Book Hotels in Crumpton, MD

Start date: Check-in selected.
To Date
End date: Check-out

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Crumpton hotels

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
$260 nightly
The price is $276 total per night from Nov 19 to Nov 20
$276 total
Nov 19 - Nov 20
Total with taxes and fees
Stay at this vacation home in Rock Hall. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Ferry Park and Waterman’s Museum are located ...
The entire stay was wonderful. The Bayside Bungalow provided everything you could possibly need on vacation. The hosts were wonderful and available if you had a question or needed assistance with any detail of the stay. We will definitely be back.

Reviewed on Nov 3, 2025

Opens in a new windowBAYSIDE BUNGALOW
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 out of 5
411 MERRIMAC AVENUE Middletown DE
$108 nightly
The price is $120 total per night from Nov 23 to Nov 24
$120 total
Nov 23 - Nov 24
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 ...
Room was very clean. Staff friendly close to everything

Reviewed on Nov 12, 2025

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
$116 nightly
The price is $129 total per night from Nov 23 to Nov 24
$129 total
Nov 23 - Nov 24
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. ...
Staff was nice

Reviewed on Nov 12, 2025

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
$103 nightly
The price is $115 total per night from Dec 1 to Dec 2
$115 total
Dec 1 - Dec 2
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 ...
Absolutely YES

Reviewed on Nov 4, 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
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $113 total per night from Nov 19 to Nov 20
$113 total
Nov 19 - Nov 20
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 ...
All good

Reviewed on Nov 10, 2025

Opens in a new windowComfort Inn & Suites Chestertown
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
$113 nightly
The price is $126 total per night from Nov 18 to Nov 19
$126 total
Nov 18 - Nov 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 ...
Beautiful view

Reviewed on Nov 8, 2025

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

Relax Inn Smyrna

2 out of 5
1648 S Dupont Blvd, Smyrna, DE
$92 nightly
The price is $99 total per night from Nov 18 to Nov 19
$99 total
Nov 18 - Nov 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.
Great location

Reviewed on Nov 9, 2025

Opens in a new windowRelax Inn Smyrna
Quality Inn

Quality Inn

2.5 out of 5
190 Stadium St, Gateway North Plaza, Smyrna, DE
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $75 total per night from Dec 17 to Dec 18
$75 total
Dec 17 - Dec 18
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 ...
Everything was great!! Checked in with ease and staff was great!!

Reviewed on Nov 9, 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
$72 nightly
The price is $80 total per night from Nov 30 to Dec 1
$80 total
Nov 30 - Dec 1
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 ...
This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement.

Reviewed on Nov 9, 2025

Opens in a new windowRed Roof Inn & Suites Chestertown
Don't see what you're looking for?
See all available properties in Crumpton
View all properties
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 $75. 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 180 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

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Room was very clean. Staff friendly close to everything "
A verified traveler stayed at Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown

Explore More Ways to Travel with Travelocity