Deep Hole Vacations from $323

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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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,003 reviews)
I liked everything. No complaints

Reviewed on Aug 11, 2025

Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
per person
Nov 6 - Nov 9
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
No reviews
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,760 reviews)
Just wish it was more convenient for dinning an bars

Reviewed on Aug 9, 2025

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
6/10 (641 reviews)
2 minutes easy walk to the Boardwalk at the Gorgeous Beach

Reviewed on Jun 26, 2025

Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,649 reviews)
I liked that Watermans was right beside it, they have amazing food. Didnt like that we had to keep messing with toilet because most of the time it wouldn't fill back up with water.

Reviewed on Aug 10, 2025

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Deep Hole Hotel Deals

Quaint Cottages Near Everything on Beach Road

Quaint Cottages Near Everything on Beach Road

Chincoteague
9.4/10 Exceptional! (36 reviews)
Last minute
"We booked this at the very last minute so we could clean out our father’s home (he passed the week before). It was perfect for our needs. One caution…the grass has tiny little burrs that stick to socks and flip flops. Nothing to do about them but if you have a dog, check their paws. We were even ..."

Reviewed on Sep 29, 2024

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Quaint Cottages Near Everything on Beach Road
An Unfettered View - Beautiful ranch w/ boat dock!

An Unfettered View - Beautiful ranch w/ boat dock!

Chincoteague Island
Fun without sun.
"Even with the wind and rain we had a great time."

Reviewed on Jun 27, 2023

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An Unfettered View - Beautiful ranch w/ boat dock!
Oyster Bay Hideaway on Chincoteague Island!

Oyster Bay Hideaway on Chincoteague Island!

Chincoteague Island
10/10 Exceptional! (9 reviews)
Really nice back view
"I stayed for Pony Swim. It was beautiful overlooking marsh and very convenient"

Reviewed on Aug 5, 2025

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Oyster Bay Hideaway on Chincoteague Island!
See all 742 properties in Deep Hole
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.

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Frequently asked questions

How much does a Deep Hole vacation package cost?
You can snap up a vacation package to this destination from $323 on Expedia. But how much your vacation to Deep Hole costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Deep Hole?
October, November and December are the best times to look for cheap Deep Hole vacation packages. Traveling in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Deep Hole?
With a well-organized schedule, you can easily tick off the most popular Deep Hole attractions in a handful of days. But if you'd like to discover lesser-known spots or go on day trips, consider booking your Deep Hole vacation for longer.
How to find the best Deep Hole package deals?
Use Expedia's filter tool to find some of the best Deep Hole package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Deep Hole package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Deep Hole vacation as a package?
You can enjoy significant savings on your next Deep Hole retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Deep Hole?
If you're planning a spur-of-the-moment Deep Hole trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Deep Hole?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Deep Hole.
  2. Plan your budget wisely: In addition to the cost of your hotel, you'll need to factor in other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that could crop up during your trip to Deep Hole.
  3. Organize your Deep Hole escape with our trip planning tool: Look for and book hotels and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Deep Hole together.
  4. Decide how long to go for: Now that you're up to speed on Deep Hole, you can work out the perfect length of your break. Put together a draft plan and give yourself enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalized Deep Hole vacation package.
  6. Add on experiences and excursions: Have a look at our dedicated travel guide to find some incredible things to do in Deep Hole in Deep Hole. Book tickets or make reservations before you go to save time and avoid the stress of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Deep Hole vacation packages?
Your Deep Hole break should be an escape from your daily routine, not a source of money worries. So to allow you extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.