Crumpton Holidays

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Your Crumpton Holiday

Our Crumpton holiday packages provide countless opportunities to enjoy new sights, sounds and sensations. And with all the details taken care of, you can let go and enjoy your city escape without a worry in the world. Want to tour the sights but don't know where to begin? Every trip to Crumpton should include Tilmons Island Winery. No matter your travel plans or budget, putting together a tailored Crumpton holiday is a cinch with Expedia.

Crumpton Holiday

Crumpton Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
7ºC
Max Temp Summer
27ºC

Our pick of the best 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 AU$192 per night from 3 Aug to 4 Aug
AU$192
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (775 reviews)
"Smokers smoking at parking lot entry."

Reviewed on 1 Jul. 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 AU$116 per night from 13 July to 14 July
AU$116
13 July - 14 July
includes taxes & fees
7.2/10 Good! (370 reviews)
"Had a good time and enjoyed the quietness at the hotel."

Reviewed on 3 Jul. 2025

Red Roof Inn & Suites Chestertown
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown
2.5 out of 5
411 MERRIMAC AVENUE, Middletown, DE
The price is AU$225 per night from 27 July to 28 July
AU$225
27 July - 28 July
includes taxes & fees
9.2/10 Wonderful! (247 reviews)
"Nice place to stay"

Reviewed on 30 Jun. 2025

Fairfield Inn & Suites by Marriott Middletown
See all 180 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Crumpton holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. However, how much your holiday 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 holiday packages. Opting to travel in quieter months means you'll typically find lower prices on accommodation and flights.
How many days is enough for Crumpton?
The ideal duration for your Crumpton holiday 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 holiday package as early as possible.
Is it cheaper to book a Crumpton holiday as a package?
An Expedia holiday 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 holiday 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 favourite time of year and the activities available will also help you decide when to holiday 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 holiday 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.