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Hotels in Chestertown, Maryland

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

Check-in
09Sept
Check-out
10Sept
Rooms and Guests2 Guests, 1 Room
Chestertown features attractions like the historic Chester River, the scenic Wilmer Park, and the lively Downtown area. You can explore art galleries, enjoy water sports at the Chester River Yacht and Country Club, or visit the historic District of Chestertown. The city offers a range of accommodations. You'll find charming bed and breakfasts, waterfront hotels, and family-friendly options with pools and breakfast included. This site provides a select list of top hotels based on reviews and amenities. Book ahead during festivals like the Chestertown Tea Party for the best rates.
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1-7 out of 7
Sort by:high popularity
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Driftwood Inn
7.0
Very good
Driftwood Inn Chestertown
MapNear Washington College300m
  • Rustic rooms with wood paneling
  • 24-hour front desk available
  • Pets allowed for travelers
  • 24-hour reception
  • Pet-friendly
  • Cable TV
Charming motel providing access to nature and relaxation
FromUS$ 57 /nightSelect
Brampton 1860
8.8
Great
Brampton 1860
MapProximity to Crow Vineyards500m
  • Adults-only historic hotel
  • Delicious gourmet dining options
  • Unique outdoor spaces available
  • Gourmet Dining
  • Private Gardens
  • Engaging Activities
Historic hotel offering personalized luxury experiences
FromUS$ 337 /nightSelect
Comfort Inn & Suites Chestertown
8.2
Great
Comfort Inn & Suites Chestertown
MapAccess to local attractions74km
  • Seasonal outdoor swimming pool
  • Complimentary American buffet breakfast
  • Fitness centre for guest use
  • Outdoor pool
  • Fitness centre
  • On-site dining
Hotel offering diverse dining and leisure amenities
FromUS$ 92 /nightSelect
Quality Suites
8.0
Great
Quality Suites
MapClose proximity to Washington College200m
  • Indoor heated pool access
  • Complimentary breakfast selection
  • Pet-friendly environment
  • Indoor pool
  • Pet-friendly
  • Bowling activities
Hotel offering unique amenities and accessible attractions
FromUS$ 75 /nightSelect
3 Mi To Washington College! Updated Home W/ Patio
3 Mi To Washington College! Updated Home W/ Patio
MapArtists' Gallery nearby4km
  • Updated home with outdoor dining area
  • Comfortable rooms with modern amenities
  • Convenient access to local attractions
  • Fully equipped kitchen
  • Outdoor terrace
  • Flat-screen TV
Holiday home with three bedrooms and patio area
Select
Walk To Historic Chestertown: Dog-Friendly Retreat
Walk To Historic Chestertown: Dog-Friendly Retreat
MapHistoric Chestertown attractions300m
  • Pet-friendly rooms with outdoor dining area
  • Two bedrooms and two bathrooms for comfort
  • Equipped kitchen with barbecue facilities
  • Outdoor dining
  • Pet-friendly
  • Fully equipped kitchen
Dog-friendly hotel with extensive local attractions
Select
Pet-Friendly Home On Chester River W/ Dock!
Pet-Friendly Home On Chester River W/ Dock!
MapArtists' Gallery2.2km
  • Private outdoor swimming pool
  • Four spacious bedrooms available
  • Terrace for outdoor dining
  • Outdoor Swimming Pool
  • Canoeing
  • Free Parking
Resort featuring a pet-friendly environment and private pool
FromUS$ 793 /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 793
⬇️ 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 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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