Crumpton Vacations

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Find the Best Crumpton Vacation Packages

Crumpton Hotel Deals

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ₩156,550 per night from Aug 17 to Aug 18
₩156,550
₩173,770 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very Good! (792 reviews)
"Please move waffle station….it needs its own space! Could hardly get a plate and utensils with people trying to and waiting for their turn to make waffles. Breakfast choices just okay."

Reviewed on Aug 4, 2025

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ₩99,292 per night from Aug 21 to Aug 22
₩99,292
₩110,215 total
Aug 21 - Aug 22
includes taxes & fees
7.2/10 Good! (386 reviews)
"Great service"

Reviewed on Aug 1, 2025

Red Roof Inn & Suites Chestertown
Holiday Inn Express And Suites Middletown by IHG

Holiday Inn Express And Suites Middletown by IHG

2.5 out of 5
315 Auto Park Dr, Middletown, DE
Fully refundable
The price is ₩159,970 per night from Aug 24 to Aug 25
₩159,970
₩177,567 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (603 reviews)
"The cleanliness"

Reviewed on Aug 11, 2025

Holiday Inn Express And Suites Middletown by IHG
See all 181 properties in Crumpton
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 Crumpton vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. However, how much your vacation to Crumpton costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Crumpton?
January, February and November are great times to look for cheap Crumpton vacation packages. Opting to travel in quieter months means you'll typically find lower prices on accommodations and flights.
How many days is enough for Crumpton?
The ideal duration for your Crumpton vacation depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to hit all the major attractions and discover some hidden spots along the way.
How to find the best Crumpton package deals?
Use Expedia's handy filters to find some tempting Crumpton package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Crumpton package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Crumpton vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking hotels and flights separately. Better still, you can tailor your Crumpton trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Crumpton?
If you have your Crumpton travel dates finalized, book early to grab some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Crumpton?

  1. Choose when to go: Check your schedule and get packing. Your favorite time of year and the activities available will also help you decide when to vacation in Crumpton.
  2. Budget wisely: On top of the price of your stay, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that could arise during your trip to Crumpton.
  3. Decide your trip length: Think about how long you'd like to spend exploring Crumpton. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Crumpton 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.