Chestertown Hotels

THE 10 BEST Hotels in Chestertown 2024

Chestertown Hotels

and Places to Stay
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25 mi

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13 properties in Chestertown
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  • Best Value
    Properties ranked using exclusive Tripadvisor data, including traveler ratings, confirmed availability from our partners, prices, booking popularity and location, as well as personal user preferences and recently viewed hotels.
  • Traveler Ranked
    Highest rated hotels on Tripadvisor, based on traveler reviews.
  • Distance to city center
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Bed and Breakfast
flobow3648
flobow3648
@flobow3648
5.0 of 5 bubblesReviewed on Jun 4, 2021
Brampton Inn
"The cottage was spacious with a nice kitchen, large bedroom and separate bath."
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#1 Best Value of 13 places to stay in Chestertown
Charming hotel featuring beautiful front porch, outstanding breakfast, modern bathroom amenities, comfortable rooms, serene atmosphere, and warm, welcoming common areas.
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Inn
#2 Best Value of 13 places to stay in Chestertown
Historic property with stunning bay views, intimate atmosphere, and well-appointed rooms. Serene setting with Adirondack chairs, fire pit, and various outdoor activities.
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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#3 Best Value of 13 places to stay in Chestertown
Spacious, quiet rooms with comfortable beds, ideal for groups. Features attentive staff, well-stocked breakfast, and large conference rooms. Undergoing renovations for an enhanced stay.
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Bed and Breakfast
solomonsimonson
solomonsimonson
@KDSinDC
5.0 of 5 bubblesReviewed on Oct 21, 2021
All I could ask for in a B&B
"Very comfortable and quiet room."
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#4 Best Value of 13 places to stay in Chestertown
Beautifully restored historic inn with modern amenities, spacious rooms, and charming colonial atmosphere. Ideal central location, walkable to shops and waterfront. Highly praised breakfast.
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
No other properties are available in Chestertown. View nearby results below.
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Bed and Breakfast
Southern MD Traveller
Southern MD Traveller
@SouthernMDTraveller
5.0 of 5 bubblesReviewed on Mar 13, 2023
Wonderful First Time Stay at the Crow Farmstay B&B!
"It's a large room, has ample seating and storage space, and a comfortable queen sized bed."
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#1 Best Value of 1 place to stay in Kennedyville
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Bed and Breakfast
#3 Best Value of 9 places to stay in Rock Hall
Scenic hotel offering stunning water views, screened balconies, and marina access. Resort-like atmosphere with amenities including pool, yard games, complimentary kayaks, bikes, and paddleboards.
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Motel
Karen M
Karen M
@Y7435NQkarenm
5.0 of 5 bubblesReviewed on May 9, 2023
Great spot on Rock Hall
"Super charming motel!! Our room was clean, comfortable and cute!"
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#1 Best Value of 1 place to stay in Rock Hall
Recently renovated motel in peaceful marina setting. Clean, delightful rooms with retro-style appliances & flat-screen TVs. Lovely picnic area featuring hammocks, fire pit, and outdoor seating. Free rental bikes available.
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Bed and Breakfast
#2 Best Value of 9 places to stay in Rock Hall
Charming hotel with delicious homemade food, including vegetarian options. Highly recommended for relaxing getaways. Features cozy sitting area, marina views, and complimentary breakfast.
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Inn
#1 Best Value of 9 places to stay in Rock Hall
Charming inn with friendly resident dogs, beautiful grounds, and well-appointed cottages. Offers vouchers for nearby coffee shop, cozy main house, and luxurious amenities like fireplaces and jacuzzis.
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Showing results 1-30 of 30

Chestertown Hotels Information

Hotels in Chestertown

13

Hotels Prices From

$69

Hotels Reviews

2,182

Hotels Photos

1,083

Travel high season

Mar - May

Travel low season

Dec - Feb

High season avg price

$157

Low season avg price

$101
Not sure when to visit?
Price trends, weather and things to do can help you make a decision.
Season
Avg. price/night
Avg. temperature
Avg. precipitation
Dec - Feb
Avg. price/night
$99
LOWEST
$73$349
Avg. temperature
32ºF
COLDEST
13ºF102ºF
Avg. precipitation
33in
DRIEST
27 in57 in
Mar - May
Avg. price/night
$166
HIGHEST
$73$349
Avg. temperature
57ºF
13ºF102ºF
Avg. precipitation
37in
27 in57 in
Jun - Aug
Avg. price/night
$137
$73$349
Avg. temperature
78ºF
WARMEST
13ºF102ºF
Avg. precipitation
46in
WETTEST
27 in57 in
Sep - Nov
Avg. price/night
$137
$73$349
Avg. temperature
59ºF
13ºF102ºF
Avg. precipitation
46in
27 in57 in
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Chestertown. Select dates and complete search for nightly totals inclusive of taxes and fees.

Hotels near the sights

  • MassoniArt Gallery
    Respected by artists & collectors throughout the Mid-Atlantic region for over 30 years. For over 30 years, the Carla Massoni Gallery has worked in collaboration with architects, developers, interior design firms, art consultants, and non-profit organizations to bring art to the workplace. We have been honored to work with the US State Department’s Art in Embassies Program placing our artists work in American embassies throughout the world. We have placed works of art in SoHo lofts, New Jersey pharmaceutical companies, Delaware corporations, Baltimore non-profits, and Washington, DC law firms and associations. We provide a conduit for artists to interact with the business community by arranging opportunities for their work to appear in journals, newsletters and national publications.
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  • Historical Society of Kent County
    The Historical Society of Kent County, Maryland, is a non-profit organization dedicated to the collection and preservation of artifacts, documents, and information that aid in the interpretation of all aspects of Kent County’s history. The Society shares this information through its research library, museum space, programs, publications and website in order to foster a knowledge and understanding of the shared heritage of the community. The Society supports and encourages the preservation of historic buildings and sites throughout Kent County.
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  • Garfield Center for the Arts at the Prince Theatre
    Since its inception in 2002, the Prince Theatre Foundation has enjoyed success in various community endeavors: - Producing top of the line theatrical and musical productions - Providing quality educational, enriching experiences in the arts for children and adults - Partnering with over a dozen community organizations Recognized and valued as a unique community center for the arts.
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  • Art on High
    The Gallery at Rock Hall is a Contemporary and Modern collection of artists from near and far. We have a small collector's corner for those who search for the obscure yet valuable. Our eclectic collection is hand picked and curated with passion and a love for color and individuality. We welcome you to pay us a visit and enjoy paintings, photography, jewelry and sculpture.
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  • Book Plate
    Read more
Frequently Asked Questions about Chestertown hotels

Popular hotels close to Ronald Reagan National Airport include Hilton Arlington National Landing, Residence Inn Arlington Capital View, and Renaissance Arlington Capital View Hotel. See the full list: Hotels near Ronald Reagan National Airport.

The above hotel descriptions were created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for any of the above hotel descriptions. Please read full traveler reviews for more details and information. If you believe something in one of these AI-generated descriptions is inaccurate, please share your feedback.
Reviews are the subjective opinion of Tripadvisor members and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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