Deep Hole Holidays from AU$2,119
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Your Deep Hole Holiday
When a getaway to the city is calling, answer it with a holiday package to Deep Hole. With all your travel needs in order before you leave, all you have to do here is focus on having a ball. Like to explore your new surroundings? Maui Jacks Waterpark, Robert N. Reed Downtown Waterfront Park and Oyster Bay are just three of the top-rated places to visit during a trip to Deep Hole. A couple of clicks is all it takes to craft your dream Deep Hole holiday on Expedia.
Top Holiday Package Deals in Deep Hole
Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Virginia Beach Town Center by IHG
Northwest
AU$2,119
per person
13 Oct - 20 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Norfolk (ORF)
8.4/10 Very good! (494 reviews)
The hotel and upgrades to the hotel was very nice and beautiful. Kascade entertainment area with live music was very nice.
This was my first time staying at the hotel. My room was clean and beautiful but it had a stale smell when the air conditioner went off. The fridge was on but was leaking and maintenance had to come fix it. The smell never went away.
The bathroom sliding door got stuck and took me some time to get out the bathroom because the door was stuck and maintenance came back to fix it to slide easily.
My last experience which was awful and scary was when I ordered a cold tea to drink at Kascade’s restaurant and I had a screw in the bottom of my class😞I thought it was maybe a lemon seed until I held the glass up and looked carefully and stirred my tea with my straw and I showed it to the waitress and my husband and in-lawd because we all were there to eat dinner.
The manager only said, I’m so sorry and still charged me for the tea and didn’t offer me anything which was poor management.
The hotel told me that Kascade is not part of the hotel and just rents out the space in the hotel, but it still looks bad because they are in the hotel. I did tell the desk host about my tea experience and she told me she would tell management about it.
Reviewed on 31 Aug 2026
Holiday Inn Express & Suites VA Beach Oceanfront by IHG
Northeast Virginia Beach
AU$2,338
per person
13 Oct - 20 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Norfolk (ORF)
8.8/10 Excellent! (1,012 reviews)
family friendly and close to everywhere. very relaxing and nice hotel
Reviewed on 31 Aug 2026
Our guide on 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
Downtown Chincoteague
2 out of top 10 points of interest in this area
While visiting Downtown Chincoteague, you might make a stop by sights like Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.
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.
Snotty Ridge
Snotty Ridge might not have many top sights, but Robert N. Reed Downtown Waterfront Park and Assateague Point are two attractions nearby that you can check out.
Down the Marsh
1 out of top 10 points of interest in this area
While there might not be top attractions in Down the Marsh, you can explore the larger area and discover places like Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.
Birch Town
Though Birch Town may not have many top sights, you can venture to the surrounding area to see attractions like Maui Jack's Waterpark and Assateague Lighthouse.
Our pick of the best Deep Hole Hotel Deals
Oyster Catcher | Deep Creek Waterfront w/ Deep Water Dock, Screened Porch, Guest Cottage & Pets
Chincoteague Island VA
9.2/10 Wonderful! (5 reviews)
"Pros-great location, great views from screened in back porch, loved the dock outback. The guest cottage is quite lovely.Cons-the house needs attention. Broken bed first floor, blinds in some rooms won’t go up, front door handle broken off so we never opened, holes in the screen porch, bathroom blind ..."
Reviewed on 2 Aug 2026
Sunrise Shore | Waterfront Oyster Bay Home w/ Pool, Hot Tub, Panoramic Views & Modern Luxury
Chincoteague Island VA
8.6/10 Excellent! (38 reviews)
"Over priced, neglected, on going problems that haven’t been addressed,"
Reviewed on 6 Aug 2026
Escape at Deep Hole Hideaway | Chic 2BR Retreat w/ Full Kitchen, Daybed + Sleeper Sofa, Pet Friendly
Chincoteague Island VA
9/10 Wonderful! (6 reviews)
"Cozy and hidden away from the main road. Plenty of room for dogs to roam around."
Reviewed on 13 July 2026
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 from AU$2,119 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?
- 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.
- 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.
- 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.
- Bundle your airfare and accommodation: Once you've settled on your dates and duration, lock in the perfect Deep Hole holiday package for you.
Activities
Sunset Wildlife Cruise along Assateague & Chincoteague Island
AU$94
per adult
100% of travellers recommend
Chincoteague's Up The Bay Pony and Wildlife Tour by Boat
AU$113
per adult
94% of travellers recommend
Chincoteague's and Assateague’s Grand Boat Tour with Capt.John
AU$127
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.