Deep Hole Holidays from £1,073

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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.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was £1,410, price is now £1,073 per person
£1,073
per person
27 Aug - 2 Sept
found 1 day ago
Return direct flight included
London (LGW) to Salisbury (SBY)
9.4/10 Exceptional! (784 reviews)
Room was cleaned daily; all staff with whom we interacted were pleasant and helpful. Must be well-managed.

Reviewed on 16 Jul 2026

The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Northeast Virginia Beach
Price was £1,790, price is now £1,401 per person
£1,401
per person
27 Aug - 2 Sept
found 1 day ago
Return flight included
London (LGW) to Norfolk (ORF)
9.4/10 Exceptional! (27 reviews)
While there, the heat index was over 100 and the ac unit could not keep up. Our room was over 80 the first day/night there. They did supply a portable ac unit to help. After that the stay was better. It’s clean and great location. Great price for what we got. The living space was very open and nice. Perfect for what we needed.

Reviewed on 15 Jul 2026

The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
Price was £1,501, price is now £1,175 per person
£1,175
per person
27 Aug - 2 Sept
found 1 day ago
Return flight included
London (LGW) to Norfolk (ORF)
8.2/10 Very good! (1,549 reviews)
Staff was professional, courteous, informative,making us feel welcome, especially "Queeny" and the "Gentleman" at the front desk. Unfortunately I don't know his name but he extremely courteous as Resort was clean well kept,all in all,very comfortable and well organized. KUDOS ATRIUM RESORT!!! 10 + 10 IS MY RATING

Reviewed on 15 Jul 2026

The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
Price was £1,484, price is now £1,170 per person
£1,170
per person
27 Aug - 2 Sept
found 1 day ago
Return flight included
London (LGW) to Norfolk (ORF)
7.6/10 Good! (1,562 reviews)
Was an hour late getting our room but certainly not offered an hour late to check out.

Reviewed on 13 Jul 2026

The Capes Hotel

The Capes Hotel

3 out of 5
Northeast Virginia Beach
Price was £1,755, price is now £1,399 per person
£1,399
per person
27 Aug - 2 Sept
found 1 day ago
Return flight included
London (LGW) to Norfolk (ORF)
8.6/10 Excellent! (494 reviews)
Great location Staff was very helpful Lori was next level helpful We’d stay here again

Reviewed on 8 Jul 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
A field of horses near a body of water with a crowd in the background.

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.

Find hotels in Downtown Chincoteague

Top hotels in Deep Hole

Oyster Catcher | Deep Creek Waterfront w/ Deep Water Dock, Screened Porch, Guest Cottage & Pets

Oyster Catcher | Deep Creek Waterfront w/ Deep Water Dock, Screened Porch, Guest Cottage & Pets

Chincoteague Island VA
10/10 Exceptional! (4 reviews)
"Sunrise views from the porch were breathtaking."

Reviewed on 30 Sept 2025

Get rates
Oyster Catcher | Deep Creek Waterfront w/ Deep Water Dock, Screened Porch, Guest Cottage & Pets
Escape at Deep Hole Hideaway | Chic 2BR Retreat w/ Full Kitchen, Daybed + Sleeper Sofa, Pet Friendly

Escape at Deep Hole Hideaway | Chic 2BR Retreat w/ Full Kitchen, Daybed + Sleeper Sofa, Pet Friendly

Chincoteague Island VA
9/10 Wonderful! (4 reviews)
"The rental unit description did not communicate that this property had another rental unit above it. This was particularly disappointing based on the property description as a "retreat"."

Reviewed on 1 Jul 2026

Get rates
Escape at Deep Hole Hideaway | Chic 2BR Retreat w/ Full Kitchen, Daybed + Sleeper Sofa, Pet Friendly
Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague

Chincoteague VA
The price is £280 per night from 3 Aug to 4 Aug
£280
3 Aug - 4 Aug
includes taxes & fees
10/10 Exceptional! (3 reviews)
"Very nice and well designed property. As soon as you open the door, you can tell that a lot of love and dedication came into designing this beautiful little cottage.Done with taste. Well located, away from the busy beach town center, yet very close to the main street (Maddox Street) and to the National ..."

Reviewed on 13 Jul 2026

Cozy 2-bedroom house in Chincoteague
See all 741 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 £1,073, 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

Small Group Boat Tours of Chincoteague & Assateague - Wild Ponies

Boat Tours of Chincoteague & Assateague - Wild Ponies

£59
per adult
Boat Tours of Chincoteague & Assateague - Wild Ponies
Guided Kayak Tour to see ponies, birds, dolphins and more

Guided Kayak Tour to see ponies, birds, dolphins and more

£57
per adult
100% of travellers recommend
Guided Kayak Tour to see ponies, birds, dolphins and more
Guided Jet Ski Rentals in Chincoteague Island, VA

1-Hour Guided Jet Ski Rental & Eco Tour in Chincoteague Island

£94
per adult
1-Hour Guided Jet Ski Rental & Eco Tour in Chincoteague Island
See all activities in Chincoteague

* 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.