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.
"We had a wonderful long weekend at the cottage. It is beautifully decorated and very clean. It was perfect for our needs. We spent our days boating on the upper bay (gorgeous weather) and evenings relaxing on the deck with a perfect view of the sunset and turkey point lighthouse. Thank you Chris ..."

Reviewed on Sep 1, 2026

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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
$95 nightly
The price is $105 total per night from Nov 8 to Nov 9
$105 total
Nov 8 - Nov 9
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. ...
"The room was clean, but the lotion and body wash dispensers were not refilled prior to us checking in. The body wash dispenser was empty and I didn't know it prior to getting into the shower. We used the last kleenex tissue out of the box around 10 pm an called the front desk. Someone picked up but ..."

Reviewed on Oct 10, 2026

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

Hampton Inn Middletown

2.5 out of 5
117 Sandhill Dr Middletown DE
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $115 total per night from Nov 8 to Nov 9
$115 total
Nov 8 - Nov 9
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 ...
"The male employee working night shift hours on 10/03/2026 was more than accommodating and polite."

Reviewed on Oct 4, 2026

Opens in a new windowHampton Inn Middletown
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 Oct 18 to Oct 19
$80 total
Oct 18 - Oct 19
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 ...
Opens in a new windowRed Roof Inn & Suites Chestertown
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
$101 nightly
The price is $112 total per night from Oct 25 to Oct 26
$112 total
Oct 25 - Oct 26
Total with taxes and fees
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 ...
Opens in a new windowFairfield Inn & Suites by Marriott Middletown
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 Nov 9 to Nov 10
$93 total
Nov 9 - Nov 10
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 ...
Opens in a new windowQuality Inn Smyrna
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
$124 nightly
The price is $137 total per night from Oct 14 to Oct 15
$137 total
Oct 14 - Oct 15
Total with taxes and fees
A golf course, 2 restaurants, and a 24-hour gym are all featured at this smoke-free lodge. Dine at the beachfront restaurant and relax with sun loungers. Relax ...
Opens in a new windowThe Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
$98 nightly
The price is $109 total per night from Nov 8 to Nov 9
$109 total
Nov 8 - Nov 9
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 ...
Opens in a new windowComfort Inn & Suites Chestertown
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall MD
This villa features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. ...
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Opens in a new windowStunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
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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 201 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

Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway

4 out of 5
Posted 6 days ago
Travelocity Verified Review
"The area felt safe, the front desk guy was very kind. The room wasn’t in amazing condition but wasn’t terrible"
A verified traveler stayed at Relax Inn Smyrna Dover Coastal Gateway
Relax Inn Smyrna Dover Coastal Gateway

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