Deep Hole Vacations from $391
Book a Hotel + Flight or Car together to unlock savings
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 Sanderling
Save 100% on your flight
Price was $1,328, price is now $825 per person
$825
per person
May 16 - May 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (523 reviews)
The elevator was broken. We were told that had been struck by lightning. I was also told that it had been broken for one year. They have three floors almost 2 of the buildings and I think two on the other, but I don’t know if they meant elevators in the building that we were in or every single one wasn’t clarified also told that they were having a New Year’s Eve celebration. Nothing was held in the lobby as previously expected the restaurant on site closed at 9 PM New Year’s Eve and we were rushed like you wouldn’t believe for six course meal that cost $300.
Reviewed on Jan 7, 2026
Pamlico Station Edgecamp
South Rodanthe
Save 100% on your flight
Price was $1,138, price is now $749 per person
$749
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
9.4/10 Exceptional! (19 reviews)
beautiful room with very responsive concierge
Reviewed on Jan 15, 2026
The Ocean Key Virginia Beach Resort
Northeast Virginia Beach
Save 100% on your flight
Price was $724, price is now $486 per person
$486
per person
Apr 7 - Apr 12
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
7.8/10 Good! (1,448 reviews)
not a good view and resturant across the street has deliveries and customers of all hours! Bedroom door to balcony would not close all the way. If you need a budget stay...... otherwise skip it!
Reviewed on Feb 24, 2026
Inn at Perry Cabin
Downtown St. Michaels
Save 100% on your flight
Price was $1,710, price is now $1,156 per person
$1,156
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.6/10 Exceptional! (369 reviews)
Friendly and attentive staff, good cleaning services
Reviewed on Oct 26, 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
Sunrise Shore - Waterfront; Private pool & hot tub!
Chincoteague Island VA
8.8/10 Excellent! (34 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 Jul 17, 2025
Oyster Catcher - Pet friendly; Deep water access!
Chincoteague Island VA
10/10 Exceptional! (4 reviews)
Sunrise views from the porch were breathtaking.
Reviewed on Sep 30, 2025
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
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.