Hotels in Chestertown

Find the Cheap Chestertown Hotels

Enter your dates for the latest hotel rates and availability.

Swipe up to view more
Filter by:
Hotel Star Rating
≤2345
Popular Filters
Amazing 4.5+Great 4.0+Good 3.5+Pleasant 3.0+

We found these top-rated hotels near Chestertown for you

Choose your travel dates to see the latest prices and deals.
Most Booked
Lowest Price
Closest to Downtown
Highest Rated
See All Hotels Near Chestertown

Hotels near must-see attractions in Chestertown

Select from our curated hotels in Chestertown and enhance your visit with convenient access to nearby attractions.
Kent County Hotels in Chestertown

Kent County

8.0km from Chestertown
Learn More
Red Roof Inn & Suites Chestertown Hotels in Chestertown

Red Roof Inn & Suites Chestertown

Hotel in Chestertown
Red Roof Inn & Suites Chestertown, Maryland is a pet-friendly, family-friendly discount hotel. This hotel is close to Washington College, Chestertown Marina, Wilmer Park, Chesapeake Farms Wildlife Habitat Tour as well as numerous historical sites and museums such as Chestertown Electric , Historical Society-Kent County, Sumner Hall, Kent County Museum, Rock Hall Marine Restoration & Heritage Center, and the Waterman’s Museum. Red Roof Inn & Suites Chestertown features interior corridors, and a guest coin laundry. All rooms at this Red Roof Inn & Suites offer free Wi-Fi, a flat screen TV, microwave, mini-fridge, in-room coffee maker, hair dryer, iron & ironing board, desk, free in-room safe and a free expanded cable package featuring HBO. Experience our coffeehouse-style coffee and tea. One well-behaved family pet per room is welcome at Red Roof Inn & Suites Chestertown.
Show More
3.6/5
97 review
Price per night from:IDR 1,223,310
Mariner's Motel Hotels in Rock Hall

Mariner's Motel

Hotel in Rock Hall
Located in Rock Hall, Mariners Motel is near the bay, a 3-minute walk from Rock Hall Harbor and 13 minutes by foot from Ferry Park. This motel is 0.7 mi (1.1 km) from The Mainstay and 6.5 mi (10.5 km) from Eastern Neck National Wildlife Refuge. Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this motel include complimentary wireless internet access, a picnic area, and charcoal grills. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 12 guestrooms featuring refrigerators. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have shower/tub combinations and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.
Show More
4.6/5
Outstanding29 review
Price per night from:IDR 2,322,064
Holiday Inn Express Hotel & Suites Chestertown Hotels in Chestertown

Holiday Inn Express Hotel & Suites Chestertown

Hotel in Chestertown
When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical Society of Kent County Maryland. This hotel is 1.6 mi (2.6 km) from River Arts Chestertown and 5.9 mi (9.6 km) from Rolphs Wharf Marina.Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and a fireplace in the lobby. This hotel also features a banquet hall and a vending machine.A complimentary full breakfast is served on weekdays from 6:30 AM to 9:30 AM.Featured amenities include a business center, a 24-hour front desk, and laundry facilities. Free self parking is available onsite.Make yourself at home in one of the 81 guestrooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature designer toiletries and hair dryers. Conveniences include desks and microwaves, as well as phones with free local calls.
Show More
4.1/5
Very Good97 review
Price per night from:IDR 1,895,018
Edgewood Hotels in Chestertown

Edgewood

29.5km from Chestertown
Learn More
Quality Inn & Suites Bel Air I-95 Exit 77A Hotels in Edgewood

Quality Inn & Suites Bel Air I-95 Exit 77A

Hotel in Edgewood
Located in Edgewood, Quality Inn & Suites Bel Air I-95 Exit 77A is within a 10-minute drive of CopperPlex and Cedar Lane Regional Park. This hotel is 9.8 mi (15.7 km) from Ripken Stadium. A complimentary buffet breakfast is served on weekdays from 6:00 AM to 9:00 AM and on weekends from 7:00 AM to 10:00 AM. Featured amenities include a 24-hour front desk and an elevator. Free self parking is available onsite. Make yourself at home in one of the 104 guestrooms featuring refrigerators and LED televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Bathrooms with shower/tub combinations are provided. Conveniences include desks and microwaves, and housekeeping is provided on request.
Show More
3.9/5
76 review
Price per night from:IDR 834,075
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A Hotels in Edgewood

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Hotel in Edgewood
The La Quinta Inn and Suites by Wyndham Bel Air/I-95 Exit 77A has been awarded the 2018 TripAdvisor Certificate of Excellence award Looking for hotels in Edgewood Maryland. The La Quinta Inn and Suites by Wyndham Bel Air/I-95 Exit 77A is conveniently located off I-95 at Exit 77A offering convenient access to all there is to see and do in Edgewood Maryland. Our perfectly planted hotel near Baltimore Inner Harbor and Aberdeen Proving Grounds is just a short drive from these nearby attractions. The La Quinta Inn and Suites by Wyndham Bel Air/I-95 Exit 77A is near Peach Bottom Atomic Power Plant and offers the perfect location for contractors visiting Peach Bottom. Shopping dining and entertainment venues are within easy reach thanks to the hotels close proximity to local and downtown attractions like Baltimore Inner Harbor. Choose from a variety of restaurants such as Bonefish Grill Outback Steakhouse Red Lobster and many more. Shop at nearby Harford Mall or the Avenue at White Marsh before heading to a game at Ripken Stadium or Cedar Lane Regional Park. Unlike other Edgewood hotels we spoil you rotten with luxuries and amenities. Take advantage of our Free Bright Side Breakfast each morning of your stay. In addition to free wireless high-speed Internet access each spacious guest room includes a microwave refrigerator 32 flat-screen TV with premium and popular cable channels coffee maker hair dryer iron wironing board free local calls and more. Enjoy a 24-hour business center well-equipped fitness center and much more at the La Quinta Inn and Suites EdgewoodAPG South. La Quinta Returns members are welcomed with express check-in. For more information about the La Quinta Inn and Suites Edgewood Aberdeen-South hotel or to book group reservations at this hotel please email lq6205dosatlaquinta.com.
Show More
4.0/5
Very Good99 review
Price per night from:IDR 998,665
Red Roof Inn Edgewood Hotels in Edgewood

Red Roof Inn Edgewood

Hotel in Edgewood
Red Roof Inn Edgewood is a pet-friendly, family-friendly hotel and is conveniently located off I-95. This location offers free Wi-Fi and free continental breakfast. Nearby attractions include Edgewood Arsenal, Cedar Lane Regional Park and Mountain Branch Golf Course. When you check in, check out the room amenities Red Roof Inn Edgewood has to offer during your stay. The rooms at this newly-hairdryers and in-room coffee makers. The hotel features free Wi-Fi, dining delivery service, coin laundry and wake-up calls. Complimentary coffeehouse-style coffee and tea are offered in the lobby and one well-behaved pet per room is welcome.
Show More
3.5/5
75 review
Price per night from:IDR 1,094,306
Grasonville Hotels in Chestertown

Grasonville

31.4km from Chestertown
Learn More
Best Western Kent Narrows Inn Hotels in Grasonville

Best Western Kent Narrows Inn

Hotel in Grasonville
Enjoy the comforts of home and a great location in the Kent Narrows area. The Best Western Kent Narrows inn is located near the Chesapeake Bay and within walking distance to many local seafood restaurants and dock bars. Inside this Grasonville-area hotel, guests will find each guest room comes complete with HD satellite television (HBO® and Cinemax) and free fiber optic high-speed wireless Internet access. Other amenities at this Kent Narrows hotel also include a free breakfast each morning featuring a deluxe continental breakfast, a relaxing indoor swimming pool and hot tub, on-site exercise facility and guest laundry. Staying on business? The Best Western Kent Narrows Inn offers business services, meeting facilities for up to 50 guests, and a great location near many of the local business parks. Outside this Grasonville hotel, guests will find the best of the area. Play a round at one of our local golf courses. No matter what youre interested in while visiting, our friendly staff can help you plan the perfect Eastern Shore getaway including hunting and fishing. While in town, dont miss out on annual events, like the Bay Bridge Boat Show and the Chesapeake Bay Wine Festival held at the Bay Bridge Marina, the Maryland Seafood Festival and the Polar Bear Plunge held at Sandy Point State Park. Here for a wedding? The Best Western Kent Narrows Inn offers an amazing location near popular wedding venues, like Chesapeake Bay Beach Club, Silver Swan Bayside, Queenstown Harbor, Kent Manor Inn, Prospect Bay Country Club, Marias Love Point Bed Breakfast and Kent Island Yacht Club. Whether traveling for business, leisure, adventure or romance, the Best Western Kent Narrows Inn is the ideal place to stay while in the Grasonville and Chesapeake Bay area. Book today to save! Enjoy your stay.
Show More
3.9/5
101 review
Price per night from:IDR 1,570,285
Hilton Garden Inn Kent Island Marina Hotels in Grasonville

Hilton Garden Inn Kent Island Marina

Hotel in Grasonville
Hilton Garden Inn Kent Island is conveniently located on Maryland's Eastern Shore just minutes from Historic Annapolis and the Chesapeake Bay Bridge. The hotel offers complimentary internet in guest rooms and public spaces. Our amenities include free self-parking, a business center, an indoor heated pool, a fitness center, a Pavilion Pantry mini-mart, and an on-site restaurant and bar open for breakfast and dinner. We provide on-site catering services and have a 1,508 square feet divisible meeting space with a view of the marina. Also available is a 1,000 square feet terrace with a breathtaking view of the bay which is perfect for cocktail parties, and a 273 square feet boardroom for smaller meetings. The hotel is conveniently located by Wells Cove Marina, on Maryland's Eastern Shore just minutes from Historic Annapolis and the Chesapeake Bay Bridge. Some of the area's finest seafood restaurants and dock bars are just steps away. We are nearby golf courses, Cross Island Fitness Trail, Queenstown Premium Outlets, wineries, breweries, beaches, and a nature preserve.
Show More
4.4/5
Excellent98 review
Price per night from:IDR 1,877,224
Quality Inn Hotels in Grasonville

Quality Inn

Hotel in Grasonville
Located in Grasonville, Quality Inn is a 5-minute drive from Chesapeake Exploration Center and 6 minutes from Queenstown Premium Outlets. This hotel is 2.6 mi (4.2 km) from Chesapeake Bay Environmental Center and 3.9 mi (6.3 km) from Queenstown Harbor Golf Links. Take advantage of recreation opportunities such as a seasonal outdoor pool, or other amenities including complimentary wireless internet access and a vending machine. A complimentary buffet breakfast is included. Featured amenities include a computer station, a 24-hour front desk, and a safe deposit box at the front desk. Free self parking is available onsite. Make yourself at home in one of the 59 air-conditioned rooms featuring refrigerators and microwaves. 42-inch flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms have shower/tub combinations and hair dryers. Conveniences include safes and coffee/tea makers, as well as phones with free local calls.
Show More
3.8/5
96 review
Price per night from:IDR 1,423,488
Belcamp Hotels in Chestertown

Belcamp

32.0km from Chestertown
Learn More
TownePlace Suites Edgewood Aberdeen Hotels in Belcamp

TownePlace Suites Edgewood Aberdeen

Hotel in Belcamp
TownePlace Suites by Marriott Edgewood Aberdeen is the newest extended-stay hotel near Ripken Stadium and the Aberdeen Proving Grounds. Stay with us and you can balance work and life as you like. Here at the TownePlace Suites Edgewood Aberdeen we make comfort, flexibility and meet the affordability you require. Relax and feel at home with a fully equipped kitchen and high-speed Internet access. With our home away from home feel, come get away and stay in one of our 96 guestrooms, featuring kitchens with full-sized refrigerators/freezers and stovetops. Wireless Internet access is complimentary, with our 43-inch televisions. Our new digital entertainment options such as YouTube and Netflix alongside with satellite programming provide even more entertainment. Say hello your local favorites as all rooms are equip with phones for complimentary use for local calls and call long distance for a fee.
Show More
4.2/5
Very Good30 review
Price per night from:IDR 2,046,263
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD Hotels in Belcamp

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Hotel in Belcamp
A stay at Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD places you in the heart of Bel Air, a 4-minute drive from Cedar Lane Regional Park and 9 minutes from Cal Ripken Museum. This eco-certified hotel is 6.1 mi (9.8 km) from Ripken Stadium and 6.8 mi (10.9 km) from Harford Community College. Don't miss out on recreational opportunities including a fitness center and a seasonal outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, a fireplace in the lobby, and a banquet hall. At Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD, enjoy a satisfying meal at the restaurant. A complimentary buffet breakfast is served on weekdays from 6:00 AM to 9:30 AM and on weekends from 7:00 AM to 10:30 AM. Featured amenities include complimentary wired internet access, a 24-hour business center, and complimentary newspapers in the lobby. Planning an event in Bel Air? This hotel has 850 square feet (79 square meters) of space consisting of a conference center and a meeting room. Free self parking is available onsite. Make yourself at home in one of the 81 guestrooms featuring refrigerators and LCD televisions. Your pillowtop bed comes with down comforters and premium bedding. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers.
Show More
4.3/5
Excellent97 review
Price per night from:IDR 1,423,488
Holiday Inn Belcamp - Aberdeen Area Hotels in Belcamp

Holiday Inn Belcamp - Aberdeen Area

Hotel in Belcamp
Welcome to the Holiday Inn Belcamp - Aberdeen Area, where we specialize in exceptional hospitality and guest satisfaction, making us the perfect destination for your next stay.Located just minutes from the Aberdeen Proving Ground's 715 Visitors Gate and close to Ripken Stadium, our hotel is designed to provide the ideal setting for business travelers, social gatherings, family reunions, and romantic getaways. Whether you're here for a corporate event, wedding, or simply a relaxing retreat, our modern, spacious accommodations cater to all your needs—without the luxury price tag.Nestled in the heart of Harford County, our hotel offers easy access to local attractions, dining, and shopping. We pride ourselves on delivering a seamless and enjoyable experience for every guest, ensuring that your stay with us is nothing short of exceptional. Be sure to ask our friendly front desk staff for information on local events to make the most of your visit. We’re committed to making every moment of your stay memorable!
Show More
4.1/5
Very Good99 review
Price per night from:IDR 998,665
Aberdeen Hotels in Chestertown

Aberdeen

33.5km from Chestertown
Learn More
Courtyard Aberdeen at Ripken Stadium Hotels in Aberdeen

Courtyard Aberdeen at Ripken Stadium

Hotel in Aberdeen
A one-of-a-kind hotel in a one-of-a-kind location, the Courtyard Aberdeen is designed as a replica of Oriole Park at Camden Yards, directly across from Ripken Stadium and close to I-95. Our spacious Aberdeen MD hotel rooms and suites are ideal for business and leisure, with free WiFi, flexible workspaces, and 40” HDTVs with premium cable. As one of the top hotels in Aberdeen, MD and connected to the Residence Inn Aberdeen, we offer amenities including two restaurants (one with outdoor seating), Lounge, an indoor pool, 24-hour business & fitness center, 24 hr Market and access to outdoor walking paths around the baseball fields. Plan a business meeting or social event in our 1,200 sf of space, and book a group block at our hotel in Bel Air, MD. In addition to Aberdeen Proving Ground, Susquehanna State Park and Bulle Rock Golf Course, we are also convenient to local businesses and major Distribution Centers, including Pepsi-Frito Lay, Wayfair, Webstaurant Store, Amazon and Clorox.
Show More
4.1/5
Very Good27 review
Price per night from:IDR 1,532,473
La Quinta Inn & Suites by Wyndham Aberdeen-Apg Hotels in Aberdeen

La Quinta Inn & Suites by Wyndham Aberdeen-Apg

Hotel in Aberdeen
The newly built La Quinta Inn and Suites Aberdeen-APG is conveniently located off I-95 and the Aberdeen Throughway. Next to the Beards Hill Plaza Shopping Center there are ample shops and restaurants like Chick-fil-A Panera Bread and the popular Chaps Pit Beef within walking distance.While staying at this beautiful hotel guests enjoy FREE WiFi seasonal outdoor pool free parking and the hearty and healthy FREE hot Bright Side Breakfast.Your furry friends are welcome at this location and you all appreciate a 100-percent nonsmoking environment.La Quinta Inn and Suites Aberdeen-APG offers guests an enhanced experience ideal for the modern traveler.With expanded amenities and an innovative design its easy to see the appeal. Situated 40 miles from BWI Airport and 60 miles from Philadelphia International Airport you are also near many businesses and attractions. Spacious rooms and incredible common areas feature eye-catching art ample seating and numerous ways to relax. Plus there are plenty of amenities at your disposal. Guests of the hotel can take a dip in the sparkling outdoor pool between Memorial Day and Labor Day. If you are in need of a workout try the state-of-the-art fitness center stocked with your favorite equipment that includes a treadmill elliptical recumbent bike training bench weights and stability ball. The Bright Side Market offers travel necessities and snacks around the clock and the FREE hot Bright Side Breakfast which has waffles cereal fresh fruit eggs baked goods coffee and juice is served daily. A 24-hour business center is great for corporate guests looking to print copy or fax while a 625-square-foot meeting space with AV equipment is available for groups or events. Wake up in style in one of the rooms or suites. Each features the comfortable Simmons Beautyrest Chadfield recharge pillowtop mattress and a flat-screen TV. An efficient work desk lets you setup your laptop to connect with friends and family and rooms are also outfitted with
Show More
4.4/5
Excellent101 review
Price per night from:IDR 1,258,897
Red Roof Inn Aberdeen Hotels in Aberdeen

Red Roof Inn Aberdeen

Hotel in Aberdeen
Red Roof Inn Aberdeen has rooms that are 100% Smoke-Free. This Red Roof Inn is a great location for business and leisure travelers! Aberdeen Proving Grounds, Army Research Lab, Cal Ripken Museum, Beech Tree and Bulle Rock golf clubs are all within 5 minutes. Harve de Grace Decoy Museum and Harford Community College are only 5 miles away from this hotel. For those visiting Baltimore, Inner Harbor and Oriole Park at Camden Yards are only 30 miles. And we are 10 miles from Hollywood Casino. Conveniently located near I-95, Red Roof Aberdeen is just seconds from restaurants and shopping. We welcome all Government and Military travelers with discounted rates for business and leisure. When you check in, check out the amenities in our rooms! The rooms at this 100% Smoke-Free inn feature a large flat screen TV and free WiFi. Red Roof Aberdeen is offering a new Order Inn program, where guests can order delicious food for in-room delivery. Selected rooms offer microwave/microfridge units. All rooms offer “On Command Video” with a selection of free TV channels, pay-to-view premium channels, movies, music and games. One well-behaved family pet per room is welcome.
Show More
3.1/5
98 review
Price per night from:IDR 838,523

Top hotel picks in Chestertown

See all
Check out these top-booked hotels from the past 30 days!
No.1
Red Roof Inn & Suites Chestertown Hotels in Chestertown
3.6/5
97 review

Red Roof Inn & Suites Chestertown

Hotel near Chestertown
"Good Location"
Select dates to view prices
No.2
Holiday Inn Express Hotel & Suites Chestertown Hotels in Chestertown
4.1/5
97 review

Holiday Inn Express Hotel & Suites Chestertown

Hotel near Chestertown
"Good Location"
Select dates to view prices
No.3
Comfort Inn & Suites Chestertown Hotels in Chestertown
4.1/5
97 review

Comfort Inn & Suites Chestertown

Hotel near Chestertown
"Good Location"
Select dates to view prices
No.4
Driftwood Inn Hotels in Chestertown
2.5/5
20 review

Driftwood Inn

Hotel near Chestertown
"Good Location"
Select dates to view prices

FAQs About Hotels in Chestertown

How do I book a hotel on Trip.com?

To book a hotel on Trip.com, simply enter your destination, travel dates, and the number of guests on the page. Then, browse through the available hotels and select the one you want to book. Follow the prompts to enter your payment information and complete the booking.

How do I get hotel deals on Trip.com?

There are several ways to find affordable hotels on Trip.com. You can narrow down your search results by filtering hotels according to your preferred price range, or you can sort the results by price to view the cheapest options first.

Where can I find hotel deals on Trip.com?

Trip.com offers a wide variety of hotel deals and promotions that are available throughout the year. You can easily find these special offers on our deals page. What's more, if you are a member of our loyalty program, you can sign in to your account and discover exclusive discounted rates at hotel list pages.

How can I get lower prices for hotels?

Sometimes booking hotels midweek is cheaper, but it also depends on the season.

How many hotels are listed on Trip.com?

You can find over 5 million hotels in more than 230 countries or regions on Trip.com. Haven't decided which hotel to book? Browse our site to get ideas!

Can I cancel or change my hotel bookings on Trip.com?

It depends on the hotel policy and date of cancellation. Please check the policy section of the related hotel pages. To cancel or change your bookings, sign in to your Trip.com account, go to "My Bookings", and follow the instructions.

How do I contact Trip.com customer support?

You can contact Trip.com's 24/7 customer support by visiting the Help Center on Trip.com and submitting a request. You can also contact us by phone or service chat, depending on your location.

Local Travel Info

Highest PriceIDR 5,881,628
Lowest PriceIDR 1,042,838
Number of Reviews390
Total Properties14
Average Price (Weekdays)IDR 1,714,190
Average Price (Weekends)IDR 2,037,611