Deep Hole Vacations from $411

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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.

The Latest Deep Hole vacation packages

Price found within the past 48 hours. Click for updated prices.
Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $654, price is now $411 per person
$411
per person
Nov 8 - Nov 15
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,695 reviews)
The shopping was good. You can walk to most everything you want or take the trolley. The view was awesome. My room however could use some updates and maintenance

Reviewed on Sep 27, 2025

Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Price was $2,947, price is now $1,536 per person
$1,536
per person
Nov 8 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
No reviews
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $657, price is now $413 per person
$413
per person
Nov 8 - Nov 15
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,017 reviews)
It was a cool spot. Just gotta tighten up on the grounds upkeep.

Reviewed on Sep 27, 2025

The Sanderling

The Sanderling

4 out of 5
Save 100% on your flight
Price was $1,139, price is now $767 per person
$767
per person
Nov 8 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (512 reviews)
Staff was excellent!! 1st room not good. Needed maintenance and upkeep. Fan needed dusting. After dinner found ants in bed. Staff moved us to a different room which was better maintained but unfortunately it didn’t have the ocean view. Beach was beautiful loved the chairs and umbrellas provided. Neat fire pits area. For the costs per night I expect better rooms. Staff surprised me with bottle of champagne and a heartfelt note for my special birthday. It was a nice surprise.

Reviewed on Sep 28, 2025

Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

4 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $609, price is now $421 per person
$421
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
8.4/10 Very Good! (1,014 reviews)
We enjoyed our stay, however we would have enjoyed it more if we could have sit on the balcony once we were in for the night. Our partial ocean view room was on the 29th street side (opposite side of the Neptune statue) and was above two huge hvac fans that were so loud we could not sit on the balcony. We were on the twelfth floor. We asked for a different room but there were none available. Just be sure you do not get a partial ocean view on that side. We would go back. The restaurant and open bar area is wonderful and the staff were very friendly. They even had rocking chairs to sit out and enjoy the ocean at night. This is a great location as well.

Reviewed on Sep 26, 2025

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Deep Hole Hotel Deals

Quaint Cottages Near Everything on Beach Road

Quaint Cottages Near Everything on Beach Road

Chincoteague
9.4/10 Exceptional! (38 reviews)
"This was a charming little place! Our host was very communicative and the check-in and check-out processes were easy. It was clean and tidy and perfect for a weekend stay."

Reviewed on Aug 17, 2025

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Quaint Cottages Near Everything on Beach Road
Sunrise Shore - Waterfront; Private pool & hot tub!

Sunrise Shore - Waterfront; Private pool & hot tub!

Chincoteague Island
9/10 Wonderful! (15 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; Private pool & hot tub!
The Blue Crab - Your Dream Vacation awaits you!

The Blue Crab - Your Dream Vacation awaits you!

2 out of 5
Chincoteague Island
9.6/10 Exceptional! (12 reviews)
"The Blue Crab was perfect for our family vacation. It was beautiful, clean, spacious, and had everything we needed to enjoy our stay. If we come back, we’ll be staying at The Blue Crab again!"

Reviewed on Jul 22, 2025

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The Blue Crab - Your Dream Vacation awaits you!
See all 751 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.

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Frequently asked questions

How much does a Deep Hole vacation package cost?
You can snap up a vacation package to this destination from $411 on Expedia. But how much your vacation to Deep Hole costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Deep Hole?
October, November and December are the best times to look for cheap Deep Hole vacation packages. Traveling in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Deep Hole?
With a well-organized schedule, you can easily tick off the most popular Deep Hole attractions in a handful of days. But if you'd like to discover lesser-known spots or go on day trips, consider booking your Deep Hole vacation for longer.
How to find the best Deep Hole package deals?
Use Expedia's filter tool to find some of the best Deep Hole package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Deep Hole package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Deep Hole vacation as a package?
You can enjoy significant savings on your next Deep Hole retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Deep Hole?
If you're planning a spur-of-the-moment Deep Hole trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Deep Hole?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Deep Hole.
  2. Plan your budget wisely: In addition to the cost of your hotel, you'll need to factor in other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that could crop up during your trip to Deep Hole.
  3. Organize your Deep Hole escape with our trip planning tool: Look for and book hotels and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Deep Hole together.
  4. Decide how long to go for: Now that you're up to speed on Deep Hole, you can work out the perfect length of your break. Put together a draft plan and give yourself enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalized Deep Hole vacation package.
  6. Add on experiences and excursions: Have a look at our dedicated travel guide to find some incredible things to do in Deep Hole in Deep Hole. Book tickets or make reservations before you go to save time and avoid the stress of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Deep Hole vacation packages?
Your Deep Hole break should be an escape from your daily routine, not a source of money worries. So to allow you extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.