chincoteague VA
The price is NZ$536 per night from 8 Sept to 9 Sept
NZ$536
per night
8 Sept - 9 Sept
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
Pond Front - Tons of Wildlife!
Chincoteague Island VA
Stay at this holiday home in Chincoteague. Enjoy free Wi-Fi, a water park and a garden. Popular attractions Captain Timothy Hill House and Oyster Bay are located ...
10/10 Exceptional! (1 review)
"This is a beautiful property and the hosts have made sure to anticipate even need and provide accordingly. The house provides a great place for a family with grandparents to stay for a week. There are many places just to sit down and enjoy the view and the kitchen is well stocked to prepare meals. ..."
Reviewed on 12 Aug 2026
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 Chincoteague Channel.
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 Assateague Lighthouse.
