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Motels in Chestertown

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Popular motels in Chestertown

Pricing data was last updated on September 12, 2025.
These are some of the motels in Chestertown with the highest demand.

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Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
Motel in Chestertown with free parking Along with a 24-hour front desk, this motel has express check-in and express check-out. Free WiFi in public areas and free self parking are also provided. Driftwood Inn offers 28 accommodations with coffee/tea makers and hair dryers. Premium satellite television is provided. Guests can make use of the in-room refrigerators and microwaves. Bathrooms include bathtubs or showers and complimentary toiletries. Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Housekeeping is provided daily.
Free Wi-Fi
Parking
4.5
Okay
166 reviews
Location
0.9 mi from city centre
$69
View Deal
All motels in Chestertown, MD

Highest rated Chestertown motels

Pricing data was last updated on September 12, 2025.
Find and compare prices for the top rated motels in Chestertown based on user reviews.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
0.9 mi from city centre
Free Wi-Fi
Parking
$69
Avg. per night
View Deal

Cheapest motels in Chestertown, MD

Pricing data was last updated on September 12, 2025.
These are some of the lowest-priced motels in Chestertown we've come across for the dates selected. Motels in Chestertown can be found for as low as $69 per night.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
0.9 mi from city centre
Free Wi-Fi
Parking
$69
Avg. per night
View Deal

Other accommodations in Chestertown

Pricing data was last updated on September 12, 2025.
Want more options for your trip to Chestertown? Find great deals on hotels, vacation rentals, hostels and more.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
0.9 mi from city centre
Free Wi-Fi
Parking
$69
Avg. per night
View Deal

Where to stay in Chestertown

Explore different neighborhoods and areas within Chestertown to find the perfect location for your stay. Map data was last updated on September 12, 2025.
Find a place to stay by zooming in or out on the map below. Hover over the pins to view the names of each motel, then click on a location name to view the deals.

Stay elsewhere in Chestertown, MD

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Vacation rentals in Chestertown, Maryland

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