Deep Hole Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Deep Hole Vacation Packages

Deep Hole Hotel Deals

Quaint Cottages Near Everything on Beach Road

Quaint Cottages Near Everything on Beach Road

Chincoteague
9.4/10 Exceptional! (36 reviews)
Last minute
"We booked this at the very last minute so we could clean out our father’s home (he passed the week before). It was perfect for our needs. One caution…the grass has tiny little burrs that stick to socks and flip flops. Nothing to do about them but if you have a dog, check their paws. We were even ..."

Reviewed on Sep 29, 2024

Get rates
Quaint Cottages Near Everything on Beach Road
An Unfettered View - Beautiful ranch w/ boat dock!

An Unfettered View - Beautiful ranch w/ boat dock!

Chincoteague Island
Fun without sun.
"Even with the wind and rain we had a great time."

Reviewed on Jun 27, 2023

Get rates
An Unfettered View - Beautiful ranch w/ boat dock!
Oyster Bay Hideaway on Chincoteague Island!

Oyster Bay Hideaway on Chincoteague Island!

Chincoteague Island
10/10 Exceptional! (9 reviews)
Really nice back view
"I stayed for Pony Swim. It was beautiful overlooking marsh and very convenient"

Reviewed on Aug 5, 2025

Get rates
Oyster Bay Hideaway on Chincoteague Island!
See all 742 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.

Frequently asked questions

How much does a Deep Hole vacation package cost?
You can snap up a vacation package to this destination 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?
The off-season is the best time to visit Deep Hole if you're trying to keep costs down. Another tip for finding cheap Deep Hole vacation packages? Try to avoid public holidays and any major events.
How many days is enough for Deep Hole?
Typically, a handful of days is enough to tick off the major attractions during your Deep Hole vacation. However, if you prefer to have time to chill out or take day trips, think about extending your trip.
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. Choose when to get away: Check your schedule and pack your bags. Your preferred season and the activities on offer will also help you decide when to vacation in Deep Hole.
  2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to airfares and activities. Your accommodations will probably be the biggest expense during your trip to Deep Hole.
  3. Work out your trip length: Think about how long you'd like to spend exploring Deep Hole. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your airfare and accommodations: Once you've settled on your dates and duration, lock in the perfect Deep Hole vacation package for you.

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