Deep Hole Vacations from $411
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Your Deep Hole Vacation
Take the stress out of organizing your next exciting adventure with a Deep Hole vacation package. Whether you've come for its history, food or something else, there's an inexhaustible array of experiences to be had. Fill your itinerary with tours of Maui Jacks Waterpark, Robert N. Reed Downtown Waterfront Park and Oyster Bay, some of the things you shouldn't miss during your trip to Deep Hole. Browse Expedia's wide range of travel options and book your dream vacation to Deep Hole today.
The Latest Deep Hole Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pamlico Station Edgecamp
Save 100% on your flight
Price was $776, price is now $411 per person
$411
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (18 reviews)
The hotel was perfect and spacious. The only thing was when it rained 🌧 🙃 we got wet to the entrance to our room because of the location...maybe adding a overhang to help with not getting wet.
Reviewed on Oct 12, 2025
Ocean 27
Northeast Virginia Beach
Save 100% on your flight
Price was $2,440, price is now $1,603 per person
$1,603
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
6.4/10 (1,116 reviews)
Close to beach. Ground level beach access rooms. Grounds need to be picked-up a bit. Centrally located along boardwalk.
Reviewed on Oct 13, 2025
The Sanderling
Save 100% on your flight
Price was $778, price is now $545 per person
$545
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (519 reviews)
It was a nice stay though the room was not what you would expect at the price point. Two of the walls were in need of repairs, windows needed some cleaning, coffee in room was a kettle with tea like bags of coffee that tasted awful, and bathroom had pretty much nothing in it.
Reviewed on Oct 25, 2025
The Atrium Resort, Virginia Beach by Vacatia
Northeast Virginia Beach
Save 100% on your flight
Price was $806, price is now $565 per person
$565
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
8.2/10 Very Good! (1,476 reviews)
We love the homey feeling of the room. The whole apartment aka hotel room was the best. Can't wait to cone back during the warmer season. Thanks for making my birthday
Reviewed on Oct 12, 2025
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.
Deep Hole Hotel Deals
The Blue Crab - Your Dream Vacation awaits you!
Chincoteague Island
9.8/10 Exceptional! (14 reviews)
This was the perfect house for us! We enjoyed the one floor living, the large kitchen and counter space was more than sufficient. The linens and towels were provided which was one less thing to have to pack. We enjoyed being close to town and all the restaurants, the park, and the beach. Communication ...
Reviewed on Oct 23, 2025
Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes,Oct discounts ask
Chincoteague
9.8/10 Exceptional! (16 reviews)
Perfect accommodation. Kitchen was fully stocked to cook in and everything was exceptionally clean.
Reviewed on Oct 12, 2025
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!
Chincoteague
$331 nightly
The price is $372 total per night from Nov 15 to Nov 16
$372 total
Nov 15 - Nov 16
Total with taxes and fees
9.4/10 Exceptional! (13 reviews)
The home was perfect for our family gathering.
Reviewed on Oct 12, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.