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Find Chestertown motels from $57

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Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Lovely hotel, my favorite place to stay in Annapolis!"
Mary Ann 1-night trip
Posted 2 days ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about Chestertown

Chestertown Motels information

Number of reviews
2,188
Accommodation
11 Motels
Lowest Price
$57
Highest Price
$81

Frequently asked questions

What are the best Chestertown motels, based on reviews?
Driftwood Inn stands out as an excellent choice for travelers seeking value and comfort in Chestertown, MD. With its family-friendly design and thoughtful amenities, this motel is particularly appealing for those with children. Guests love the cozy beds and competitive pricing, making it an inviting option for families or anyone on a budget. The daily housekeeping ensures a clean and straightforward stay, while the child-friendly window design adds an extra layer of safety for younger guests.
What is the nightly rate for a motel in Chestertown?
You can find a great deal from $57 on Chestertown motels with Expedia. Typically, prices are higher during popular times – like weekends and holidays – while staying midweek is often cheaper. To find the best nightly rates on Chestertown motels, try to be flexible with travel dates, and sort search results by price from low to high.
Is it better to stay in a Chestertown motel or hotel?
Motels and Hotels have different perks. When you stay at a motel, you're likely to find free parking and an outdoor pool. Staying overnight at a motel, can be handy when requiring easy road access. You'll often have access to your room from outside, and directly from the parking lot. Hotels generally have room access from inside the building. Motels are also often less expensive than hotels. The word "motel" was coined in 1925 by the owner of the Milestone Mo-Tel in San Luis Obispo, California.

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