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Hotels in Chestertown, Maryland

Only Handpicked and Verified Accommodations for Your Stay in Chestertown, United States

Check-in
10Jun
Check-out
11Jun
Rooms and Guests2 Guests, 1 Room
Filter by:
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Star rating
Guest rating
Accommodation type
Price per night
Popular landmarks
Amenities
Services
Brands
1-3 out of 3
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Driftwood Inn
7.0
Very good
Driftwood Inn
Map1700 yd from City Centre300 yd from Kent Plaza Shopping Center
FromUS$ 57 /nightSelect
Brampton 1860
8.8
Great
Brampton 1860
Map1.5 mi from City Centre
FromUS$ 337 /nightSelect
Comfort Inn & Suites Chestertown
8.2
Great
Comfort Inn & Suites Chestertown
Map1.3 mi from City Centre400 yd from Kent Plaza Shopping Center
FromUS$ 92 /nightSelect

Price range for hotels in Chestertown

A world of accommodation options awaits, from budget-friendly stays to luxurious retreats, with prices suited to every traveler's dream vacation.

⬆️ The highest price
USD 337
⬇️ The lowest price
USD 57
💸 Average price for
5-star hotels
USD 306
4-star hotels
USD 83

Best hotels in Chestertown

Based on guest reviews over the last 12 months

Relaxation by the River:
Comfort and Convenience:
Historic Charm and Elegance:

FAQs about hotels in Chestertown

We hope that the answers to these questions will help you plan your trip

Which hotels in Chestertown are family-friendly?
The Comfort Inn & Suites Chestertown is particularly well-suited for families, offering spacious rooms and amenities like free breakfast and an indoor pool, ideal for keeping kids entertained.
What hotels in Chestertown offer unique views?
The Driftwood Inn provides scenic views of the Chester River, making it a great choice for guests looking for picturesque landscapes during their stay.
Which hotel near popular landmarks does Chestertown have?
The Comfort Inn & Suites Chestertown is located just a short drive from downtown Chestertown and is conveniently close to landmarks like the Historical Society and the Chester River waterfront.
What are the top-rated hotels in Chestertown based on guest reviews?
The Brampton 1860 consistently receives high ratings for its charming atmosphere and personalized service, making it a favorite among visitors.
Are there any budget hotel options in Chestertown?
For budget-conscious travelers, the Driftwood Inn offers competitive rates, starting from $90 USD per night, making it one of the more affordable options in Chestertown.

Essential Hotel Facts for Chestertown Travelers

This guide provides essential information about hotel accommodations in Chestertown, evaluating 3 notable properties to assist travelers in making informed decisions regarding their stay.

Typical nightly prices range from $120 to $250.

Three hotels are available, offering different styles.

Peak seasons are spring and fall, especially during events.

Local tax rate is approximately 6% on bookings.

Hotels are within 2 km of the waterfront and historic district.

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