Deep Hole Holidays from £1,044

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    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.

Top Deep Hole Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 out of 5
per person
7 Oct - 14 Oct
found 11 hours ago
Return direct flight included
London (LON) to Salisbury (SBY)
9.2/10 Wonderful! (878 reviews)
Great stay beautiful view

Reviewed on 28 Jul 2025

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
per person
7 Oct - 14 Oct
found 11 hours ago
Return direct flight included
London (LON) to Salisbury (SBY)
9.4/10 Exceptional! (600 reviews)
Beautiful view and next to the Crab Deck All in all it was a good stay…expensive You check in at 4 and need to check out by 11 for $200+ a night. The bed was not comfortable I would think they would include the breakfast. $11 per person for a continental breakfast was disappointing esp since there is nothing nearby There is free coffee, tea or hot chocolate

Reviewed on 30 Jul 2025

Deep Hole Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Salisbury - Ocean City Wicomico Regional Airport (SBY)
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
Maui Jacks Waterpark, Robert N. Reed Downtown Waterfront Park and Captain Timothy Hill House

Top hotels in Deep Hole

Quaint Cottages Near Everything on Beach Road

Quaint Cottages Near Everything on Beach Road

Chincoteague, VA
Last minute
"We booked this at the very last minute so we could clean out our father’s home (he passed the week before). It was perfect for our needs. One caution…the grass has tiny little burrs that stick to socks and flip flops. Nothing to do about them but if you have a dog, check their paws. We were even ..."

Reviewed on 29 Sep 2024

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Quaint Cottages Near Everything on Beach Road
An Unfettered View - Beautiful ranch w/ boat dock!

An Unfettered View - Beautiful ranch w/ boat dock!

Chincoteague Island, Virginia
Fun without sun.
"Even with the wind and rain we had a great time."

Reviewed on 27 Jun 2023

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An Unfettered View - Beautiful ranch w/ boat dock!
Oyster Bay Hideaway on Chincoteague Island!

Oyster Bay Hideaway on Chincoteague Island!

Chincoteague Island, VA
10/10 Exceptional! (9 reviews)
Really nice back view
"I stayed for Pony Swim. It was beautiful overlooking marsh and very convenient"

Reviewed on 5 Aug 2025

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Oyster Bay Hideaway on Chincoteague Island!
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.
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 £1,044, 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.