Deep Hole Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Your Deep Hole Vacation

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

Top Holiday Package Deals in Deep Hole

Price found within the past 48 hours. Click for updated prices.
Sunrise Inn By OYO Newport News US-60

Sunrise Inn By OYO Newport News US-60

2.5 out of 5
North Newport News
Price was CA $1,243, price is now CA $1,080 per person
CA $1,080
per person
Sep 5 - Sep 12
just found
Roundtrip non-stop flight included
Montreal (YMQ) to Norfolk (ORF)
5/10 (237 reviews)

The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Northeast Virginia Beach
Price was CA $1,611, price is now CA $1,344 per person
CA $1,344
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Norfolk (ORF)
8/10 Very good! (1,007 reviews)
Ok

Reviewed on Aug 5, 2026

Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
Central Newport News
Price was CA $1,432, price is now CA $1,238 per person
CA $1,238
per person
Sep 5 - Sep 12
just found
Roundtrip non-stop flight included
Montreal (YMQ) to Norfolk (ORF)
8.8/10 Excellent! (1,071 reviews)
Front sleeks kept saying they didn’t work there normally and weren’t helpful.

Reviewed on Aug 4, 2026

Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was CA $1,416, price is now CA $1,244 per person
CA $1,244
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Norfolk (ORF)
8.8/10 Excellent! (1,007 reviews)

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News

2 out of 5
Downtown Newport News
Price was CA $2,093, price is now CA $1,844 per person
CA $1,844
per person
Sep 5 - Sep 12
just found
Roundtrip non-stop flight included
Montreal (YMQ) to Norfolk (ORF)
7.4/10 Good! (3 reviews)
"Terrible experience—don't waste your time or money. They double-booked and canceled my reservation without informing me until the day of my arrival. They refused to issue a full refund, and there was a complete lack of communication. No one took accountability, and now, five days later, I'm still trying to obtain the remainder of my refund. Ridiculous!"

Reviewed on Mar 25, 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

Deep Hole Hotel Deals

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 Sep 30, 2025

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Oyster Catcher | Deep Creek Waterfront w/ Deep Water Dock, Screened Porch, Guest Cottage & Pets
Sunrise Shore | Waterfront Oyster Bay Home w/ Pool, Hot Tub, Panoramic Views & Modern Luxury

Sunrise Shore | Waterfront Oyster Bay Home w/ Pool, Hot Tub, Panoramic Views & Modern Luxury

Chincoteague Island VA
8.6/10 Excellent! (37 reviews)
"This was our final stay. The furniture is gross, the beds are broken, one had bugs that my teen grandaughter had more bites all over her body each morning! The drains are clogged all the time.Kitchen had Rat Poison in the FOOD Pantry!Kitchen drain was clogged all the time & made it difficult to even ..."

Reviewed on Jul 16, 2026

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Sunrise Shore | Waterfront Oyster Bay Home w/ Pool, Hot Tub, Panoramic Views & Modern Luxury
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! (6 reviews)
"Cozy and hidden away from the main road. Plenty of room for dogs to roam around."

Reviewed on Jul 13, 2026

Get rates
Escape at Deep Hole Hideaway | Chic 2BR Retreat w/ Full Kitchen, Daybed + Sleeper Sofa, Pet Friendly
See all 739 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Deep Hole vacation package cost?
You'll find cheap prices from CA $1,080 on Expedia for your Deep Hole getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Deep Hole costs.
What are the cheapest months to go to Deep Hole?
Travel in the off-peak season and you're likely to score cheap Deep Hole vacation packages. Remember that public holidays and major events and festivals can have an impact on prices, so do a little research before booking.
How many days is enough for Deep Hole?
Usually, a handful of days is enough to check out the main sights during your Deep Hole vacation. But if you'd like to have some time to rest or take day tours, think about extending your itinerary.
How to find the best Deep Hole package deals?
Bagging a cheap Deep Hole package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Deep Hole package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Deep Hole vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Deep Hole vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Deep Hole?
Enjoy amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Deep Hole trip.
How to plan a trip to Deep Hole?

  1. Choose when to get away: Check your diary and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to visit Deep Hole.
  2. Set your budget: Factor in costs such as transportation, flights and meals when working out how much to save for your trip to Deep Hole. Then, select a hotel that matches your budget, whether that's an affordable option or a lavish getaway.
  3. Set the duration of your trip: Start by listing all the activities and attractions you want to experience in Deep Hole. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Deep Hole vacation package that brings all your bookings together.

Things to do

Small Group Boat Tours of Chincoteague & Assateague - Wild Ponies

Boat Tours of Chincoteague & Assateague - Wild Ponies

CA $111
per adult
Boat Tours of Chincoteague & Assateague - Wild Ponies
Small-Group Sunset Boat Tour around Chincoteague & Assateague Islands

Chincoteague & Assateague Small-Group Sunset Boat Tour

CA $126
per adult
Chincoteague & Assateague Small-Group Sunset Boat Tour
Chincoteague Dolphin Watching Boat Tour

Chincoteague's Dolphin Watching Boat Tour

CA $125
per adult
Chincoteague's Dolphin Watching Boat Tour
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.