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Hotels in Chestertown (Page 6)

Enjoy your stay and find the best Hotels in Chestertown at affordable prices

Searching for a hotel in Chestertown (Maryland)? You will find a wide selection of hotels in Chestertown and the surrounding region at great rates, starting from $52.97 per night. From cheap budget hotels to family hotels and premium hotels for business travel and more upscale. Choose a hotel for more info about the offer.

Hotels in Chestertown and region (50 miles)
Econo Lodge Easton Route 50 in Easton, USA

Econo Lodge Easton Route 50

Hotel in Easton near Chestertown, Maryland , 8175 Ocean Gateway
The newly renovated Econo Lodge Easton Route 50 offers easy access to Baltimore, Annapolis, Dover and Washington, D.C.
  • Parking

Pleasant 53 Reviews 6.8

from $92.56 Show details »

Holiday Inn Express Towson- Baltimore North, an IHG Hotel in Towson, USA

Holiday Inn Express Towson- Baltimore No...

Hotel in Towson near Chestertown, Maryland , 1100 Cromwell Bridge Road
Holiday Inn Express Towson- Baltimore North is just off I-695 and 16 miles from downtown Baltimore.
  • Parking
  • Fitness centre
  • Tea/Coffee maker
  • Shower
  • Bath

Very good 1154 Reviews 8.3

from $122.62 Show details »

DoubleTree by Hilton Hotel Annapolis in Annapolis, USA

DoubleTree by Hilton Hotel Annapolis

Hotel in Annapolis near Chestertown, Maryland , 210 Holiday Court
Offering a free shuttle service to attractions within a 8 km radius, this hotel is 4.8 km from Annapolis’s historic city centre.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Good 372 Reviews 7.9

from $124.44 Show details »

Baltimore Marriott Inner Harbor at Camden Yards in Baltimore, USA

Baltimore Marriott Inner Harbor at Camde...

Hotel in Baltimore near Chestertown, Maryland , 110 South Eutaw Street
This downtown Baltimore hotel is within a 3-minute drive of the Inner Harbor.
  • Parking
  • Restaurant
  • Bar
  • Fitness centre
  • Family rooms

Good 572 Reviews 7.8

from $152.15 Show details »

Hilton Baltimore Inner Harbor in Baltimore, USA

Hilton Baltimore Inner Harbor

Hotel in Baltimore near Chestertown, Maryland , 401 West Pratt Street
Offering direct access to the Baltimore Convention Center via a covered sky bridge and within walking distance of the Inner Harbor, this hotel offers ...
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Sauna

Good 514 Reviews 7.9

from $220.15 Show details »

SpringHill Suites by Marriott Baltimore Downtown Convention Center Area in Baltimore, USA

SpringHill Suites by Marriott Baltimore...

Hotel in Baltimore near Chestertown, Maryland , 100 North Eutaw Street
Situated in Baltimore and with Sports Legends Museum at Camden Yards reachable within 700 metres, SpringHill Suites by Marriott Baltimore Downtown Con...
  • Parking
  • Pets allowed
  • Fitness centre
  • Kid-friendly buffet
  • Electric vehicle charging station

Very good 873 Reviews 8.5

from $135.00 Show details »

Sutton Inn in Elkton, USA

Sutton Inn

Hotel in Elkton near Chestertown, Maryland , 405 East Pulaski Highway
This hotel is located off of Route 40 in Elkton, Maryland, a 15-minute drive from downtown Newark.
  • Parking
  • Pets allowed
  • Family rooms
  • Telephone
  • Air conditioning

Fabulous 152 Reviews 8.9

from $159.00 Show details »

Red Roof Inn Annapolis in Annapolis, USA

Red Roof Inn Annapolis

Motel in Annapolis near Chestertown, Maryland , 2520C Riva Road
Featuring 2-star accommodation, Red Roof Inn Annapolis is set in Annapolis, 37 km from Addison Road-Seat Pleasant and 42 km from Carroll Park.
  • Parking
  • Pets allowed
  • Allergy-free room

Good 176 Reviews 7.1

from $89.67 Show details »

Best Western Annapolis in Annapolis, USA

Best Western Annapolis

Hotel in Annapolis near Chestertown, Maryland , 2520 Riva Road
Located just 4 miles from the United States Naval Academy, this Annapolis hotel boasts a seasonal outdoor pool.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Allergy-free room

Good 559 Reviews 7.5

from $106.59 Show details »

Brexton Hotel in Baltimore, USA

Brexton Hotel

Hotel in Baltimore near Chestertown, Maryland
Located within 700 metres of The Walters Art Museum and less than 1 km of Baltimore - Penn Station, MD, Brexton Hotel provides rooms with air conditio...
  • Parking

Good 195 Reviews 7.0

from $88.00 Show details »

Hampton Inn Baltimore-Downtown-Convention Center in Baltimore, USA

Hampton Inn Baltimore-Downtown-Conventio...

Hotel in Baltimore near Chestertown, Maryland , 550 Washington Boulevard
Within walking distance to many of central Baltimores main sites, including Oriole Park at Camden Yards, this hotel provides comfortable accommodation...
  • Parking
  • Fitness centre
  • Family rooms
  • Indoor pool
  • Kid-friendly buffet

Very good 922 Reviews 8.5

from $301.86 Show details »

Hampton Inn Easton in Easton, USA

Hampton Inn Easton

Hotel in Easton near Chestertown, Maryland , 8058 Ocean Gateway
This hotel is located 1 mile from historic central Easton and features an indoor swimming pool and a daily hot breakfast.
  • Parking
  • Fitness centre
  • Indoor pool
  • Swimming pool
  • Swimming Pool

Good 125 Reviews 7.9

from $193.42 Show details »

The Wildset in Saint Michaels, USA

The Wildset

Hotel in Saint Michaels near Chestertown, Maryland , 209 North Talbot Street
Situated in Saint Michaels, 17 km from Academy of the Arts, The Wildset features accommodation with a restaurant, free private parking and a bar.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar

Superb 138 Reviews 9.2

from $339.00 Show details »

Best Western Chesapeake Bay North Inn in North East, USA

Best Western Chesapeake Bay North Inn

Hotel in North East near Chestertown, Maryland , 39 Elwoods Road
Located 1 mile from Interstate 95, Best Western Chesapeake Bay North Inn is within 13 miles of Newark, Delaware and the University of Delaware.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Allergy-free room

Good 126 Reviews 7.2

from $131.75 Show details »

Motel 6 Baltimore MD in Baltimore, USA

Motel 6 Baltimore MD

Motel in Baltimore near Chestertown, Maryland , 110 West North Avenue
Located in Baltimore, this Motel 6 is within 5 minutes’ drive of the University of Baltimore and Baltimore Museum of Art.
  • Parking
  • Pets allowed
  • Family rooms

Passable 356 Reviews 5.4

from $63.83 Show details »

Hampton Inn & Suites Annapolis in Annapolis, USA

Hampton Inn & Suites Annapolis

Hotel in Annapolis near Chestertown, Maryland , 124 Womack Drive
Located 11.2 km from historic Annapolis city centre and many popular area attractions, this hotel features a number of thoughtful on-site facilities a...
  • Parking
  • Pets allowed
  • Fitness centre
  • Outdoor pool
  • Kid-friendly buffet

Good 619 Reviews 7.9

from $100.02 Show details »

Best Bedroom Next to JHU in Baltimore, USA

Best Bedroom Next to JHU

Hotel in Baltimore near Chestertown, Maryland , 202 E 32nd St
Set in Baltimore, 500 metres from Baltimore Museum of Art, Best Bedroom Next to JHU offers rooms with air conditioning.
  • Shower
  • Bath
  • Air conditioning
  • Kitchenette
  • Free toiletries

Good 102 Reviews 7.3

from $69.00 Show details »

Extended Stay America Suites - Annapolis - Womack Drive in Annapolis, USA

Extended Stay America Suites - Annapolis...

Hotel in Annapolis near Chestertown, Maryland , 1 Womack Drive
This Extended Stay America - Annapolis - Womack Drive is located in Annapolis and especially designed for longer stays, with all rooms featuring a ful...
  • Pets allowed
  • Family rooms
  • Tea/Coffee maker
  • Shower
  • Bath

Passable 125 Reviews 5.5

from $62.00 Show details »

Country Inn & Suites by Radisson, Annapolis, MD in Annapolis, USA

Country Inn & Suites by Radisson, Annapo...

Hotel in Annapolis near Chestertown, Maryland , 2600 Housley Road
Located 4 miles from the scenic Annapolis waterfront, this hotel boasts an indoor pool and a daily hot breakfast.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 733 Reviews 8.5

from $117.94 Show details »

Mainstay Suites Dover in Dover, USA

Mainstay Suites Dover

Hotel in Dover near Chestertown, Maryland , 201 Stover Boulevard
This hotel is 2 miles from downtown Dover and is one mile from the Biggs Museum of American Art.
  • Parking
  • Pets allowed
  • Fitness centre
  • Indoor pool
  • Swimming pool

Good 187 Reviews 7.5

from $152.15 Show details »

Admiral Suites - Annapolis in Annapolis, USA

Admiral Suites - Annapolis

Hotel in Annapolis near Chestertown, Maryland , 120 Admiral Cochrane Drive
This Extended Stay America - Annapolis - Admiral Cochrane Drive is located in Annapolis and especially designed for longer stays, with all rooms featu...
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms

Okay 275 Reviews 5.9

from $75.60 Show details »

SpringHill Suites by Marriott Annapolis in Annapolis, USA

SpringHill Suites by Marriott Annapolis

Hotel in Annapolis near Chestertown, Maryland , 189 Admiral Cochrane Drive
Just 10 minutes’ drive from historic Annapolis, this hotel offers guests a complimentary breakfast buffet to start their day.
  • Parking
  • Fitness centre
  • Family rooms
  • Indoor pool
  • Kid-friendly buffet

Very good 425 Reviews 8.5

from $152.33 Show details »

Sonesta ES Suites Annapolis in Annapolis, USA

Sonesta ES Suites Annapolis

Hotel in Annapolis near Chestertown, Maryland , 170 Admiral Cochrane Drive
This all-suite Annapolis hotel offers a fully equipped kitchen, separate living room and work desk in every suite.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Outdoor pool

Very good 515 Reviews 8.3

from $159.89 Show details »

Courtyard by Marriott Annapolis in Annapolis, USA

Courtyard by Marriott Annapolis

Hotel in Annapolis near Chestertown, Maryland , 2559 Riva Road
This Courtyard by Marriott hotel, located in historic Annapolis, is a 10-minute drive to the US Naval Academy.
  • Fitness centre
  • Family rooms
  • Allergy-free room

Very good 191 Reviews 8.0

from $137.00 Show details »

Hilton Garden Inn Annapolis in Annapolis, USA

Hilton Garden Inn Annapolis

Hotel in Annapolis near Chestertown, Maryland , 305 Harry South Truman Parkway
Minutes from the heart of Annapolis city centre and the citys historic district, this hotel offers many modern amenities and facilities along with fri...
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Good 829 Reviews 7.7

from $132.83 Show details »

Number of Hotels in Chestertown 244
Number of guest ratings 374
Average price per night $164.97
Lowest price per night $52.97
Highest price per night $1.109.33

Most popular Hotels in Chestertown

The most popular Hotels in Chestertown based on average guest rating (Top 10).

Cheapest Hotels in Chestertown

The cheapest Hotels in Chestertown based on room rate per night (Top 10).

Most booked Hotels in Chestertown

The most booked Hotels in Chestertown based on popularity with guests (Top 10).

How to find the best hotel in Chestertown (Maryland)

Finding the best hotel in Chestertown depends on your individual needs and preferences. First, consider your budget. Deciding how much you are willing to spend can help you narrow down your search and avoid overspending. Keep in mind that higher prices may not always equate to better quality or value.

Next, think about the location. Do you want to stay in the heart of Chestertown, or would you prefer a quieter area outside of town? Consider factors like proximity to attractions, transportation, and safety when choosing a location.

After that, consider the type of hotel you want to stay in. Do you prefer a boutique hotel with personalized service, or a large chain hotel with more amenities? Think about whats most important to you, whether it is a pool, a gym, or a great restaurant.

It is also important to read reviews from other travelers to get an idea of the hotels reputation. Look for comments about cleanliness, service, and overall experience to get a better sense of what to expect.

Don't be afraid to contact the hotel directly with any questions or concerns. A good hotel should be happy to answer your questions and make your stay as comfortable as possible.

Hotels in Chestertown - which one to choose?

One of the most common types of hotels in Chestertown and surrounding region are budget or economy hotels, who offer affordable accommodation for travelers on a tight budget, and extended-stay hotels, which are designed for guests who need to stay for an extended period of time, such as business travelers or those relocating to a new city.

Another popular type of hotel is the boutique hotel. These hotels are smaller in size and typically feature unique and personalized decor and amenities, often designed to appeal to a specific target market or theme. Boutique hotels in Chestertown are often independently owned and operated, and they are known for their distinctive character and personalized service.

If you want the carefree package maybe the luxury hotel in Chestertown ist the right choice for you. These hotels are known for their high-end amenities and exceptional service, and are often located in prime locations such as city centers or scenic destinations. Luxury hotels typically feature upscale restaurants, fitness centers, spas, and other lavish facilities, and they are designed to cater to guests who are seeking a luxurious and indulgent experience.

Resort hotels are another common type of accommodation, particularly in tropical and beach destinations. These hotels offer a wide range of amenities, including pools, spas, restaurants, and outdoor activities such as water sports and golf. They are designed to provide guests with a complete vacation experience, with everything they need to relax and have fun in one location.

Accommodation data and pictures provided by Booking.com