Book Hotels in Crumpton, MD

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Top Crumpton hotels

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

Rock Hall MD
A gym is featured at this vacation home, along with laundry facilities and barbecue grills.
"Great location right on the triathlon route. Super charming town that was fun to bike with kids. Hosts left a great PDF with lots of suggestions for fun activities,"

Reviewed on May 31, 2026

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Opens in a new windowWelcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
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
The price is $132 total per night from Jul 5 to Jul 6
$132 total
per night
Jul 5 - Jul 6
This hotel features an indoor pool and a gym. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A safe deposit box is provided ...
"I only stayed one night, but the staff was very friendly. The facilities were amazing, and the room looked great and smelled great. When I'm in that area, I definitely will stay at this location again."

Reviewed on Jun 21, 2026

Opens in a new windowFairfield Inn & Suites by Marriott Middletown
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
The price is $117 total per night from Jul 12 to Jul 13
$117 total
per night
Jul 12 - Jul 13
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. ...
"Definitely not with the money. Garbage overspilling in front, breakfast food was disgusting, they cancelled my families room without notice. Don’t stay here"

Reviewed on Jun 28, 2026

Opens in a new windowHoliday Inn Express & Suites Middletown by IHG
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
The price is $115 total per night from Jul 26 to Jul 27
$115 total
per night
Jul 26 - Jul 27
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 ...
"Problems with checking in and washing machine not working. Staff didn’t care."

Reviewed on Jun 29, 2026

Opens in a new windowComfort Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3 out of 5
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is $168 total per night from Jul 6 to Jul 7
$168 total
per night
Jul 6 - Jul 7
A golf course and a 24-hour gym are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A picnic ...
"Is a beautiful and quiet place to relax"

Reviewed on Jun 29, 2026

Opens in a new windowThe Lodge at Great Oak Landing
Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway

2 out of 5
1648 S Dupont Blvd Smyrna DE
The price is $101 total per night from Jul 5 to Jul 6
$101 total
per night
Jul 5 - Jul 6
Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free self parking.
"House was very nice. Nice quiet place to stay. Clean room comfortable bed. I recommend it for others to stay at."

Reviewed on Jun 21, 2026

Opens in a new windowRelax Inn Smyrna Dover Coastal Gateway
Quality Inn Smyrna

Quality Inn Smyrna

2.5 out of 5
190 Stadium St, Gateway North Plaza Smyrna DE
Fully refundableReserve now, pay when you stay
The price is $94 total per night from Aug 2 to Aug 3
$94 total
per night
Aug 2 - Aug 3
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 for price paid and area"

Reviewed on Jun 29, 2026

Opens in a new windowQuality Inn Smyrna
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 $80 total per night from Jul 9 to Jul 10
$80 total
per night
Jul 9 - Jul 10
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 ...
"The property is a little older and could benefit from a good deep cleaning of carpets and upholstery, but the bed and bathroom were clean and the staff were great. Considering the price of other accomodations in the area it's an excellent value for the money if you're just looking for a clean place ..."

Reviewed on Jun 22, 2026

Opens in a new windowRed Roof Inn & Suites Chestertown
Hampton Inn Middletown

Hampton Inn Middletown

2.5 out of 5
117 Sandhill Dr Middletown DE
Fully refundableReserve now, pay when you stay
The price is $144 total per night from Jul 26 to Jul 27
$144 total
per night
Jul 26 - Jul 27
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 ...
Opens in a new windowHampton Inn Middletown
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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 $80. 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 194 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.

Recent Crumpton hotel reviews by fellow wanderers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"My husband and I stayed her for a brief get-a-way and loved it! The cottage is totally renovated and fully equipped. It has a full driveway providing excellent off street parking. Chris recommended Schaeffer’s for a dinner out in N. Chesapeake, and it was wonderful! We went to the Harmon Plantation one morning and enjoyed the lovely grounds. The house was closed that day, but we hope to come back. Thanks for a wonderful respite Chris!"
A verified traveler stayed at Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

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