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Hotels Near Me in Chestertown

Stay Close to the City’s Top Sights and Connections in Chestertown, United States

Check-in
18Jun
Check-out
19Jun
Rooms and Guests2 Guests, 1 Room
Chestertown features the beautiful Chestertown Marina, where you can enjoy boat rentals and scenic views along the Sassafras River. Visit the historic Chester River Packet Company for local tours or relax at Wilmer Park with its picturesque walking paths. You'll find various accommodations, from waterfront hotels to cozy inns, each offering different experiences. This site presents a thoughtfully selected list of hotels with top amenities, perfect for finding your stay. Book in spring or fall for pleasant weather, and use local shuttles or bikes to explore effortlessly.
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1-4 out of 4
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
Quality Suites
8.0
Great
Quality Suites
Map1.3 mi from City Centre400 yd from Kent Plaza Shopping Center
FromUS$ 75 /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
3-star hotels
USD 68

Best hotels near me in Chestertown

Based on guest reviews over the last 12 months

Modern Comforts for Families:
Charming Waterfront Retreats:
Spacious Options for Groups:
Historic Elegance Awaits:

FAQs about hotels in Chestertown

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

Which hotel properties in Chestertown offer the best value for money?
The Comfort Inn & Suites Chestertown and Quality Suites typically offer competitive mid-range pricing, often starting around $90 USD per night, making them great choices for value. The Brampton 1860 is a premium property with a higher price point around $200 USD, appealing to those seeking a unique experience.
Which hotels in Chestertown are best for families with children?
Comfort Inn & Suites Chestertown is family-friendly, offering spacious rooms and proximity to parks. Driftwood Inn offers a cozy atmosphere and is a good choice for families seeking a quieter stay.
Which hotel in Chestertown has unique views or romantic amenities for couples?
Brampton 1860 offers attractive views and an intimate setting, making it popular for romantic getaways. Its historic charm adds to the experience for couples.
Which hotel properties in Chestertown are closest to popular landmarks?
Comfort Inn & Suites Chestertown and Quality Suites are conveniently located near downtown Chestertown, approximately 1.6 km from the Chestertown Historic District, providing easy access to local attractions.
What are the top-rated hotel properties in Chestertown based on guest reviews?
Brampton 1860 is highly rated for its unique historical charm and customer service, frequently receiving scores above 9/10 from guests. Comfort Inn & Suites also enjoys positive reviews for cleanliness and amenities.

Hotel Insights for Chestertown Travelers

This guide evaluates four hotels in Chestertown, providing key details to assist travelers in planning their stay, including peak seasons, pricing, and proximity to attractions.

Typical nightly prices range from $130 to $200.

There are 4 hotels available in Chestertown.

Peak travel seasons include spring and autumn.

Local taxes/fees are approximately 10% of the nightly rate.

Most hotels are within 2 kilometers of the Chester River and Historic District.

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