Deep Hole Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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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.
The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
Price was CA $1,161, price is now CA $927 per person
CA $927
per person
May 17 - May 23
found 14 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Norfolk (ORF)
8.2/10 Very Good! (1,484 reviews)
It was a clean, super cute room close to the beach! Would boom again!

Reviewed on Mar 25, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was CA $3,679, price is now CA $2,775 per person
CA $2,775
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
9/10 Wonderful! (3,474 reviews)
Staff was pleasant, room was clean with a comfy bed, and the view was awesome.

Reviewed on Apr 12, 2026

Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was CA $1,441, price is now CA $1,114 per person
CA $1,114
per person
May 17 - May 23
found 14 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Norfolk (ORF)
8.6/10 Excellent! (1,003 reviews)
Wonderful location and very spacious for the price. Only issue was Pacific Ave was closed on Saturday night per festival and could not get back to parking lot. Very upset since no staff made us aware.

Reviewed on Apr 12, 2026

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was CA $2,776, price is now CA $2,222 per person
CA $2,222
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
8.2/10 Very Good! (704 reviews)
Please don’t believe these reviews I had an excellent experience. The hotel was older but is a mom and pop hotel family feel.

Reviewed on Mar 31, 2026

Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
Price was CA $2,217, price is now CA $1,784 per person
CA $1,784
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
7.6/10 Good! (521 reviews)
Great location, has a pool. Outdated rooms but clean and friendly staff. For the price we were happy.

Reviewed on Apr 6, 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

Downtown Chincoteague

1 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

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
8.8/10 Excellent! (34 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 Jul 17, 2025

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

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
The price is CA $257 per night from Apr 26 to Apr 27
CA $257
CA $288 total
Apr 26 - Apr 27
includes taxes & fees
9.8/10 Exceptional! (537 reviews)
The place is very relaxing Ang comfortable. I want to book the place again

Reviewed on Apr 7, 2026

Key West Cottages
See all 722 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
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Frequently asked questions

How much does a Deep Hole vacation package cost?
You'll find cheap prices from CA $927 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.