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Hotels in Chestertown (Page 2)

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)
The Inn at Chesapeake Bay Beach Club in Stevensville, USA

The Inn at Chesapeake Bay Beach Club

Hotel in Stevensville near Chestertown, Maryland , 180 Pier One Road
Located in Stevensville, 27 km from Annapolis Harbor, The Inn at Chesapeake Bay Beach Club provides accommodation with a seasonal outdoor swimming poo...
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Fitness centre

Superb 85 Reviews 9.2

from $283.00 Show details »

Super 8 by Wyndham Baltimore/Essex Area in Essex, USA

Super 8 by Wyndham Baltimore/Essex Area

Hotel in Essex near Chestertown, Maryland , 98 Stemmers Run Road
Located off Interstate 695, this Essex, Maryland hotel is just a 20-minute drive from downtown Baltimore.
  • Parking
  • Family rooms

Passable 220 Reviews 5.3

from $96.00 Show details »

Hilton Garden Inn Aberdeen in Aberdeen, USA

Hilton Garden Inn Aberdeen

Hotel in Aberdeen near Chestertown, Maryland , 1050 Beards Hill Road
Located off Interstate 95, this hotel is a 15-minute drive to the Aberdeen Proving Ground.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Very good 90 Reviews 8.0

from $176.07 Show details »

Super 8 by Wyndham Aberdeen MD in Aberdeen, USA

Super 8 by Wyndham Aberdeen MD

Hotel in Aberdeen near Chestertown, Maryland , 1008 Beards Hill Road
Just off Interstate 95 and a 15-minute drive from the Aberdeen Proving Grounds, this motel offers a continental breakfast and rooms equipped with micr...
  • Parking
  • Pets allowed

Pleasant 176 Reviews 6.0

from $56.70 Show details »

Days Inn by Wyndham Aberdeen in Aberdeen, USA

Days Inn by Wyndham Aberdeen

Hotel in Aberdeen near Chestertown, Maryland , 783 West Belair Avenue
Located close to Interstate 95, this hotel features free Wi-Fi, an outdoor pool, and rooms that offer a microwave and a refrigerator.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Kid meals

Good 668 Reviews 7.0

from $59.97 Show details »

Holiday Inn Express Aberdeen-Chesapeake House, an IHG Hotel in Aberdeen, USA

Holiday Inn Express Aberdeen-Chesapeake...

Hotel in Aberdeen near Chestertown, Maryland , 1007 Beards Hill Road
Located off Highway 95, this Aberdeen hotel offers classically furnished rooms equipped with free Wi-Fi, a flat-screen TV and a DVD player.
  • Parking
  • Fitness centre
  • Family rooms
  • Indoor pool
  • Swimming pool

Very good 163 Reviews 8.4

from $131.20 Show details »

Hampton Inn & Suites By Hilton Baltimore/Aberdeen, Md in Aberdeen, USA

Hampton Inn & Suites By Hilton Baltimore...

Hotel in Aberdeen near Chestertown, Maryland , 795 West Bel Air Avenue
Hampton Inn & Suites By Hilton Baltimore/Aberdeen, Md offers accommodation in Aberdeen.
  • Parking
  • Pets allowed
  • Kid meals
  • Kid-friendly buffet

Fabulous 161 Reviews 8.8

from $159.87 Show details »

La Quinta by Wyndham Aberdeen-APG in Aberdeen, USA

La Quinta by Wyndham Aberdeen-APG

Hotel in Aberdeen near Chestertown, Maryland , 793 West Bel Air Avenue
Located close to Interstate 95, this Aberdeen hotel offers free Wi-Fi and rooms equipped with cable TV and a work desk.
  • Parking
  • Pets allowed
  • Fitness centre
  • Outdoor pool
  • Swimming pool

Very good 527 Reviews 8.6

from $97.30 Show details »

Red Roof Inn Aberdeen in Aberdeen, USA

Red Roof Inn Aberdeen

Motel in Aberdeen near Chestertown, Maryland , 988 Hospitality Way
Located just off Interstate 95, this hotel is 2 miles from the Aberdeen Proving Grounds.
  • Parking
  • Pets allowed

Okay 462 Reviews 5.9

from $69.00 Show details »

Travelodge by Wyndham Aberdeen in Aberdeen, USA

Travelodge by Wyndham Aberdeen

Motel in Aberdeen near Chestertown, Maryland , 820 West Bel Air Avenue
This hotel is 1.7 miles from downtown Aberdeen, Maryland and 4 miles from Ruggles Golf Course.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Family rooms

Pleasant 359 Reviews 6.5

from $71.25 Show details »

Comfort Inn & Suites Aberdeen in Aberdeen, USA

Comfort Inn & Suites Aberdeen

Hotel in Aberdeen near Chestertown, Maryland , 980 Hospitality Way
Comfort inn and Suites Aberdeen offers air-conditioned rooms and free parking.
  • Restaurant
  • Pets allowed
  • Fitness centre
  • Outdoor pool
  • Kid-friendly buffet

Good 242 Reviews 7.5

from $105.40 Show details »

Fairfield by Marriott Inn & Suites Aberdeen in Aberdeen, USA

Fairfield by Marriott Inn & Suites Aberd...

Hotel in Aberdeen near Chestertown, Maryland , 907 Barnett Lane
Featuring 3-star accommodation, Fairfield by Marriott Inn & Suites Aberdeen is located in Aberdeen, 47 km from Clifton Park and 48 km from Towson Univ...
  • Toilet
  • Trash cans
  • Sofa bed
  • Hearing accessible

Fabulous 112 Reviews 8.9

from $210.00 Show details »

Holiday Inn Express - White Marsh, an IHG Hotel in White Marsh, USA

Holiday Inn Express - White Marsh, an IH...

Hotel in White Marsh near Chestertown, Maryland , 10542 Philadelphia Road
Providing free WiFi, Holiday Inn Express - White Marsh, an IHG Hotel is located in White Marsh, 19 km from Towson University and 19 km from Clifton Pa...

Superb 408 Reviews 9.2

from $107.00 Show details »

Home2 Suites by Hilton Baltimore/White Marsh in White Marsh, USA

Home2 Suites by Hilton Baltimore/White M...

Hotel in White Marsh near Chestertown, Maryland , 10465 Philadelphia Road
Located 3 minutes’ drive from Interstate 95, this hotel in White Marsh, Maryland is 12 miles from the Baltimore city centre.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 446 Reviews 8.1

from $109.65 Show details »

Residence Inn Aberdeen at Ripken Stadium in Aberdeen, USA

Residence Inn Aberdeen at Ripken Stadium

Hotel in Aberdeen near Chestertown, Maryland , 830 Long Drive
Less than a mile from the HEAT Center and Aberdeen Proving Ground, this hotel provides an indoor pool and an exercise room.
  • Parking
  • Restaurant
  • Bar
  • Fitness centre
  • Family rooms

Fabulous 17 Reviews 8.8

from $160.65 Show details »

Courtyard Aberdeen at Ripken Stadium in Aberdeen, USA

Courtyard Aberdeen at Ripken Stadium

Hotel in Aberdeen near Chestertown, Maryland , 830 Long Drive
Located just off Interstate 95 and neighbouring Ripken Stadium, Courtyard Aberdeen offers an indoor pool area and onsite fitness facilities.
  • Parking
  • Restaurant
  • Bar
  • Fitness centre
  • Family rooms

Good 31 Reviews 7.5

from $157.82 Show details »

Super 8 by Wyndham Havre De Grace Aberdeen Area in Havre de Grace, USA

Super 8 by Wyndham Havre De Grace Aberde...

Hotel in Havre de Grace near Chestertown, Maryland , 929 Pulaski Highway
This hotel is 5 minutes from downtown Havre de Grace, Maryland and Susquehanna Museum.
  • Parking
  • Family rooms

Pleasant 348 Reviews 6.2

from $60.63 Show details »

Hilton Garden Inn White Marsh in White Marsh, USA

Hilton Garden Inn White Marsh

Hotel in White Marsh near Chestertown, Maryland , 5015 Campbell Boulevard
Situated a short drive from Baltimore city centre, this suburban hotel offers numerous free amenities along with spacious accommodation and many moder...
  • Parking
  • Restaurant
  • Bar
  • Fitness centre
  • Family rooms

Good 320 Reviews 7.2

from $121.27 Show details »

Hampton Inn Baltimore/White Marsh in White Marsh, USA

Hampton Inn Baltimore/White Marsh

Hotel in White Marsh near Chestertown, Maryland , 8225 Town Center Drive
This conveniently located hotel is only seconds from motorway I-95 as well as the White Marsh Town Shopping Center, and offers many free amenities alo...
  • Parking
  • Fitness centre
  • Family rooms
  • Outdoor pool
  • Swimming pool

Pleasant 325 Reviews 6.7

from $109.86 Show details »

WoodSpring Suites Baltimore White Marsh - Nottingham in White Marsh, USA

WoodSpring Suites Baltimore White Marsh...

Hotel in White Marsh near Chestertown, Maryland , 4985 Mercantile Rd.
Set in White Marsh, within 18 km of Towson University and 18 km of Clifton Park, WoodSpring Suites Baltimore White Marsh - Nottingham offers accommoda...
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Private bathroom

Disappointing 469 Reviews 5.0

from $79.00 Show details »

Fairfield by Marriott Inn & Suites Middletown in Middletown, USA

Fairfield by Marriott Inn & Suites Middl...

Hotel in Middletown near Chestertown, Maryland , 411 Merrimac Avenue
Fairfield by Marriott Inn & Suites Middletown is situated in Middletown, 28 km from Tennis Court and 28 km from University of Delaware.
  • Electric vehicle charging station

Superb 133 Reviews 9.0

from $138.33 Show details »

Residence Inn Baltimore White Marsh in Baltimore, USA

Residence Inn Baltimore White Marsh

Hotel in Baltimore near Chestertown, Maryland , 4980 Mercantile Road
Located off I-95 at exit 67B, this hotel in Baltimore is just a few minutes’ drive from Baltimores Inner Harbor.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Outdoor pool

Very good 132 Reviews 8.3

from $121.14 Show details »

Country Inn & Suites by Radisson, Baltimore North, MD in White Marsh, USA

Country Inn & Suites by Radisson, Baltim...

Hotel in White Marsh near Chestertown, Maryland , 8825 Yellow Brick Road
Located 20.9 km from Inner Harbor in Baltimore, Maryland and near several corporate offices, this hotel offers a grab-and-go breakfast bags.
  • Parking
  • Fitness centre
  • Family rooms
  • Allergy-free room
  • Indoor pool

Pleasant 433 Reviews 6.7

from $90.64 Show details »

Fairfield Inn & Suites White Marsh in Baltimore, USA

Fairfield Inn & Suites White Marsh

Hotel in Baltimore near Chestertown, Maryland , 8477 Cordon Way
Fairfield Inn White Marsh offers contemporary accommodation 14 miles north of Baltimore.
  • Parking
  • Fitness centre
  • Swimming pool
  • Swimming Pool
  • Telephone

Very good 250 Reviews 8.1

from $100.03 Show details »

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

Holiday Inn Express & Suites - Middletow...

Hotel in Middletown near Chestertown, Maryland , 315 Auto Park Dr
Featuring 3-star accommodation, Holiday Inn Express & Suites - Middletown, an IHG Hotel is located in Middletown, 35 km from Old Dutch House and 43 km...
  • Parking
  • Fitness centre
  • Indoor pool
  • Kid-friendly buffet
  • Swimming pool

Fabulous 212 Reviews 8.8

from $111.20 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