Deep Hole Vacations from $320
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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.
The Colony at Virginia Beach
Northeast Virginia Beach
Save 100% on your flight
Price was $662, price is now $458 per person
$458
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8/10 Very Good! (6 reviews)
Other than a “one bug” citing, the property is very dated but clean. Beds and linens are great. Nothing better than listening to the crashing waves as you sleep.
Reviewed on Dec 27, 2025
Boardwalk Resort and Villas
Northeast Virginia Beach
Price was $494, price is now $343 per person
$343
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.6/10 Excellent! (1,003 reviews)
Great room was a blast for the kids to play in thebpool and hot tub as well.
Reviewed on Dec 30, 2025
Hilton Norfolk The Main
Downtown Norfolk
Save 100% on your flight
Price was $1,338, price is now $972 per person
$972
per person
Mar 23 - Mar 27
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
9/10 Wonderful! (1,000 reviews)
We’ve stayed here three times already and we really love it. The location is excellent, and having convenient restaurants inside the hotel makes everything so easy. Our favorite restaurants are Saltines and Grain. We definitely recommend this hotel, and of course, we would absolutely stay here again. We’ve stayed here three times already and we really love it. The location is excellent, and having convenient restaurants inside the hotel makes everything so easy. Our favorite restaurants are Saltines and Grain. We definitely recommend this hotel, and of course, we would absolutely stay here again.
Reviewed on Dec 28, 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 VA
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
Quaint Cottages Near Everything on Beach Road
Chincoteague VA
9.4/10 Exceptional! (40 reviews)
Loved this cute place Nothing fancy but perfectly functional for a 2 night stay and close to everything I came for! Communication was over the top outstanding! A storm was coming in and the owner kept me updated! Also recommended some local events going on. I'm already planning on coming back!
Reviewed on Oct 12, 2025
Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes, Spend Christmas
Chincoteague VA
9.8/10 Exceptional! (17 reviews)
Perfect accommodation. Kitchen was fully stocked to cook in and everything was exceptionally clean.
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.