Deep Hole Vacations

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    Save up to ₩234,741 when you book a flight and hotel together*
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Deep Hole Hotel Deals

Waterside Inn

Waterside Inn

2 out of 5
3761 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is ₩87,151 per night from Oct 26 to Oct 27
₩87,151
₩97,871 total
Oct 26 - Oct 27
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"The staff was very helpful and accommodating. The room, view and overlook of the bay was both restful and easy on the eye. I would have liked to have had 2 luggage holders as well as screens on the doors. We would definitely stay there on our next trip to the area."

Reviewed on Oct 7, 2025

Waterside Inn
Marina Bay Hotel & Suites, an Ascend Collection Hotel

Marina Bay Hotel & Suites, an Ascend Collection Hotel

2.5 out of 5
3801 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is ₩95,625 per night from Oct 26 to Oct 27
₩95,625
₩128,747 total
Oct 26 - Oct 27
includes taxes & fees
9/10 Wonderful! (992 reviews)
"Has all of the basics plus a great pool and view"

Reviewed on Oct 5, 2025

Marina Bay Hotel & Suites, an Ascend Collection Hotel
Chincoteague Inn

Chincoteague Inn

2 out of 5
4417 Deep Hole Road, Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is ₩119,620 per night from Nov 2 to Nov 3
₩119,620
₩134,330 total
Nov 2 - Nov 3
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"I stayed at their property years ago when I first came to visit and decided to stay there again they did a remodel and I loved the update to the hotel. Everything was clean and quiet. Hopefully when I come back next time, I can stay there again."

Reviewed on Oct 4, 2025

Chincoteague Inn
See all 751 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.