Find hotels in Chestertown, MD from $57

Top reasons to visit Chestertown

• Historic Charm: Stroll through the charming streets of Chestertown, rich in history and featuring beautiful architecture.
• Outdoor Adventures: Enjoy a variety of outdoor activities in scenic parks and along the picturesque waterfront.
• Family-Friendly Atmosphere: Chestertown offers numerous family-oriented attractions and activities for all ages.
• Relaxing Environment: Experience a peaceful getaway with low crowds and a tranquil atmosphere perfect for relaxation.
• Diverse Accommodations: Choose from a range of hotels catering to various needs, ensuring a comfortable stay.

Find great hotels near Chestertown

Discover the charm of Chestertown, Maryland, with a range of hotel accommodations designed to meet the needs of every traveler. Whether you're seeking pet-friendly options, business-themed amenities, or a welcoming atmosphere for LGBTQIA guests, you'll find the perfect place to unwind. Explore top-rated hotels and suites, complete with essential services and positive reviews, ensuring a memorable visit to this picturesque waterfront town.

• Quality Inn & Suites Bel Air I-95 Exit 77A: This hotel is designed for business travelers seeking a practical and efficient stay. Located 21 miles away from Chestertown, it features a range of amenities tailored for the professional guest, including high-speed internet access, a well-equipped business center, and meeting rooms. Guests appreciate the spacious rooms that offer comfortable workspaces, as well as a complimentary breakfast to kickstart their day. Ideal for those on the go, this property ensures a productive yet relaxing experience.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: Perfect for pet owners, this hotel welcomes furry friends with open arms. Situated 21 miles from Chestertown, it offers a host of pet-friendly amenities, ensuring your four-legged family members enjoy their stay as much as you do. Guests rave about the spacious rooms, complimentary breakfast, and the hotel's convenient location near shopping and dining options. With a focus on comfort and warmth, La Quinta is a great choice for travelers who want to bring their pets along.
• Red Roof Inn Aberdeen: This hotel not only embraces pets but also proudly supports the LGBTQIA community, making it an inclusive choice for all travelers. Located 22 miles from Chestertown, Red Roof Inn Aberdeen features a welcoming atmosphere with various pet amenities, including variable fees for pet stays and a strict pet policy. Guests appreciate the modern accommodations, affordability, and commitment to diversity. With a focus on comfort and community, this hotel is an excellent option for those looking to travel with their pets in a welcoming environment.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of history and outdoor adventure, making it a perfect getaway. Discover the charming streets of historic Chestertown, where family-friendly activities abound. The Eastern Shore's picturesque scenery invites relaxation, while low crowds allow for a peaceful exploration of local attractions. Enjoy the friendly atmosphere and budget-friendly options as you create memorable experiences in this welcoming town and its surrounding regions.

• Worton: Located approximately 4 miles from Chestertown, Worton is a charming city that attracts visitors year-round, particularly during the spring and summer months. Travelers flock to Worton for its stunning outdoor scenery and recreational opportunities. Popular activities include exploring the nearby national state park, enjoying a day at the beach, or visiting the local marina. Whether you’re hiking, picnicking, or simply soaking in the natural beauty, Worton offers a refreshing escape for outdoor enthusiasts.
• Georgetown: Nestled within the Chestertown area, Georgetown is a delightful village known for its romantic ambiance and adventurous spirit. The peak travel season occurs from June to August, when visitors can engage in various outdoor activities and explore the local recreation centers. Georgetown is home to several notable landmarks, including a sports facility and a national state park, making it an ideal spot for both relaxation and adventure. Whether you’re looking to hike, play sports, or simply enjoy a peaceful day outdoors, Georgetown has something for everyone.
• Tolchester Beach: Situated close to Chestertown, Tolchester Beach is a picturesque village that draws visitors year-round, with peak numbers in the summer months. Known for its beautiful beaches and scenic views, Tolchester Beach is perfect for travelers seeking outdoor fun and relaxation. Enjoy leisurely strolls along the boardwalk, engage in various recreational activities, or spend a day soaking up the sun at the beach. With access to nearby marinas and a national state park, Tolchester Beach is a fantastic spot for those looking to unwind and connect with nature.

Things to do in and around Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor activities and scenic beauty, perfect for a relaxing vacation. Visitors can enjoy educational experiences, explore recreational areas, and stroll along the charming boardwalk. The town's picturesque surroundings and tranquil atmosphere make it an ideal destination for those seeking both adventure and leisure.

Shopping

In Chestertown, you can enjoy local shops and boutiques for unique gifts and souvenirs. If you're up for a drive, visit Queenstown Premium Outlets, 17 miles away, for a variety of stores, or explore Westown, 24 miles away, for more shopping options and a vibrant atmosphere.

Recreation

Experience the vibrant atmosphere at Ripken Stadium, where you can catch a game and enjoy the excitement of local sports. For a more tranquil outing, visit Queenstown Harbor Golf Club or Queenstown Harbor Golf Links, both offering beautiful outdoor settings for a relaxing day of golf.

Adventure

At Annapolis Sailing School, located 28 miles from Chestertown, you can experience the thrill of sailing on the Chesapeake Bay. Emmorton Recreation & Tennis Center, 24 miles away, offers exciting tennis matches and outdoor activities. Tose Family Tennis Center, also 28 miles from Chestertown, is perfect for tennis enthusiasts seeking adventure.

Nightlife

In Chestertown, the Garfield Center for the Arts at the Prince Theater offers captivating performances in a charming atmosphere. A short drive away, the Church Hill Theatre provides delightful shows, while the Avalon Theatre, just 31 miles away, presents a variety of cultural entertainment options for a memorable night out.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, visit during the off-peak months of January to February and November, when accommodation prices drop. Consider booking your stay for a Tuesday, the least expensive day, and utilize Expedia's search tool to find budget-friendly hotels, including eco-certified options. Look for package deals to combine flights, hotels, and activities for additional savings. Joining Expedia's One Key membership can provide exclusive discounts and earn you OneKeyCash for future bookings, ensuring you get the best rates during your visit.

• 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: Expedia's search tool offers you the flexibility to choose your budget, desired location, and additional preferences. You can arrange your results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you have the option to filter your search by hotel type. For instance, by selecting the Eco-certified filter, you'll be able to view a range of sustainable and environmentally friendly hotels that are available for booking.
• Consider bundling your trip: You can save money by combining your hotel stay in Chestertown with your flights and activities through an Expedia package deal.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in Chestertown

Chestertown, Maryland, offers a delightful vacation experience for outdoor enthusiasts and families alike. With its beautiful parks, marinas, and picturesque scenery, visitors can enjoy a variety of activities that highlight the area's natural beauty. Whether you're seeking a relaxing beach day or an adventurous outing, Chestertown's attractions cater to all types of travelers looking to explore this charming town.

• Washington College: Experience the charm of this historic institution, founded in 1782, nestled in the heart of Chestertown. Explore its beautiful campus, rich with cultural events, art exhibitions, and a dynamic student life that reflects the vibrant spirit of education and community.
• Rolphs Wharf Marina: Embrace the great outdoors at Rolphs Wharf Marina, where adventure awaits. Enjoy activities like kayaking and fishing, or simply relax by the water's edge while soaking in the sun and beach vibes that this scenic marina offers.
• Historical Society of Kent County Maryland: Delve into the local history at this engaging museum, showcasing artifacts and exhibits that tell the story of Kent County's past. It's a perfect spot for history buffs and anyone interested in understanding the area's cultural heritage.

Best time to go to Chestertown

The best time to visit Chestertown is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	34.2°F (1.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	43.7°F (6.5°C)	Light Rain	Mostly Sunny	Average	Average
April	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	63.7°F (17.6°C)	Light Rain	Mostly Sunny	Average	Average
June	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	77.4°F (25.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	75.6°F (24.2°C)	Light Rain	Mostly Sunny	Average	Average
September	69.4°F (20.8°C)	Light Rain	Mostly Sunny	Average	Average
October	59.2°F (15.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	47.3°F (8.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
December	40.1°F (4.5°C)	Light Rain	Mostly Sunny	Slightly Low	Average

The nearest major airports for your trip to Chestertown

To visit Chestertown, Maryland, you have several airport options. Washington, DC (DCA-Ronald Reagan Washington National) is 58 miles away, with luxury accommodations like the InterContinental Washington D.C. - The Wharf, Riggs Washington DC, and Salamander Washington DC, all within a short distance from the airport. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is closer at 32 miles, featuring high-end hotels such as Sagamore Pendry Baltimore, Four Seasons Hotel Baltimore, and The Ivy Hotel. For a smaller option, Baltimore, MD (MTN-Martin State) is 20 miles away, with hotels like Canopy by Hilton Baltimore Harbor Point and Hyatt Place Baltimore Inner Harbor nearby.