Crumpton, MD

Travel Guide

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
$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
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Red Roof Inn & Suites Chestertown
Quality Inn Smyrna

Quality Inn Smyrna

2.5 out of 5
190 Stadium St, Gateway North Plaza Smyrna DE
$84 nightly
The price is $93 total per night from Nov 11 to Nov 12
$93 total
Nov 11 - Nov 12
Total with taxes and fees
Book a stay at this business-friendly hotel in Smyrna. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Quality 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
$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
Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
8/10 Very Good! (119 reviews)
"Stayed in October. Room was clean and had a great view of the water. No microwave or coffee in the room but it was always available at the end of the hall. Keyless entry was convenient . Cell service is terrible though had to go to the windows to have any service."

Reviewed on Oct 12, 2026

The Lodge at Great Oak Landing
See all 201 properties in Crumpton
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.
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
Book a stay at this family-friendly villa in Rock Hall. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Rock Hall Harbor and The Mainstay ...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville MD
Stay at this cottage in Earleville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Turkey Point Light and Elk Neck State Park are located ...
9.8/10 Exceptional! (72 reviews)
"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

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown MD
Book a stay at this golf apartment in Chestertown. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wilmer Park and Sumner Hall are ...
First Floor Studio Apartment in Historic Chestertown
See all properties in Crumpton
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.

Stay near popular Crumpton attractions

Crumpton Park

After visiting Crumpton Park, make a plan to see the other sights and activities in Crumpton.
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Frequently asked questions

When is the best time to visit Crumpton?
The best time to visit Crumpton is from September through November. For travelers seeking fewer crowds and potentially better value, the quieter months of March through May are a good option, offering a more relaxed experience for your trip.
What is Crumpton known for?
Crumpton is known for Crumpton Park, which stands as a central landmark within the city. Travelers can explore the park's grounds, offering a place for relaxation and activities. It serves as a focal point for visitors discovering the area.
What is a good itinerary length for Crumpton?
A good itinerary length for Crumpton is one day to fully explore Crumpton Park. Travelers can enjoy its natural beauty and points of interest. For a more leisurely visit or to revisit favorite spots within the park, an extended stay of two days would allow for a relaxed pace.
What are the top things to do in and around Crumpton?
In Crumpton, travelers can explore Crumpton Park, a natural area of interest.
Can I book a refundable hotel in Crumpton?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Crumpton by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Crumpton with Expedia?
Expedia makes it easier to plan your Crumpton trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Crumpton?
The best choice depends on your travel style. Hotels in Crumpton can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Crumpton trip on Expedia?
Once you've booked your Crumpton trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Crumpton trip?
Expedia offers customer support before, during, and after your Crumpton trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Crumpton?
If it's your first trip to Crumpton, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Crumpton hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Crumpton hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Crumpton

An aerial view of a town with a river, buildings, and surrounding greenery.

Chestertown

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