Find hotels in Chestertown, MD from ₩83,801

Top reasons to visit Chestertown

• Charming Historic District: Explore the picturesque streets of Chestertown, filled with historic architecture and local shops.
• Outdoor Adventures: Enjoy scenic parks and natural beauty, perfect for hiking, picnicking, and connecting with nature.
• Vibrant Community Spirit: Experience the warm hospitality of friendly locals who welcome visitors to their town.
• Beautiful Beaches: Relax at nearby beaches along the Eastern Shore, ideal for sunbathing and water activities.
• Diverse Accommodations: Choose from a variety of lodging options, including pet-friendly hotels and budget-friendly stays.

Find great hotels near Chestertown

Chestertown, Maryland, offers a diverse selection of accommodations to suit every traveler’s needs. From welcoming hotels and motels to pet-friendly options, you’ll find the perfect place to unwind. Whether you're on a business trip or seeking an LGBTQIA-friendly getaway, Chestertown's hotels are designed to provide comfort and convenience while allowing you to explore the charm of this historic town.

• Quality Inn & Suites Bel Air I-95 Exit 77A: Located 34km from Chestertown, Quality Inn & Suites Bel Air I-95 Exit 77A offers a budget-friendly lodging experience ideal for business travelers. The hotel features comfortable rooms equipped with essential amenities, including complimentary Wi-Fi, a business center, and meeting facilities. Guests can enjoy a hot breakfast to kick-start their day, making it a practical choice for those needing convenience and functionality during their stay.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: Also situated 34km from Chestertown, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A is a pet-friendly hotel with a guest rating of 8.2 out of 10. This inviting accommodation allows pets, making it suitable for travelers who wish to bring their furry friends along. The hotel offers modern amenities, including a fitness center, free breakfast, and spacious rooms, ensuring a comfortable stay for both you and your pets.
• Americas Best Value Inn Edgewood: Americas Best Value Inn Edgewood, located 34km from Chestertown, is another budget-friendly option catering to pet owners. With a welcoming atmosphere, this hotel offers essential amenities and a convenient location for exploring the area. The pet policy allows for dogs and cats, and guests can enjoy comfortable accommodations along with basic services. It's a solid choice for those traveling with pets who seek affordability and accessibility.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of history and natural beauty, perfect for outdoor enthusiasts and families alike. Explore the charming streets of historic Chestertown, where friendly locals welcome you to experience the vibrant atmosphere. Venture to the serene Eastern Shore for breathtaking scenery and peaceful retreats. Whether you're seeking relaxation or a budget-friendly getaway, Chestertown and its surrounding areas promise memorable adventures for every traveler.

• Worton: Located 6km from Chestertown, Worton is a charming city that offers a delightful blend of outdoor adventures and scenic beauty. Visitors are drawn to its recreational areas where they can enjoy a variety of activities, from hiking to picnicking. The landscape features picturesque beaches, serene bays, and tranquil lakes, making it an ideal spot for nature lovers. Seasonal traveler numbers peak during the spring and summer months, particularly in April to May and July, providing a lively atmosphere for outdoor enthusiasts.
• Georgetown: Nestled close to Chestertown, Georgetown is a quaint village that thrives on its outdoor and romantic offerings. With visitor numbers peaking from June to August, the village becomes a hub for entertainment and recreation. Travelers can explore the local recreation center, hike scenic trails, and enjoy the nearby beach and marina. Georgetown's proximity to a national state park adds to its allure, providing stunning views and a perfect backdrop for a leisurely getaway.
• Tolchester Beach: This inviting village, located near Chestertown, is known for its family-friendly beaches and vibrant atmosphere. With visitor numbers rising in May and the summer months, Tolchester Beach offers a variety of outdoor activities, including skiing and educational experiences. The area features beautiful beaches, well-maintained family beach areas, and a marina, making it perfect for water sports and relaxation. Whether you're soaking up the sun or enjoying the local attractions, Tolchester Beach promises a memorable visit.

Things to do in Chestertown

Shopping

In Chestertown, explore local shops like the RiverArts Gallery for unique art pieces and the Chestertown Farmer's Market for fresh produce and handmade goods. If you're up for a drive, visit the nearby Dover Mall, about 40km away, featuring a mix of national retailers and dining options.

Recreation

The Lavender Fields Spa offers a tranquil atmosphere with soothing treatments, including massages and aromatherapy. For outdoor relaxation, visit the Chestertown Marina, where you can enjoy scenic views, kayaking, and peaceful walks along the waterfront, immersing yourself in nature's beauty.

Adventure

Explore the Chester River by kayak for an exhilarating paddle through scenic waters, spotting wildlife along the way. For a thrilling land adventure, hike the nearby trails at the Eastern Neck National Wildlife Refuge, where you can enjoy beautiful landscapes and diverse ecosystems.

Nightlife

Explore the lively atmosphere at the Chestertown Brewing Company, where you can enjoy locally crafted beers and often catch live music. For a cozy evening, visit The Fish Whistle for waterfront views and a laid-back vibe, perfect for unwinding after a day of sightseeing.

Find the best attractions in and around Chestertown

Chestertown, Maryland, is perfect for outdoor enthusiasts and families seeking beach and scenic experiences. Visitors can explore the charming historic district of Chestertown, while parks and urban spaces offer ample opportunities for relaxation and recreation. Enjoy the local beaches and immerse yourself in the natural beauty of the area, making it an ideal getaway for those looking to connect with nature and history.

• Wilmer Park: Nestled in the heart of Chestertown, Wilmer Park offers a serene outdoor escape with picturesque views of the Chester River. It's an ideal spot for families to enjoy picnics, strolls along the waterfront, and playground fun, all while soaking in the vibrant city atmosphere.
• Ferry Park: Located 19km from Chestertown, Ferry Park presents a charming blend of natural beauty and recreational activities. This urban park is perfect for families looking to explore the outdoors, featuring walking trails, picnic areas, and playgrounds surrounded by lush greenery.
• Historical Society of Kent County Maryland: Situated within Chestertown, this history museum offers a glimpse into the local culture and heritage. Visitors can explore fascinating exhibits that highlight the region's history, making it a meaningful stop for those interested in learning about Kent County's past.

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.

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

Traveling to Chestertown, Maryland, is convenient with several nearby airports. Philadelphia International Airport (PHL) is 101km away, with luxurious hotels like W Philadelphia and The Ritz-Carlton located 6-11km from the airport. Ronald Reagan Washington National Airport (DCA), situated 93km from Chestertown, offers 5-star accommodations such as the InterContinental Washington D.C. - The Wharf and Pendry Washington DC - The Wharf within a couple of miles. Washington Dulles International Airport (IAD) is 122km away, featuring hotels like Hyatt Regency Dulles International Airport and The Westin Washington Dulles Airport, both just 1.6km from the airport. Each airport provides accessible transport options for travelers.