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Hotels in Chestertown (Page 4)

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)
Extended Stay America Suites - Baltimore - Glen Burnie in Glen Burnie, USA

Extended Stay America Suites - Baltimore...

Hotel in Glen Burnie near Chestertown, Maryland , 104 Chesapeake Centre Ct
This Extended Stay America - Baltimore - Glen Burnie is located in Glen Burnie and especially designed for longer stays, with all rooms featuring a fu...
  • Parking
  • Pets allowed
  • Family rooms

Okay 169 Reviews 5.8

from $92.14 Show details »

Hyatt Place Baltimore Inner Harbor in Baltimore, USA

Hyatt Place Baltimore Inner Harbor

Hotel in Baltimore near Chestertown, Maryland , 511 South Central Avenue
Featuring an indoor swimming pool and an on-site restaurant, Hyatt Place Baltimore Inner Harbor is located in Baltimore.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Good 1006 Reviews 7.9

from $286.88 Show details »

Tru By Hilton Baltimore Harbor East in Baltimore, USA

Tru By Hilton Baltimore Harbor East

Hotel in Baltimore near Chestertown, Maryland , 411 S Central Avenue
Located in Baltimore and with Harbor East Marina reachable within 700 metres, Tru By Hilton Baltimore Harbor East provides concierge services, non-smo...
  • Parking
  • Pets allowed
  • Fitness centre
  • Allergy-free room
  • Kid-friendly buffet

Very good 2384 Reviews 8.6

from $208.82 Show details »

Courtyard by Marriott Baltimore Downtown/Inner Harbor in Baltimore, USA

Courtyard by Marriott Baltimore Downtown...

Hotel in Baltimore near Chestertown, Maryland , 1000 Aliceanna Street
Just 1 block away from Baltimore’s scenic waterfront, Courtyard Downtown/Inner Harbor is located a 10-minute walk from the National Aquarium.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Very good 388 Reviews 8.4

from $328.71 Show details »

Red Roof Inn & Suites Dover Downtown in Dover, USA

Red Roof Inn & Suites Dover Downtown

Motel in Dover near Chestertown, Maryland , 652 North Dupont Highway
This hotel is located 1 mile from Dover International Speedway and features free WiFi.
  • Parking
  • Pets allowed
  • Family rooms
  • Shower
  • Bath

Pleasant 567 Reviews 7.0

from $79.49 Show details »

Fairfield Inn & Suites by Marriott Dover in Dover, USA

Fairfield Inn & Suites by Marriott Dover

Hotel in Dover near Chestertown, Maryland , 655 North Dupont Highway
Located 1 mile from Dover Downs Hotel and Casino, this hotel offers free Wi-Fi.
  • Parking
  • Fitness centre
  • Family rooms
  • Tea/Coffee maker
  • Shower

Good 89 Reviews 7.9

from $139.33 Show details »

Best Western Plus Easton Inn & Suites in Easton, USA

Best Western Plus Easton Inn & Suites

Hotel in Easton near Chestertown, Maryland , 8708 Alicia Dr
Best Western Plus Easton Inn & Suites is set in Easton, 2.2 km from Academy of the Arts.
  • Parking
  • Fitness centre
  • Family rooms
  • Indoor pool
  • Swimming pool

Fabulous 495 Reviews 8.8

from $139.00 Show details »

Hilton Garden Inn Baltimore Inner Harbor in Baltimore, USA

Hilton Garden Inn Baltimore Inner Harbor

Hotel in Baltimore near Chestertown, Maryland , 625 South President Street
Located in the heart of Baltimores Harbor East neighbourhood and adjacent to vibrant Little Italy, this hotel provides state-of-the-art amenities and ...
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Good 300 Reviews 7.4

from $295.00 Show details »

Homewood Suites by Hilton Baltimore in Baltimore, USA

Homewood Suites by Hilton Baltimore

Hotel in Baltimore near Chestertown, Maryland , 625 South President Street
Situated in the heart of Baltimores Inner Harbor and close to area attractions, this all-suite hotel provides guests with many of the comforts of home...
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Good 221 Reviews 7.6

from $294.42 Show details »

Holiday Inn Express Hotel & Suites-North East, an IHG Hotel in North East, USA

Holiday Inn Express Hotel & Suites-North...

Hotel in North East near Chestertown, Maryland , 101 Hotel Plaza
Located off Interstate 95, this North East, Maryland hotel is 4.8-miles from Elk Neck State Forest.
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Very good 125 Reviews 8.4

from $119.20 Show details »

Baltimore Marriott Waterfront in Baltimore, USA

Baltimore Marriott Waterfront

Hotel in Baltimore near Chestertown, Maryland , 700 Aliceanna Street
This Baltimore hotel is located directly next to the Baltimore Harbor, in the Harbor East neighborhood.
  • Parking
  • Fitness centre
  • Breakfast in the room

Fabulous 824 Reviews 8.8

from $221.00 Show details »

Residence Inn Dover in Dover, USA

Residence Inn Dover

Hotel in Dover near Chestertown, Maryland , 600 Jefferic Boulevard
Within 2 miles from Dover International Speedway and Delaware State University, Residence Inn Dover has self catering guest rooms with free Wi-Fi.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Spa and wellness centre

Very good 105 Reviews 8.5

from $170.67 Show details »

Wyndham Garden Dover in Dover, USA

Wyndham Garden Dover

Hotel in Dover near Chestertown, Maryland , 561 N DuPont Hwy
Featuring 3-star accommodation, Wyndham Garden Dover is located in Dover, 26 km from Killens Pond Water Park and 1.2 km from Williams Park.
  • Parking
  • Fitness centre
  • Family rooms

Pleasant 278 Reviews 6.5

from $123.20 Show details »

Hampton Inn Baltimore/Glen Burnie in Glen Burnie, USA

Hampton Inn Baltimore/Glen Burnie

Hotel in Glen Burnie near Chestertown, Maryland , 6617 Ritchie Highway
This Glen Burnie hotel features free shuttle services to Baltimore Washington International Airport.
  • Parking
  • Pets allowed
  • Family rooms
  • Pay-per-view channels
  • TV

Good 305 Reviews 8.0

from $120.83 Show details »

La Quinta by Wyndham Baltimore South Glen Burnie in Glen Burnie, USA

La Quinta by Wyndham Baltimore South Gle...

Hotel in Glen Burnie near Chestertown, Maryland , 6323 Ritchie Highway
La Quinta Inn & Suites Baltimore South/Glen Burnie, 6 miles from downtown Baltimore, Maryland, features a garden.
  • Parking
  • Pets allowed
  • Fitness centre
  • Telephone
  • Air conditioning

Pleasant 938 Reviews 6.7

from $67.67 Show details »

Pier 5 Hotel Baltimore in Baltimore, USA

Pier 5 Hotel Baltimore

Hotel in Baltimore near Chestertown, Maryland , 711 Eastern Avenue
Boasting a scenic waterfront location close to area attractions, including the National Aquarium, this Baltimore hotel offers free local area shuttles...
  • Parking
  • Restaurant
  • Pets allowed

Good 343 Reviews 7.4

from $146.48 Show details »

Red Roof Inn Baltimore South Glen Burnie in Glen Burnie, USA

Red Roof Inn Baltimore South Glen Burnie

Hotel in Glen Burnie near Chestertown, Maryland , 6600 Ritchie Highway
This Glen Burnie hotel is within a 10-minute drive of Baltimore Washington International Airport.
  • Parking
  • Pets allowed
  • Fitness centre
  • Outdoor pool
  • Swimming pool

Okay 211 Reviews 5.8

from $76.95 Show details »

Holiday Inn Express Easton, an IHG Hotel in Easton, USA

Holiday Inn Express Easton, an IHG Hotel

Hotel in Easton near Chestertown, Maryland , 8561 Ocean Gateway Route 50
Holiday Inn Express Easton is located in Easton.
  • Parking
  • Fitness centre
  • Indoor pool
  • Swimming pool
  • Swimming Pool

Superb 138 Reviews 9.0

from $121.87 Show details »

Super 8 by Wyndham Dover in Dover, USA

Super 8 by Wyndham Dover

Motel in Dover near Chestertown, Maryland , 348 North Dupont Highway
Located on Silver Lake in Dover, Delaware, this hotel is 5 minutes from the Dover International Speedway and the Dover Downs Casino.
  • Parking
  • Telephone
  • Air conditioning
  • Hairdryer
  • Radio

Disappointing 197 Reviews 4.7

from $69.30 Show details »

Superlodge in Dover, USA

Superlodge

Hotel in Dover near Chestertown, Maryland , 246 N DuPont Hwy
Set in Dover, 3.1 km from Dover International Speedway, Superlodge offers accommodation with free WiFi and free private parking.
  • Parking

Passable 255 Reviews 5.6

from $121.67 Show details »

Sleep Inn & Suites Downtown Inner Harbor in Baltimore, USA

Sleep Inn & Suites Downtown Inner Harbor

Hotel in Baltimore near Chestertown, Maryland , 301 Fallsway
Located in a historic warehouse with a gym and free Wi-Fi, this eco-friendly Baltimore hotel is blocks from downtown Inner Harbor.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms

Pleasant 371 Reviews 6.1

from $119.21 Show details »

Comfort Inn & Suites in North East, USA

Comfort Inn & Suites

Hotel in North East near Chestertown, Maryland , 1 Center Drive
This North East hotel is off Interstate 95 and 3 miles from the Upper Bay Museum.
  • Parking
  • Pets allowed
  • Fitness centre
  • Tea/Coffee maker
  • Shower

Good 208 Reviews 7.4

from $106.48 Show details »

Days Inn by Wyndham Dover Downtown in Dover, USA

Days Inn by Wyndham Dover Downtown

Motel in Dover near Chestertown, Maryland , 272 North Dupont Highway
Located on Route 13 in Dover, Delaware, this hotel is just 5 minutes’ drive from Dover Downs Casino.
  • Parking
  • Fitness centre
  • Family rooms

Poor 297 Reviews 3.6

from $98.33 Show details »

Holiday Inn Express Baltimore-Downtown, an IHG Hotel in Baltimore, USA

Holiday Inn Express Baltimore-Downtown,...

Hotel in Baltimore near Chestertown, Maryland , 221 North Gay Street
Featuring spacious guestrooms furnished with flat-screen TVs and free wireless internet access, this downtown Baltimore hotel provides easy access to ...
  • Parking
  • Pets allowed
  • Fitness centre
  • Bath
  • Safety deposit box

Good 421 Reviews 7.5

from $113.00 Show details »

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

Staybridge Suites Baltimore - Inner Harb...

Hotel in Baltimore near Chestertown, Maryland , 17 Commerce Street
Located in Baltimore, 400 metres from National Aquarium in Baltimore, Staybridge Suites Baltimore - Inner Harbor boasts air-conditioned rooms with fre...
  • Parking
  • Pets allowed
  • Fitness centre
  • Kid-friendly buffet
  • Shower

Very good 2145 Reviews 8.6

from $175.20 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