Photo by Patricia Knorr

Search Chestertown hotels

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (828)
"Great service. Very clean."
The price is AU$174
includes taxes & fees
19 Oct - 20 Oct
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (404)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is AU$138
includes taxes & fees
23 Oct - 24 Oct
Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing
3.5 star property
7.8 out of 10, Good, (70)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
The price is AU$232
includes taxes & fees
19 Oct - 20 Oct
The Lodge at Great Oak Landing
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
3.0 star property
7.0 out of 10, Good, (1021)
"Had a nice stay "
The price is AU$133
includes taxes & fees
26 Oct - 27 Oct
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
9.2 out of 10, Wonderful, (906)
"Nice Holiday Inn Express with great water views."
The price is AU$209
includes taxes & fees
30 Oct - 31 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
Country Inn & Suites by Radisson, Baltimore North, MD
3.0 star property
7.2 out of 10, Good, (1007)
"I have been staying here for some time now and I've always been happy and every time I come in they always remember me very welcoming very helpful above and beyond service and always ask how the families doing how I'm doing it's like being home when you're away from home very happy with the place very clean rooms very nice affordable prices and staff does an amazing job working hard on keeping the place clean amazing breakfast rooms are always clean the whole place and the staff and give it a 10...
The price is AU$162
includes taxes & fees
26 Oct - 27 Oct
Country Inn & Suites by Radisson, Baltimore North, MD
Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
7.2 out of 10, Good, (1018)
"Great hotel "
The price is AU$107
includes taxes & fees
2 Nov - 3 Nov
Quality Inn & Suites Bel Air I-95 Exit 77A
Best Western Plus Hotel & Conference Center
2.5 star property
7.8 out of 10, Good, (1000)
"Great stay"
The price is AU$193
includes taxes & fees
2 Nov - 3 Nov
Best Western Plus Hotel & Conference Center
Comfort Inn & Suites Aberdeen near APG
2.5 star property
7.8 out of 10, Good, (778)
"Room was clean, price is very reasonable. "
The price is AU$152
includes taxes & fees
19 Oct - 20 Oct
Comfort Inn & Suites Aberdeen near APG
Fairfield Inn & Suites by Marriott White Marsh
2.5 star property
8.6 out of 10, Excellent, (1010)
"Convenient access from I-95, several dining options in close proximity"
The price is AU$172
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott White Marsh
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (638)
"Great location and rooms. Great place!"
The price is AU$245
includes taxes & fees
21 Oct - 22 Oct
Hyatt Place Kent Narrows & Marina
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is AU$338
includes taxes & fees
15 Oct - 16 Oct
Kent Island Resort
Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
9.4 out of 10, Exceptional, (1005)
"Love love love this hotel they provided me with excellent care. Also helped me out with late checkout as needed. Great stay booking again very soon "
The price is AU$144
includes taxes & fees
11 Nov - 12 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
Americas Best Value Inn Edgewood
2.0 star property
5.6 out of 10, (989)
"Stayed 3 nights. The beds were comfortable, the rooms were clean. "
The price is AU$98
includes taxes & fees
28 Oct - 29 Oct
Americas Best Value Inn Edgewood
Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
9.0 out of 10, Wonderful, (583)
"This Hotel was excellent in all ways. "
The price is AU$168
includes taxes & fees
30 Oct - 31 Oct
Hampton Inn & Suites Baltimore/Aberdeen
Super 8 by Wyndham Aberdeen MD
2.0 star property
7.0 out of 10, Good, (851)
"Parking was easy. Bed was super comfy. "
The price is AU$108
includes taxes & fees
10 Nov - 11 Nov
Super 8 by Wyndham Aberdeen MD
Hampton Inn Baltimore Bayview Campus
3.5 star property
9.0 out of 10, Wonderful, (1007)
"We’ve stayed here two times already and always enjoyed it! Clean rooms, friendly staff, free parking and many shopping options close by!"
The price is AU$235
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn Baltimore Bayview Campus
Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
5.4 out of 10, (396)
"Just a nice quiet cool place clean rooms and the bed is away from the door lol"
The price is AU$172
includes taxes & fees
26 Oct - 27 Oct
Super 8 by Wyndham Baltimore/Essex Area
Hilton Garden Inn Kent Island Marina
3.0 star property
9.0 out of 10, Wonderful, (1003)
"Hotel was great, beautiful location near the water"
The price is AU$250
includes taxes & fees
19 Oct - 20 Oct
Hilton Garden Inn Kent Island Marina
Hampton Inn Baltimore/White Marsh
2.5 star property
7.8 out of 10, Good, (1008)
"Really enjoyed my stay, the staff were nice."
The price is AU$176
includes taxes & fees
21 Oct - 22 Oct
Hampton Inn Baltimore/White Marsh
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Chestertown attractions

Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

More cheap accommodation in Chestertown

Find out more about Chestertown

Top reasons to visit Chestertown

  • Historic Downtown: Stroll through cobblestone streets lined with quaint shops and enjoy the rich history of this charming town.
  • Scenic Beauty: Chestertown boasts picturesque views and outdoor activities, perfect for nature lovers and families alike.
  • Vibrant Atmosphere: High Street offers a lively atmosphere with local events and performances, ideal for budget travellers.
  • Relaxing Boardwalk: Unwind at the scenic boardwalk, perfect for leisurely walks and enjoying the tranquil waters.
  • Diverse Accommodation: Find a range of welcoming lodging options, catering to all needs, including pet-friendly and LGBTQIA-friendly stays.

Find great hotels near Chestertown

Explore a range of accommodation options in Chestertown, Maryland, where you'll find welcoming hotels and motels perfect for any traveller. Whether you're seeking pet-friendly amenities, business-focused facilities, or an LGBTQIA-friendly environment, Chestertown has the ideal lodging for your needs. From comfortable suites to charming hotels, your stay in this picturesque town will be both enjoyable and memorable.

  • Quality Inn & Suites Bel Air I-95 Exit 77A: Ideal for the business traveller, Quality Inn & Suites Bel Air I-95 Exit 77A is designed with convenience and productivity in mind. Located 33.8km from Chestertown, this hotel provides excellent amenities such as complimentary Wi-Fi, a business centre, and meeting facilities. Guests can enjoy a hearty breakfast to fuel their day, while comfortable rooms ensure a restful stay after a busy day of meetings. Its strategic location near I-95 allows for easy access to local businesses and attractions.
  • La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: For those who cherish the companionship of their pets while enjoying nature, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A is an excellent choice. Situated 33.8km from Chestertown, this hotel welcomes both dogs and cats, making it a perfect stop for pet owners. Guests can take advantage of nearby parks and natural reserves, while the hotel offers a comfortable stay with amenities like free breakfast and a fitness centre. The welcoming atmosphere is complemented by a pet-friendly policy, ensuring a delightful experience for all.
  • Red Roof Inn Aberdeen: Located 35.4km from Chestertown, Red Roof Inn Aberdeen is not only pet-friendly but also embraces an inclusive atmosphere for LGBTQIA travellers. This hotel offers a comfortable and welcoming environment, allowing small pets, making it a great choice for those travelling with furry companions. Guests can look forward to amenities such as complimentary Wi-Fi and free coffee in the lobby. Its affiliation with LGBTQI travel guides ensures a friendly and accommodating experience for everyone.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of history and charm, perfect for a summer getaway. Explore the historic downtown, where cobblestone streets and quaint shops await. Discover the vibrant atmosphere along High Street, ideal for families and budget travellers alike. Enjoy the scenic beauty of the area, with opportunities for outdoor activities and relaxation. Whether you’re wandering through historic Chestertown or soaking up the friendly vibes, this destination promises an unforgettable experience.

  • Worton: Located a mere 6.4km from Chestertown, Worton provides a delightful escape for outdoor enthusiasts. This charming city offers a moderately seasonal travel experience, peaking in April to May and July, making it ideal for those seeking beachside adventures and stunning scenery. Visitors can explore nearby beaches, marinas, and the expansive national state park, perfect for hiking and picnicking. Worton's recreational areas and educational venues make it a great spot for families and nature lovers alike.
  • Georgetown: Nestled within the Chestertown area, the quaint village of Georgetown is known for its romantic charm and adventurous spirit. With peak travel from June to August, this village caters to those looking for outdoor activities and recreational opportunities. Visitors can engage in various sports at the local stadium and enjoy the national state park's beauty, making it perfect for couples and families. The area's scenic landscapes provide fantastic backdrops for memorable experiences.
  • Tolchester Beach: A picturesque village close to Chestertown, Tolchester Beach is a hidden gem for beach lovers and outdoor adventurers alike. While it experiences a more consistent flow of visitors, it peaks in May and the summer months. The inviting boardwalk and recreational areas offer plenty of opportunities for relaxation and fun. With stunning beaches and a nearby marina, Tolchester Beach is an ideal spot for sunbathing, swimming, and enjoying the natural surroundings.

Things to do in and around Chestertown

Chestertown offers a delightful getaway with its scenic beauty and outdoor activities. Visitors can explore educational attractions, enjoy live music performances, and relax at the picturesque boardwalk. For those keen on camping, there are several campgrounds available. Whether you're after recreational areas or simply soaking in the local charm, Chestertown promises a memorable experience for all.

Shopping

In Chestertown, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, check out Queenstown Premium Outlets, 27.4km away, for a variety of brands. For more options, consider Westown, located 38.6km from Chestertown, offering a lovely mix of shops.

Recreation

Ripken Stadium, 35.4km from Chestertown, offers an energetic atmosphere with thrilling sports events. For golf enthusiasts, Queenstown Harbor Golf Club and Queenstown Harbor Golf Links, both 27.4km away, provide stunning outdoor settings, perfect for a relaxing day on the greens amidst beautiful landscapes.

Adventure

Emmorton Recreation & Tennis Center, located 38.6km from Chestertown, offers vibrant adventure vibes with various sporting activities. For water enthusiasts, Annapolis Sailing School, 45.1km away, provides thrilling sailing experiences amidst beautiful waters. Tose Family Tennis Center, also 45.1km from Chestertown, boasts exciting tennis activities in a lively atmosphere.

Nightlife

For a vibrant night in Chestertown, catch a show at the Garfield Center for the Arts, offering a mix of entertainment and culture. Alternatively, the Avalon Theatre and Milburn Stone Theater, both nearby, promise delightful performances in a charming setting, perfect for a romantic evening out.

Booking tips and Expedia advantages for Chestertown

When visiting Chestertown, Maryland, the best time to save money is during the off-peak months of January, February, and November, with Tuesdays being the cheapest days for accommodation. Avoid the pricier months of June, July, and October, and consider using Expedia to find budget-friendly lodging by filtering for eco-certified hotels. Look for package deals that combine flights, hotels, and activities for additional savings. Don't forget to explore free local attractions and use public transport for economical travel around the charming town.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chestertown are January to February and November, where the prices are slightly lower. This is in comparison to June to July and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chestertown is Tuesday. The most expensive day to stay in Chestertown is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your options based on your budget, desired location, and preferred hotel style. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels currently available. To find the most affordable prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially save money by combining your Chestertown hotel booking with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chestertown

Chestertown offers a delightful blend of outdoor activities and scenic beauty, making it perfect for a family getaway. You can explore local beaches, parks, and urban parks, all designed for those seeking a refreshing beach experience. Whether you're enjoying the tranquil waters or wandering through lush green spaces, Chestertown has plenty to keep you entertained during your visit.

  • Eastern Neck National Wildlife Refuge: Located 25.7km from Chestertown, this beautiful reserve offers a family-friendly atmosphere where you can explore diverse wildlife and scenic landscapes. Perfect for nature walks, birdwatching, and picnics, it’s a great spot to unwind and connect with nature.
  • Washington College: Nestled in the heart of Chestertown, this historic college boasts stunning architecture and a lively cultural scene. Visitors can enjoy art exhibitions, lectures, and campus tours that showcase the college's rich history and academic vibrancy.
  • Rolphs Wharf Marina: Situated within Chestertown, this marina is ideal for adventure seekers. Enjoy boating, fishing, and water sports, or simply relax by the beach and soak up the outdoor atmosphere, making it a perfect getaway for thrill-seekers.

Best time to go to Chestertown

The best time to visit Chestertown can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chestertown falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chestertown falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January34.2°F (1.2°C)Light RainMostly SunnySlightly LowSlightly Low
February36.9°F (2.7°C)Light RainMostly SunnyAverageSlightly Low
March43.7°F (6.5°C)Light RainMostly SunnyAverageAverage
April54.3°F (12.4°C)Light RainMostly SunnySlightly HighAverage
May63.7°F (17.6°C)Light RainMostly SunnyAverageAverage
June72.1°F (22.3°C)Light RainMostly SunnySlightly HighSlightly High
July77.4°F (25.2°C)Light RainMostly SunnySlightly HighSlightly High
August75.6°F (24.2°C)Light RainMostly SunnyAverageAverage
September69.4°F (20.8°C)Light RainMostly SunnyAverageAverage
October59.2°F (15.1°C)Light RainMostly SunnyAverageSlightly High
November47.3°F (8.5°C)Light RainMostly SunnySlightly LowSlightly Low
December40.1°F (4.5°C)Light RainMostly SunnySlightly LowAverage

The nearest major airports for your trip to Chestertown

Travelling to Chestertown, Maryland, is convenient with three major airports nearby. Washington, DC (DCA-Ronald Reagan Washington National) is 93.3km away, with luxurious hotels like the Salamander Washington DC and InterContinental Washington D.C. - The Wharf, both located 3.2km from the airport. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is closer at 33.2km, featuring top-notch accommodations such as the Four Seasons Hotel Baltimore and Sagamore Pendry Baltimore, both 12.9km away with comprehensive transport services. Lastly, Baltimore, MD (MTN-Martin State) is 32.2km from Chestertown, offering options like the Canopy by Hilton Baltimore Harbor Point and Hyatt Place Baltimore Inner Harbor, both 16.1km away.

Frequently asked questions

Where is the best place for a stay in Chestertown?
The Lodge at Great Oak Landing is a favourite property for Expedia customers. This lodge offers a golf course and 3 bars. Reviews from our site also recommend Red Roof Inn & Suites Chestertown and Driftwood Inn as top options for your stay. See all available top hotels, or vacation rentals in Chestertown.
What are some of the best holiday rentals that Chestertown has to offer?
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!: This holiday home rental outside of Chestertown is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. See all vacation rentals in Chestertown.
If I need to cancel my hotel reservation in Chestertown, will I receive a refund?
Yes! You'll find that most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.
What's the best family accommodation in Chestertown?
Red Roof Inn & Suites Chestertown is a hotel with free parking and laundry facilities, and it's a top choice on Expedia for families. Comfort Inn & Suites Chestertown is another good option for your stay with the kids. Also, children of all ages will enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.
What is the top LGBTQ-friendly hotel in Chestertown?
Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing are two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Chestertown.
What's the best dog-friendly accommodation option in Chestertown?
Red Roof Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers laundry facilities and free newspapers for its human guests. Other good options for you and your pet include Comfort Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.
What's the best hotel to stay near the beach in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool and 3 bars/lounges, and it's located near a private beach . See more stays near the beach in Chestertown.
What are some accommodation options with pools in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars/lounges and free WiFi. View all hotels with pools in Chestertown.
How is it to stay in Chestertown?
Visitors to Chestertown will definitely enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals and art. In Chestertown, there are 38 hotels and other accommodation options to choose from. Find out more about Chestertown.
What should I see while I'm in Chestertown?
Cultural venues include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. A couple of additional sights to add to your itinerary are Rolphs Wharf Marina and Chestertown Historic District. Take a look at what more there is to see and do in Expedia's Chestertown guide.
What's the seasonal weather like in Chestertown?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.

Explore a world of travel with Expedia