Deep Hole Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.

Top Deep Hole Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sahara Motel
Beach Walk
Empress Motel
White Marlin Inn
OCHG OF Villas

Ready to book your vacation to Deep Hole?

 

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Deep Hole Hotel Deals

Quaint Cottages Near Everything on Beach Road

Quaint Cottages Near Everything on Beach Road

Chincoteague
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

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

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! (8 reviews)
Great spot and location
"Great place for a family to stay to explore Chincoteague, the place comes as advertised and would recommend for a future visit."

Reviewed on Jun. 23, 2025

Oyster Bay Hideaway on Chincoteague Island!
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

How much does a Deep Hole vacation package cost?
You'll find cheap prices from CA $1,312 on Expedia for your Deep Hole getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Deep Hole costs.
What are the cheapest months to go to Deep Hole?
Travel in the off-peak season and you're likely to score cheap Deep Hole vacation packages. Remember that public holidays and major events and festivals can have an impact on prices, so do a little research before booking.
How many days is enough for Deep Hole?
Usually, a handful of days is enough to check out the main sights during your Deep Hole vacation. But if you'd like to have some time to rest or take day tours, think about extending your itinerary.
How to find the best Deep Hole package deals?
Bagging a cheap Deep Hole package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Deep Hole package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Deep Hole vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Deep Hole vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Deep Hole?
Enjoy amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Deep Hole trip.
How to plan a trip to Deep Hole?

  1. Choose when to get away: Check your diary and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to visit Deep Hole.
  2. Set your budget: Factor in costs such as transportation, flights and meals when working out how much to save for your trip to Deep Hole. Then, select a hotel that matches your budget, whether that's an affordable option or a lavish getaway.
  3. Set the duration of your trip: Start by listing all the activities and attractions you want to experience in Deep Hole. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Deep Hole vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.