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 Birdwatching Boat Tour
$89
per adult
100% of travellers recommend
Chincoteague & Assateague Small-Group Sunset Boat Tour
$89
per adult
Chincoteague's and Assateague’s Grand Boat Tour with Capt.John
$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 ...
9.2/10 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 Aug 2, 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! (37 reviews)
"This was our final stay. The furniture is gross, the beds are broken, one had bugs that my teen grandaughter had more bites all over her body each morning! The drains are clogged all the time.Kitchen had Rat Poison in the FOOD Pantry!Kitchen drain was clogged all the time & made it difficult to even ..."
Reviewed on Jul 16, 2026
Pond Front - Tons of Wildlife!
Chincoteague Island VA
Stay at this vacation home in Chincoteague. Enjoy free WiFi, 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 Aug 12, 2026
Cozy 2-bedroom house in Chincoteague
Chincoteague VA
$280 nightly
The price is $314 total per night from Sep 15 to Sep 16
$314 total
Sep 15 - Sep 16
Total with taxes and fees
Stay at this vacation home in Chincoteague. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Chincoteague National Wildlife Refuge and ...
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
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
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 Chincoteague National Wildlife Refuge ...
9.4/10 Exceptional! (43 reviews)
"This property was not as clean as previous reviews had mentioned. It was missing basic items such as spoons (none at all), a sponge, and a complete roll of paper towels. We had to buy these things as well as cleaning supplies because the floors were so dirty. Smoke alarms were missing batteries and ..."
Reviewed on Jul 23, 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.
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 Chincoteague Channel.
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.
