#15.0/5Updated May 2026 · verified reviews
The best hotels in Chestertown for 2026.
18 top-rated hotels in Chestertown, USA, ranked by verified guest reviews. Live prices, instant booking, free cancellation — same rates as Booking.com.
Search hotels in Chestertown →18top-rated hotels
5.0/5best guest score
0 feessame price as direct
Overview
Where to stay in Chestertown.
Looking for a hotel in Chestertown? We've ranked the 18 best-reviewed stays in the city so you can compare ratings, location, and price in one place. Every hotel below has verified guest reviews and shows the same nightly rate you'd pay on Booking.com or direct — search your dates to see live availability.
18top-rated hotels
8rated 4★ or higher
1,037verified guest reviews
3.5/5average guest score
Across the 18 best-reviewed hotels in Chestertown, 8 carry a 4-star rating or higher and together they hold 1,037 verified guest reviews. The highest-rated right now is Great Oak Manor at 5.0/5. Whether you want a central base for sightseeing or a quieter, better-value area, the list below lets you compare location, star rating and real guest scores side by side before you book — at the same nightly rate you'd pay on Booking.com.
Top picks
18 best hotels in Chestertown.
Ranked by verified guest rating. Tap any hotel to see live rates, photos and rooms.
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#34.4/5
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#180.0/5See every hotel in Chestertown
Filter by price, star rating, guest score and dates. Same prices as Booking.com, free cancellation on most rooms.
View live Chestertown prices →Good to know
Booking a hotel in Chestertown.
- Best time to book: rates in Chestertown are usually lowest around 3–6 weeks out; weekends and local events push prices up, so lock in early for peak dates.
- Where to stay: central districts suit first-time visitors and sightseeing, while areas a little further out trade some walkability for noticeably better value.
- Free cancellation: most Chestertown hotels offer it up to check-in — filter for flexible rates if your plans aren't locked in yet.
- No price markup: every rate here matches Booking.com and Expedia, so you're comparing on location and quality, not hidden fees.
FAQ
Hotels in Chestertown — your questions.
What are the best hotels in Chestertown?
The top-rated hotel in Chestertown right now is Great Oak Manor (5.0/5 from 376 verified reviews). This page ranks 18 of the best-reviewed hotels in Chestertown, USA, updated for 2026.
How much does a hotel in Chestertown cost?
Nightly prices in Chestertown vary by season, location, and star rating. IMPT shows live rates that match Booking.com and Expedia — search your dates to see the current price for any hotel on this page.
Which area of Chestertown is best to stay in?
It depends on your trip: central districts suit first-time visitors and sightseeing, while quieter neighbourhoods offer better value. Every hotel below shows its exact location so you can pick what fits your plans.
Can I book a hotel in Chestertown with free cancellation?
Yes — most hotels in Chestertown offer free cancellation up to check-in. Filter for free-cancellation rates when you search your dates.
Are these Chestertown hotels good for families?
Many of the Chestertown hotels listed include family rooms, and you can set the number of guests and rooms when you search. Each listing shows star rating and verified guest scores to help you choose.
Find your hotel in Chestertown.
18 top-rated stays · live prices · free cancellation.
Start your Chestertown search →Follow IMPT