Book Hotels in Crumpton, MD

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Top Crumpton hotels

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
This cottage features a garden, laundry facilities, and barbecue grills.
"Clean and nicely decorated"

Reviewed on Sep 21, 2025

Opens in a new windowWaterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

2.5 out of 5
315 Auto Park Dr, Middletown, DE
Fully refundable
$116 nightly
The price is $129 total per night from Oct 5 to Oct 6
$129 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. ...
"Clean room, We checked in with Andrea Friend ans i must say she was a pleasure ! Very informative, Andrea spelled out all details to me very clearly with Beautiful smile. No shopping was don't. Air conditioning was great. It was a wonderful clean safe experience for our one night stay. Thank You ..."

Reviewed on Sep 28, 2025

Opens in a new windowHoliday Inn Express & Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 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 Oct 19 to Oct 20
$115 total
Oct 19 - Oct 20
Total with taxes and fees
An indoor pool is featured at this hotel, along with free WiFi in public areas and a safe deposit box. Enjoy the free continental breakfast each morning. Staff ...
"Shops were nearby. Delicious breakfast 😋. Excellent customer services."

Reviewed on Sep 28, 2025

Opens in a new windowFairfield 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
$121 nightly
The price is $134 total per night from Oct 30 to Oct 31
$134 total
Oct 30 - Oct 31
Total with taxes and fees
This hotel features 20 restaurants, an indoor pool, and a hot tub. Enjoy a meal in one of the 3 coffee shops/cafes and perks like free buffet breakfast and free ...
"Clean room"

Reviewed on Sep 23, 2025

Opens in a new windowHampton Inn Middletown
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
$117 nightly
The price is $130 total per night from Oct 30 to Oct 31
$130 total
Oct 30 - Oct 31
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...
"Nice hotel"

Reviewed on Sep 29, 2025

Opens in a new windowComfort Inn & Suites Chestertown
Inn at Haven Harbour

Inn at Haven Harbour

3 out of 5
20950 Rock Hall Ave, Rock Hall, MD
Fully refundableReserve now, pay when you stay
$213 nightly
The price is $237 total per night from Oct 2 to Oct 3
$237 total
Oct 2 - Oct 3
Total with taxes and fees
This bed & breakfast features 2 restaurants and a seasonal outdoor pool. Relax with a drink at the beach bar and enjoy free perks like continental breakfast ...
"Friendly staff at check in. This lady was helpful thru entire stay. Her name is Sharon. The Harbor had a Luau on Saturday which we attended since our son is a slip holder. Great weekend."

Reviewed on Sep 26, 2025

Opens in a new windowInn at Haven Harbour
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
$147 nightly
The price is $163 total per night from Oct 2 to Oct 3
$163 total
Oct 2 - Oct 3
Total with taxes and fees
A golf course, a 24-hour gym, and a restaurant are all featured at this smoke-free lodge. Relax with a drink at one of the 3 bars/lounges and enjoy free perks ...
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"

Reviewed on Sep 5, 2025

Opens in a new windowThe Lodge at Great Oak Landing
Quality Inn

Quality Inn

2.5 out of 5
190 Stadium St, Gateway North Plaza, Smyrna, DE
$87 nightly
The price is $97 total per night from Oct 30 to Oct 31
$97 total
Oct 30 - Oct 31
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
"Good property"

Reviewed on Sep 4, 2025

Opens in a new windowQuality Inn
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
$81 nightly
The price is $90 total per night from Oct 8 to Oct 9
$90 total
Oct 8 - Oct 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A lobby fireplace, laundry facilities, and free newspapers are also on ...
"Room temperature was good. Room was also very spacious and clean."

Reviewed on Sep 27, 2025

Opens in a new windowRed Roof Inn & Suites Chestertown
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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

What are the top kid-friendly hotels in Crumpton?
From thoughtful amenities to larger rooms, kid-friendly hotels are equipped with features that can help transform a good family vacation into an amazing one. These Crumpton properties make getting away with little ones a piece of cake: You'll be well looked after at Pine Forest Farm - A Farm Fit for a Princess!. It comes with a playground, animal viewing activities and a passion for making families feel at home. Charming Chestertown Waterfront Cottage is another top pick. After a long day of exploring, come home to your comfortable room and perks like a playground and animal viewing activities.
Where can I find cheap hotels in Crumpton?
At Travelocity you'll find really nice hotels in Crumpton at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Crumpton rather than in Crumpton. We may find you even better rates, too.
How do I find the best Crumpton hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Crumpton then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Crumpton?
The cheapest hotel in Crumpton is $90. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Crumpton?
There are 178 hotels in Crumpton on Travelocity.
What are the best hotels in Crumpton?
Crumpton has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Crumpton for you!
When is the best time to visit Crumpton?
If you want the joy of a fun-filled trip in peak season, visit Crumpton during March, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as January, October and December.
When is the cheapest time to stay in Crumpton?
Based on historic data is usually the cheapest month to visit Crumpton. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Crumpton?
There are multiple hotels in Crumpton that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Crumpton. We have plenty of kid-friendly hotels in Crumpton to choose from on Travelocity!
Why book a hotel in Crumpton through Travelocity?
Because we have the top hotels in Crumpton! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Crumpton on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

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