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Hotels in Chestertown (Page 5)

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)
Renaissance Baltimore Harborplace Hotel in Baltimore, USA

Renaissance Baltimore Harborplace Hotel

Hotel in Baltimore near Chestertown, Maryland , 202 East Pratt Street
This hotel is across the street from Baltimore’s Inner Harbor.
  • Parking
  • Restaurant
  • Bar
  • Fitness centre
  • Breakfast in the room

Very good 1410 Reviews 8.2

from $247.57 Show details »

Days Inn by Wyndham Towson in Towson, USA

Days Inn by Wyndham Towson

Hotel in Towson near Chestertown, Maryland , 8712 Loch Raven Boulevard
This Towson, Maryland hotel is located just off Interstate 695 and boasts an outdoor pool and an on-site restaurant.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Kid-friendly buffet

Poor 451 Reviews 3.4

from $66.30 Show details »

Comfort Inn in Towson, USA

Comfort Inn

Hotel in Towson near Chestertown, Maryland , 8801 Loch Raven Boulevard
Situated in a suburban setting, the Comfort Inn hotel is accessible from Interstate 695 and features a fitness centre and seasonal outdoor pool.
  • Parking
  • Fitness centre
  • Tea/Coffee maker
  • Bath
  • TV

Okay 746 Reviews 5.7

from $83.13 Show details »

The Royal Sonesta Harbor Court Baltimore in Baltimore, USA

The Royal Sonesta Harbor Court Baltimore

Hotel in Baltimore near Chestertown, Maryland , 550 Light Street
The Royal Sonesta Harbor Court Baltimore offers the ideal waterfront location, across the street from the Maryland Science Center and Harborplace, and...
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Sauna

Very good 1469 Reviews 8.3

from $193.88 Show details »

Comfort Inn & Suites Baltimore Inner Harbor in Baltimore, USA

Comfort Inn & Suites Baltimore Inner Har...

Hotel in Baltimore near Chestertown, Maryland , 120 E Lombard Street
This modern and contemporary hotel is centrally located in the heart of Baltimore, just 100 metres from the Inner Harbor.
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Allergy-free room
  • Tea/Coffee maker

Passable 879 Reviews 5.3

from $143.53 Show details »

Hampton Inn & Suites Baltimore Inner Harbor in Baltimore, USA

Hampton Inn & Suites Baltimore Inner Har...

Hotel in Baltimore near Chestertown, Maryland , 131 East Redwood Street
This Maryland hotel is situated 2 blocks from Baltimores Historic Inner Harbor and the Baltimore Convention Center.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Telephone

Very good 482 Reviews 8.2

from $186.56 Show details »

SpringHill Suites by Marriott Baltimore Downtown/Inner Harbor in Baltimore, USA

SpringHill Suites by Marriott Baltimore...

Hotel in Baltimore near Chestertown, Maryland , 120 East Redwood Street
This Baltimore hotel is a 5 minute walk from Inner Harbor.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Allergy-free room

Very good 1189 Reviews 8.0

from $180.00 Show details »

Hyatt Regency Baltimore in Baltimore, USA

Hyatt Regency Baltimore

Hotel in Baltimore near Chestertown, Maryland , 300 Light Street
Situated in Baltimore’s Inner Harbor, this hotel boasts an on-site restaurant and lounge, as well as an outdoor swimming pool.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Good 1203 Reviews 8.0

from $224.43 Show details »

Residence Inn by Marriott Baltimore Downtown/ Inner Harbor in Baltimore, USA

Residence Inn by Marriott Baltimore Down...

Hotel in Baltimore near Chestertown, Maryland , 17 Light Street
Residence Inn Downtown is located next to Baltimore Convention Center and 2 blocks from the renowned Inner Harbor.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Very good 559 Reviews 8.0

from $185.67 Show details »

Sheraton Inner Harbor Hotel in Baltimore, USA

Sheraton Inner Harbor Hotel

Hotel in Baltimore near Chestertown, Maryland , 300 South Charles Street
Surrounded by some of Baltimores most popular sites and ideally connect to the Convention Center, this Inner Harbor hotel offers modern amenities and ...
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Good 303 Reviews 7.3

from $189.00 Show details »

Crowne Plaza Annapolis, an IHG Hotel in Annapolis, USA

Crowne Plaza Annapolis, an IHG Hotel

Hotel in Annapolis near Chestertown, Maryland , 173 Jennifer Road
This Annapolis hotel is 6.7 km from the U.S.
  • Parking
  • Restaurant
  • Bar
  • Fitness centre
  • Allergy-free room

Very good 541 Reviews 8.3

from $103.20 Show details »

Delta Hotels by Marriott Baltimore Inner Harbor in Baltimore, USA

Delta Hotels by Marriott Baltimore Inner...

Hotel in Baltimore near Chestertown, Maryland , 1 East Redwood Street
Well situated in Baltimore, Delta Hotels by Marriott Baltimore Inner Harbor offers air-conditioned rooms, a fitness centre, free WiFi and a restaurant...
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Good 386 Reviews 7.2

from $116.10 Show details »

Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel in Annapolis, USA

Holiday Inn Express Hotel & Suites Annap...

Hotel in Annapolis near Chestertown, Maryland , 2451 Riva Road, Hwy.50, Exit 22
Situated off Route 50, this hotel offers access to Baltimore and Washington D.C.
  • Parking
  • Fitness centre
  • Kid meals
  • Kid-friendly buffet
  • Tea/Coffee maker

Good 274 Reviews 7.7

from $103.20 Show details »

Candlewood Suites Baltimore - Inner Harbor, an IHG Hotel in Baltimore, USA

Candlewood Suites Baltimore - Inner Harb...

Hotel in Baltimore near Chestertown, Maryland , 101 North Charles Street
Set in the heart of Baltimore, Candlewood Suites Baltimore - Inner Harbor is a 7-minute walk from Lexington Market.
  • Parking
  • Pets allowed
  • Fitness centre

Good 1004 Reviews 7.6

from $128.43 Show details »

Kimpton Hotel Monaco Baltimore Inner Harbor, an IHG Hotel in Baltimore, USA

Kimpton Hotel Monaco Baltimore Inner Har...

Hotel in Baltimore near Chestertown, Maryland , 2 North Charles Street
This pet-friendly Baltimore hotel is located 10 minutes’ walk from the Inner Harbor and features an on-site restaurant and bar.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Good 539 Reviews 7.7

from $180.86 Show details »

Home2 Suites by Hilton Baltimore Downtown in Baltimore, USA

Home2 Suites by Hilton Baltimore Downtow...

Hotel in Baltimore near Chestertown, Maryland , 8 East Pleasant Street
Located in downtown Baltimore, this hotel is a 6-minute walk from the Walters Art Museum.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Tea/Coffee maker

Good 237 Reviews 7.1

from $106.52 Show details »

Lord Baltimore Hotel in Baltimore, USA

Lord Baltimore Hotel

Hotel in Baltimore near Chestertown, Maryland , 20 West Baltimore Street
Located in the city centre of Baltimore, this hotel is 643 metres to the Inner Harbor and is 965 metres drive to Oriole Park at Camden Yards.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Good 2027 Reviews 7.7

from $152.10 Show details »

Midtown Inn in Baltimore, USA

Midtown Inn

Hotel in Baltimore near Chestertown, Maryland , 723 Saint Paul Street
Situated in the heart of Baltimore, Marylands legendary Mid Town, and only moments away from many of the Nations most popular attractions, is where yo...
  • Street parking
  • Shower
  • TV
  • Air conditioning
  • Radio

Very poor 140 Reviews 2.8

from $80.00 Show details »

dover garden suites in Dover, USA

dover garden suites

Hotel in Dover near Chestertown, Maryland , 315 Martin Street
Located 2.4 km from Delaware State Visitor Center, dover garden suites offers a garden, a terrace and air-conditioned accommodation with a patio and f...
  • Parking
  • Pets allowed
  • Family rooms
  • Tea/Coffee maker
  • Shower

Good 78 Reviews 7.9

from $100.00 Show details »

Days Inn by Wyndham Baltimore Inner Harbor in Baltimore, USA

Days Inn by Wyndham Baltimore Inner Harb...

Hotel in Baltimore near Chestertown, Maryland , 100 Hopkins Place
A quick stroll from the Baltimore Convention Center and located in the heart of the scenic Inner Harbor area, Days Inn by Wyndham Baltimore Inner Harb...
  • Parking
  • Pets allowed
  • Fitness centre

Pleasant 684 Reviews 6.6

from $126.65 Show details »

Hotel Indigo Baltimore Downtown, an IHG Hotel in Baltimore, USA

Hotel Indigo Baltimore Downtown, an IHG...

Hotel in Baltimore near Chestertown, Maryland , 24 W Franklin Street
This hotel is located in Baltimore and is within a 5-minute walk of Mt Vernon Place Historic District.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Very good 518 Reviews 8.5

from $145.87 Show details »

The Tidewater Inn in Easton, USA

The Tidewater Inn

Hotel in Easton near Chestertown, Maryland , 101 East Dover Street
Located on Maryland’s scenic Eastern Shore, this historic Easton accommodation boasts an on-site restaurant and bar.
  • Parking
  • Restaurant
  • Bar
  • Fitness centre
  • Family rooms

Very good 123 Reviews 8.3

from $199.00 Show details »

Ulysses in Baltimore, USA

Ulysses

Hotel in Baltimore near Chestertown, Maryland , 2 East Read Street
Located 500 metres from The Walters Art Museum, Ulysses offers 5-star accommodation in Baltimore and features a bar.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar

Fabulous 460 Reviews 8.7

from $209.00 Show details »

Hotel Revival Baltimore in Baltimore, USA

Hotel Revival Baltimore

Hotel in Baltimore near Chestertown, Maryland , 101 W Monument Street
Situated in the Mt.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Fabulous 267 Reviews 9.0

from $157.47 Show details »

La Quinta by Wyndham Inner Harbor Downtown in Baltimore, USA

La Quinta by Wyndham Inner Harbor Downto...

Hotel in Baltimore near Chestertown, Maryland , 200 West Saratoga Street
Featuring 3-star accommodation, La Quinta by Wyndham Inner Harbor Downtown is set in Baltimore, 1.1 km from Sports Legends Museum at Camden Yards and ...
  • Pets allowed
  • Fitness centre
  • Bath
  • TV
  • Telephone

Passable 1073 Reviews 5.4

from $87.55 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