Deep Hole Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to NT$5,067 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

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
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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.

Find hotels in Piney Island

Deep Hole Hotel Deals

Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
9.8/10 Exceptional! (501 reviews)
Perfect! Adorable, clean, well and nicely appointed — with a view and an affordable price. I’ll be back!

Reviewed on 2026/1/13

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Key West Cottages
Refuge Inn

Refuge Inn

3 out of 5
7058 Maddox Blvd. Chincoteague VA
Fully refundableReserve now, pay when you stay
The price is NT$3,083 per night from Jan 26 to Jan 27
NT$3,083
NT$3,462 total
Jan 26 - Jan 27
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
Comfortable room, pleasant staff, great indoor pool, and easy access to Assateague Island bike paths.

Reviewed on 2026/1/16

Refuge Inn
Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

2.5 out of 5
125 Newtowne Blvd Pocomoke City MD
Fully refundableReserve now, pay when you stay
The price is NT$2,790 per night from Jan 27 to Jan 28
NT$2,790
NT$3,124 total
Jan 27 - Jan 28
includes taxes & fees
8.4/10 Very Good! (886 reviews)
Very very very clean room, floor, furniture, linens, bathroom, everything.

Reviewed on 2025/12/30

Best Western Plus Pocomoke City
See all 709 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.

Frequently asked questions

How much does a Deep Hole vacation package cost?
You can snap up a vacation package to this destination 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?
The off-season is the best time to visit Deep Hole if you're trying to keep costs down. Another tip for finding cheap Deep Hole vacation packages? Try to avoid public holidays and any major events.
How many days is enough for Deep Hole?
Typically, a handful of days is enough to tick off the major attractions during your Deep Hole vacation. However, if you prefer to have time to chill out or take day trips, think about extending your trip.
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. Choose when to get away: Check your schedule and pack your bags. Your preferred season and the activities on offer will also help you decide when to vacation in Deep Hole.
  2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to airfares and activities. Your accommodations will probably be the biggest expense during your trip to Deep Hole.
  3. Work out your trip length: Think about how long you'd like to spend exploring Deep Hole. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your airfare and accommodations: Once you've settled on your dates and duration, lock in the perfect Deep Hole vacation package for you.

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