Deep Hole Holidays

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    Better together

    Save up to S$134 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

Top hotels in Deep Hole

Atlantic Shores Inn and Suites

Atlantic Shores Inn and Suites

2 out of 5
6273 Maddox Blvd, Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is S$110 per night from 8 Sept to 9 Sept
S$110
8 Sept - 9 Sept
includes taxes & fees
7.2/10 Good! (1,000 reviews)
"No complaints"

Reviewed on 17 Aug, 2025

Atlantic Shores Inn and Suites
Waterside Inn

Waterside Inn

2 out of 5
3761 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,010 reviews)
"Beautiful grounds and loved the dock which went out to the bay. It is an older hotel but clean and location is good."

Reviewed on 17 Aug, 2025

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Waterside Inn
Chincoteague Inn

Chincoteague Inn

2 out of 5
4417 Deep Hole Road, Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is S$128 per night from 21 Sept to 22 Sept
S$128
21 Sept - 22 Sept
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"Location put us in walking distance to a nice seafood restaurant, and other eating places plus a good drug store."

Reviewed on 18 Aug, 2025

Chincoteague Inn
See all 744 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 holiday package cost?
You can snap up a holiday package to this destination on Expedia. But how much your holiday 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 holiday 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 holiday. 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 holiday package well in advance.
Is it cheaper to book a Deep Hole holiday as a package?
You can enjoy significant savings on your next Deep Hole retreat by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday 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 holiday 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 accommodation 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 accommodation: Once you've settled on your dates and duration, lock in the perfect Deep Hole holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.