
Deep Hole Holidays
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Your Deep Hole Holiday
When a getaway to the city is calling, answer it with a holiday package to Deep Hole. With all your travel needs in order before you leave, all you have to do here is focus on having a ball. Like to explore your new surroundings? Maui Jacks Waterpark, Robert N. Reed Downtown Waterfront Park and Oyster Bay are just three of the top-rated places to visit during a trip to Deep Hole. A couple of clicks is all it takes to craft your dream Deep Hole holiday on Expedia.
Our guide on where to stay in Deep Hole
Find the best Deep Hole areas and neighborhoods for the activities you enjoy most. Learn more about Deep Hole

Piney Island
2 out of top 10 points of interest in this area
While visiting Piney Island, you might make a stop by sights like Maui Jack's Waterpark and Museum of Chincoteague.
Our pick of the best Deep Hole Hotel Deals

Sunrise Shore - Waterfront; Private pool & hot tub!
Chincoteague Island
9/10 Wonderful! (15 reviews)
"We Loved Staying at Sunrise Shore ! The view from inside the Home is so much better then the pictures !! Our Family/Grandchildren had a Wonderful time in the Pool and the Jacuzzi is very much a Great Perk !"
Reviewed on 17 July 2025

The Blue Crab - Your Dream Vacation awaits you!
Chincoteague Island
9.6/10 Exceptional! (12 reviews)
"The Blue Crab was perfect for our family vacation. It was beautiful, clean, spacious, and had everything we needed to enjoy our stay. If we come back, we’ll be staying at The Blue Crab again!"
Reviewed on 22 July 2025

Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes, fall rates
Chincoteague
9.8/10 Exceptional! (16 reviews)
"Perfect accommodation. Kitchen was fully stocked to cook in and everything was exceptionally clean."
Reviewed on 12 Oct 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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.