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 MD
This cottage features a garden, laundry facilities, and barbecue grills.
The cottage is immaculate and comfortable and offers a partial view of the water from the back deck and the kitchen. A very short stroll a block down the street leads to a beautiful full view of the water, amazing sunsets, the turkey point lighthouse and soaring eagles.

Reviewed on Mar 26, 2026

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Opens in a new windowWaterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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 31 to Jun 1
$115 total
May 31 - Jun 1
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 ...
New, clean and helpful staff. Walls and floors are thin. We had to move rooms because kids were running around above us and we could hear them talking. Once we moved to the top floor (at 8:30 pm), we were fine.

Reviewed on May 15, 2026

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
$118 nightly
The price is $131 total per night from May 25 to May 26
$131 total
May 25 - May 26
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 ...
Everything was amazing

Reviewed on May 14, 2026

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
Fully refundable
$108 nightly
The price is $120 total per night from Jun 14 to Jun 15
$120 total
Jun 14 - Jun 15
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 ...
Plenty of parking, various items for breakfast, family friendly, close to many location

Reviewed on May 12, 2026

Opens in a new windowComfort Inn & Suites Chestertown
Relax Inn Smyrna

Relax Inn Smyrna

2 out of 5
1648 S Dupont Blvd Smyrna DE
$101 nightly
The price is $108 total per night from May 18 to May 19
$108 total
May 18 - May 19
Total with taxes and fees
Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free self parking.
I did not end up staying at this property. I made the reservation and, within about 10 minutes, requested a cancellation after seeing the location in person, but my request was denied. Upon arrival, I did not feel safe. The parking area appeared unsecured, and the overall environment raised concerns. ...

Reviewed on May 6, 2026

Opens in a new windowRelax Inn Smyrna
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
$84 nightly
The price is $93 total per night from May 26 to May 27
$93 total
May 26 - May 27
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 ...
It was cost effective but..... cleanliness was a major concern. Chairs in room were stained, comforter was soiled, questioned if fresh sheets were used, pillows need replacement, bathroom needed upkeep. For a non smoking room, air freshener would help. Hallways were too dark in daylight.

Reviewed on May 16, 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
$72 nightly
The price is $80 total per night from May 24 to May 25
$80 total
May 24 - May 25
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 ...
Clean lady was nice help me out

Reviewed on Apr 26, 2026

Opens in a new windowRed Roof Inn & Suites Chestertown
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
$114 nightly
The price is $127 total per night from May 31 to Jun 1
$127 total
May 31 - Jun 1
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. ...
Opens in a new windowHoliday Inn Express & Suites Middletown by IHG
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
$151 nightly
The price is $168 total per night from May 18 to May 19
$168 total
May 18 - May 19
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 ...
Opens in a new windowThe Lodge at Great Oak Landing
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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 187 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

Quality Inn Smyrna

Quality Inn Smyrna

2 out of 5
Posted 1 day ago
Travelocity Verified Review
"It was cost effective but..... cleanliness was a major concern. Chairs in room were stained, comforter was soiled, questioned if fresh sheets were used, pillows need replacement, bathroom needed upkeep. For a non smoking room, air freshener would help. Hallways were too dark in daylight."
A verified traveler stayed at Quality Inn Smyrna
Quality Inn Smyrna

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