Deep Hole Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Packages with flights are ATOL protected

Your Deep Hole Holiday

Take the stress out of organising your next exciting adventure with a Deep Hole holiday 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 holiday to Deep Hole today.

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

Top hotels in Deep Hole

Sunrise Shore - Waterfront; Private pool & hot tub!

Sunrise Shore - Waterfront; Private pool & hot tub!

Chincoteague Island VA
9/10 Wonderful! (15 reviews)
We Loved Staying at Sunrise Shore ! The view from inside the Home is so much better then the pictures !! Our Family/Grandchildren had a Wonderful time in the Pool and the Jacuzzi is very much a Great Perk !

Reviewed on 17 Jul 2025

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Sunrise Shore - Waterfront; Private pool & hot tub!
The Blue Crab - Your Dream Vacation awaits you!

The Blue Crab - Your Dream Vacation awaits you!

2 out of 5
Chincoteague Island VA
9.8/10 Exceptional! (14 reviews)
This was the perfect house for us! We enjoyed the one floor living, the large kitchen and counter space was more than sufficient. The linens and towels were provided which was one less thing to have to pack. We enjoyed being close to town and all the restaurants, the park, and the beach. Communication ...

Reviewed on 23 Oct 2025

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The Blue Crab - Your Dream Vacation awaits you!
Blue Moon - Pet friendly; Great location!

Blue Moon - Pet friendly; Great location!

Chincoteague Island VA
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Blue Moon - Pet friendly; Great location!
See all 708 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Deep Hole travel package cost?
Our Deep Hole packages, which start at just , are an awesome way to save big bucks. Select your favourite hotels, flights and rental car to create a custom-built trip.
If I'm not able to travel, can I cancel my Deep Hole travel package?
Because we know life is full of surprises, the answer is yes. For further information, head to our Customer Service Portal. But generally speaking, if you've booked your Deep Hole travel package in the last 24 hours, you may be able to change or cancel it for free. Your hotel, airline or car rental company may impose a fee if your booking is older than that.
How do I get a cheap travel package to Deep Hole?
Search for flights that fit your schedule, add a hotel room to your booking and watch the savings rack up with a Deep Hole holiday package. It's as easy as that! From hotels and flights to activities and rental cars, Expedia makes travelling on the cheap easy. And with more than 550 air carriers and 1,000,000 properties across the globe to pick from, you'll never be short of choice.
Does Expedia offer Book Now, Pay Later Deep Hole holidays?
Expedia has teamed up with online lender Klarna to make your next trip a bit easier on the wallet. Paying by instalment means you can spread the costs of your next adventure, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that works with your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that suit all types of budgets, so you can take that well-earned holiday sooner.
  • Pay in instalments holidays: If you'd like to pay off your escape across multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you stumble on an awesome deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock it in.

Where should I stay in Deep Hole?
With so much to do in Deep Hole, it'd be handy for you to book a hotel close to its attractions. Museum of Chincoteague, Oyster Bay and Robert N. Reed Downtown Waterfront Park are some fascinating ones to add to your to-do list.
What are the top hotels in Deep Hole?
If it's your first time staying in Deep Hole, secure a room at Comfort Suites Chincoteague Island Bayfront Resort or Chincoteague Inn. Both hotels offer comfy beds and are favourites with many travellers.
How far in advance should I book my Deep Hole holiday?
Reward yourself with the widest variety and the cheapest prices by booking your Deep Hole holiday early. Air carriers tend to publish flights anywhere up to 12 months prior to departure, so start locking things in as soon as possible. That said, Expedia is committed to giving you the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Deep Hole travel package include?
It comes down to what kind of escape you have in mind. Deep Hole travel deals can include flights, car rentals and hotels. You can mix and match to find the package that fits your needs. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Deep Hole travel package?
Design deals to suit your budget with an Expedia package. Hotels, flights, rental cars — we're a one-stop shop for all of them. You'll save loads just by combining your bookings. Whether you're embarking on a winter snow adventure or sunning yourself on a warm beach, your perfect holiday is just clicks away.
Can I choose my airline with a Deep Hole Expedia travel package?
Yes, definitely. Expedia has more than 550 airline partners to select from all over the world. With such a big range of choice, finding the perfect carrier to fly you to Deep Hole will be a breeze.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.