Crumpton Vacations from $446

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Your Crumpton Vacation

Enjoy unforgettable adventures when you book a Crumpton vacation package. Whether you're a foodie, history buff or just a traveler who loves to discover new places, there's something for everyone in this vibrant city. Crow Farm and Vineyard and Tilmons Island Winery are among the must-see sights to check out during a trip to Crumpton. No matter your travel plans or budget, organizing your ultimate tailored Crumpton vacation is a cinch with Expedia.

The Latest Crumpton vacation packages

Price found within the past 48 hours. Click for updated prices.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
Price was $696, price is now $446 per person
$446
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,868 reviews)
Great location for walking to downtown Annapolis. Room was very nice.

Reviewed on Apr 2, 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
Price was $1,088, price is now $593 per person
$593
per person
Jun 14 - Jun 17
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,065 reviews)
Best place to stay in dc. On the river where the nightlife is, but not far away from all the touristy/iconic spots. It was just logistically perfect. The room was nice, big, and clean. The concierge couldn’t be better. The desk staff was a hit or miss though. They were either the best ever or the worst. It was apparent the bad ones missed the training bc it is obvious this hotel wants to stand out for its great hospitality. I just wanted a coffee cup. Never got one.

Reviewed on Apr 1, 2026

Hotel AKA Washington Circle

Hotel AKA Washington Circle

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $818, price is now $517 per person
$517
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,244 reviews)
Great hotel, perfect location the staff were very helpful and breakfast was delicious

Reviewed on Apr 3, 2026

The Westin DC Downtown

The Westin DC Downtown

4 out of 5
Downtown Washington D.C.
Price was $951, price is now $629 per person
$629
per person
Jun 5 - Jun 8
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,005 reviews)
Clean room. Helpful staff but long lines. Hard to use amenities in mandatory fee.

Reviewed on Apr 1, 2026

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
Save 100% on your flight
Price was $656, price is now $446 per person
$446
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,340 reviews)
Extremely well kept facility. Great location. Easy walk to the Capital One Arena.

Reviewed on Apr 3, 2026

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Crumpton Hotel Deals

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

3 out of 5
411 MERRIMAC AVENUE Middletown DE
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $115 total per night from May 3 to May 4
$115 total
May 3 - May 4
Total with taxes and fees
9.2/10 Wonderful! (364 reviews)
Pool seemed over chlorinated. Had to go out and buy goggles

Reviewed on Mar 21, 2026

Fairfield Inn & Suites by Marriott Middletown
Hampton Inn Middletown

Hampton Inn Middletown

2.5 out of 5
117 Sandhill Dr Middletown DE
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from May 3 to May 4
$109 total
May 3 - May 4
Total with taxes and fees
8.8/10 Excellent! (892 reviews)
A

Reviewed on Mar 29, 2026

Hampton Inn Middletown
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
$111 nightly
The price is $123 total per night from May 3 to May 4
$123 total
May 3 - May 4
Total with taxes and fees
8.6/10 Excellent! (894 reviews)
The breakfast was as one would expect. Nothing unusual. I wish these hotels wouldn’t use so much plastic. Everything was clean. Chestertown is wonderful. Good restaurants. Much to see. The hotel is not fancy. Just a reliable place to be. Nothing unexpected. All good.

Reviewed on Apr 3, 2026

Comfort Inn & Suites Chestertown
See all 184 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.

Find the Best Crumpton Vacation Packages

Crumpton Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Crumpton vacation package cost?
You can pick up a vacation package to this popular destination from $446 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, October and December are great times to look for cheap Crumpton vacation packages. Opting to travel in less busy months means you can usually find lower prices on hotels and flights.
How many days is enough for Crumpton?
Typically, a handful of days is enough to go to the major attractions during your Crumpton vacation. But if you prefer to have some time to unwind or take day tours, consider extending your trip.
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.
Does Expedia offer Book Now, Pay Later Crumpton vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Crumpton trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.