Book Hotels in Crumpton, MD
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Top Crumpton hotels

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

Holiday Inn Express & Suites Middletown by IHG
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

Fairfield Inn & Suites by Marriott Middletown
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

Hampton Inn Middletown
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

Comfort Inn & Suites Chestertown
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

Inn at Haven Harbour
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

The Lodge at Great Oak Landing
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

Quality Inn
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

Red Roof Inn & Suites Chestertown
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
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
Recent Crumpton hotel reviews by fellow wanderers

Comfort Inn & Suites Chestertown
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Nice hotel"
A verified traveler stayed at Comfort Inn & Suites Chestertown
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