Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Check prices for these dates

Next weekend
19 Jun - 21 Jun
In two weeks
26 Jun - 28 Jun
In one month
10 Jul - 12 Jul
In two months
7 Aug - 9 Aug

Our top choices for Chestertown lodges

Premium Room

The Alpine Lodge

The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (682 reviews)
"Easy check in and good location in town. "
United States
James
The price is €121
includes taxes & fees
16 Jun - 17 Jun
The Alpine Lodge
Restaurant

North Creek Lodge at Gore Mountain

North Creek Lodge at Gore Mountain
3.0 star property
North Creek
7.8 out of 10, Good, (450 reviews)
"The owner is very friendly and helpful. Only s few minutes to the ski area Hotdog as part of breakfast was unusual Overall an ok place to stay "
United States
Vincent
The price is €126
includes taxes & fees
21 Jun - 22 Jun
North Creek Lodge at Gore Mountain
Exterior

Llama House ADK

Llama House ADK
2.5 star property
Wevertown
9.2 out of 10, Wonderful, (34 reviews)
"Dave was very considerate, enjoyed our stay"
United States
Daniel
The price is €167
includes taxes & fees
21 Jun - 22 Jun
Llama House ADK
Seasonal outdoor pool

Lodges At Cresthaven

Lodges At Cresthaven
4.0 star property
Lake George
9.4 out of 10, Exceptional, (608 reviews)
"The best place!"
United States
Allie
The price is €397
includes taxes & fees
18 Jun - 19 Jun
Lodges At Cresthaven
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.
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Top Chestertown Hotel Reviews

Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George

10/10 Excellent
"Great location, helpful staff and nice accommodations."
Amanda 1-night trip
Posted 1 hour ago
Howard Johnson by Wyndham Lake George

Find out more about Chestertown

Chestertown Lodges information

Number of reviews
1,774
Accommodation
28 Lodges
Lowest Price
€121
Highest Price
€397

Frequently asked questions

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Reserving lodges in Chestertown is as easy as clicking on your travel dates and picking a place that meets your needs. Use Expedia's filters to tailor your search results and find a dream getaway. Whether you're holidaying on a budget or have big bucks to splurge, you're sure to land awesome savings.
How can I find cheap lodges in Chestertown?
Expedia can help you search for cheap lodges in Chestertown. To book a terrific stay in a matter of clicks, use the filter tool to refine your search results by star rating, amenities and budget.
What is there to do in Chestertown near my lodge?
After you've settled into your lodge, venture out and explore the incredible things Chestertown has to offer. Loon Lake Beach is a great attraction to add to your to-do list.