Searching for hotels in Chestertown? Compare room rates and reviews to find your ideal stay.

Where to Stay in Chestertown

Discover the most-visited places in Chestertown and find your best stay!

Chestertown Hotels Recommended for You

Check out our selection of great hotels in Chestertown.

5 star

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Business travel

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Breakfast

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Family friendly

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Hotels Near Famous Attractions in Chestertown

Check out these hotels located near popular sights in Chestertown

Rustic Charm

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Dynamite Hill Rd

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Walgreens

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Dunham Studios

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Frequently Asked Questions

  • What are the popular hotels in Chestertown?

    Chestertown has many popular hotels. Whether you're traveling for business or going on a vacation, Friends Lake Inn and The Fern Lodge are preferred hotels.

  • How much is the average rate for hotels in Chestertown?

    For hotels in Chestertown, the average price on weekdays is US$448, the average price on weekends (Friday–Saturday) is US$468.

  • Which hotels in Chestertown provide high-quality breakfasts?

    Friends Lake Inn and The Fern Lodge provide high-quality breakfast. Start your day with a delicious breakfast!

  • Which hotels in Chestertown provide fitness facilities?

    The Fern Lodge provides fitness facilities. Satisfy your fitness needs even while traveling!

  • Which hotels in Chestertown have swimming pools?

    Friends Lake Inn is a hotel with swimming pools. Stay at any of these hotels to enjoy a swimming pool!

  • Which hotels in Chestertown provide free Wi-Fi?

    Whether you're traveling on business or for vacation, Internet connection is an essential condition for travel. Friends Lake Inn and The Fern Lodge are popular hotels with free Wi-Fi.

  • Which hotels in Chestertown provide airport transfer services?

    Not familiar with Chestertown? Friends Lake Inn provides airport transfer services.

  • Which hotels in Chestertown have spas that are worth experiencing?

    Feel tired from traveling? Friends Lake Inn and The Fern Lodge provide highly rated spa services.

  • What hotel promotions are there in Chestertown?

    Trip.com provides various promotions and discounts for users all year round. You can check the promotions page to see what promotions are available on Trip.com.

Local Travel Info

Highest PriceUS$1,040
Lowest PriceUS$190
Number of Reviews 113
Number of hotels11
Average Price(Weekday Night)US$448
Average Price(Weekend Night)US$468

Chestertown Hotel Guide

If you want to stay at the best hotel in Chestertown, Trip.com is here to help! Book your hotel on Trip.com for an amazing travel experience. You can plan a day tour in Chestertown. Chestertown may not be a metropolis, but there are still great hotel options on Trip.com.

Though there is no civilian airport, it's still easy to take a bus or train to reach Chestertown. It's easy to travel by bus in Chestertown. There are buses to surrounding cities available every day.

Chestertown is not a tourist city, so the hospitality industry there isn't very well-developed. Many hotels can only be booked on location. Chestertown has high quality and low-priced hotels. You can spend one night at a nice hotel for only 279 USD. There are 1 five-star hotels in Chestertown at an average price of 196 USD per night. There are 1 four-star hotels in Chestertown at an average price of 518 USD per night. There are 1 two-star hotels in Chestertown at an average price of 122 USD per night. There are not many well-known chain hotels in Chestertown, but staying at a unique local hotel will make you feel at home. Conways Lake Manor in Chestertown is a favorite among Trip.com users. Many tourists also stay at The Fern Lodge.

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