Deep Hole Holidays from £1,180
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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.
Price found within the past 48 hours. Click for updated prices.
Smithfield Station
£1,437
per person
20 Dec - 27 Dec
found 1 day ago
Return direct flight included
London (LON) to Norfolk (ORF)
9/10 Wonderful! (536 reviews)
This is my third stay and it just keeps getting better! I was in town to attend the Princess Buffet with my granddaughters which happened to be located in the hotel's restaurant. Whoever organized this event did an amazing job! The decorations, food and treats for the young princesses were wonderful and well thoughout. The best feature was the very talented young women dressed as Disney pricesses who sang and greeted each girl at their table to chat.
That being said, my room was fresh and clean as usual and my granddaughter enjoyed looking at the boats from the balcony. Check in was easy and all the staff I met was very friendly and helpful.
The Smithfield Station is very accomodating and perfectly located near all the wonderful attractions of the town of Smithfield - you wil not be disappointed!
Reviewed on 7 Oct 2026
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
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 Assateague Point.
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 Museum of Chincoteague.
Top hotels in Deep Hole
Oyster Catcher | Deep Creek Waterfront w/ Deep Water Dock, Screened Porch, Guest Cottage & Pets
Chincoteague Island VA
9/10 Wonderful! (6 reviews)
"Old and lovely house, great dock, pets allowed, kayaking access, roomy parking. We love Oyster Catcher!"
Reviewed on 5 Sept 2026
Cozy 2-bedroom house in Chincoteague
Chincoteague VA
£229
17 Oct - 18 Oct
includes taxes & fees
10/10 Exceptional! (6 reviews)
"The cottage is adorable and the owners are superb! The house was super clean, well-appointed, and in a very quiet area. I would gladly stay her again.pros:quiet well stocked kitchenwasher/dryernice tub/showercomfy bedsgreat ownerslot of thick towels and pillowscons:mosquitoes! (nothing the owner ..."
Reviewed on 7 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 Jul 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 travel package cost?
Our Deep Hole packages, which start at just £1,180, 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.
Things to do
Boat Tours of Chincoteague & Assateague - Wild Ponies
£58
per adult
Chincoteague and Assateague Island Boat Tour with Capt. John
£71
per adult
Chincoteague & Assateague Small-Group Sunset Boat Tour
£66
per adult
* 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.