Find hotels in Chestertown, MD from ฿2,092

Top reasons to visit Chestertown

• Scenic Waterfront: Chestertown features a picturesque waterfront, perfect for leisurely strolls and family outings.
• Historic Charm: The town is rich in history, with charming streets and friendly locals that enhance the cultural experience.
• Outdoor Adventures: Visitors can engage in various outdoor activities, from parks to nearby beaches, ideal for nature enthusiasts.
• Budget-Friendly Accommodations: Chestertown offers a range of affordable hotels and motels catering to diverse traveller needs.
• Family-Friendly Atmosphere: The town's welcoming environment makes it an excellent destination for families seeking relaxation and exploration.

Find great hotels near Chestertown

Discover a delightful stay in Chestertown, Maryland, where charming hotels and motels offer a warm welcome to all travellers. Whether you're seeking pet-friendly options, accommodations for business travel, or a LGBTQIA-friendly environment, Chestertown boasts a variety of hotels tailored to meet your needs. Experience the perfect blend of comfort and hospitality during your visit to this picturesque town.

• Quality Inn & Suites Bel Air I-95 Exit 77A: This budget-friendly hotel offers a convenient lodging option for those on business travel. Located 34km from Chestertown, guests appreciate the practical amenities that cater to their professional needs. The hotel features complimentary Wi-Fi, a business centre, and meeting spaces, making it an ideal choice for corporate guests. Comfortable rooms ensure a restful stay, while the proximity to major highways allows for easy access to surrounding areas.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: Renowned for its pet-friendly policies, this budget hotel boasts a guest rating of 8.2 out of 10. Situated 34km from Chestertown, it welcomes both furry companions and their owners. Amenities include free breakfast, spacious rooms, and a fitness centre, catering to a relaxed stay. The hotel's friendly atmosphere and convenience for pet owners make it a delightful choice for travellers seeking comfort and accessibility during their visit.
• Americas Best Value Inn Edgewood: Another excellent budget accommodation, Americas Best Value Inn Edgewood is also located 34km from Chestertown. This hotel permits pets and provides a welcoming environment for animal lovers. With essential amenities such as free Wi-Fi and comfortable lodging, guests can enjoy a pleasant stay. The hotel’s pet policy includes flexible options, making it accommodating for those travelling with pets while ensuring a comfortable experience for all guests.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor adventures and historical charm. Nestled on the Eastern Shore, this peaceful location invites travellers to explore its scenic waterfront and family-friendly atmosphere. Wander through the historic streets of Chestertown, where friendly locals and budget-friendly options abound. Whether you seek relaxation or a taste of local history, Chestertown presents a unique experience that caters to all types of holidaymakers.

• Worton: Situated a mere 6km from Chestertown, Worton is a charming city that offers a delightful escape into nature. Visitors are drawn to its scenic landscapes, where outdoor enthusiasts can enjoy various recreational activities. The travel experience here is best enjoyed in the spring and summer months, particularly from April to May and July, when the area's beauty is at its peak. With proximity to beaches, bays, and lakes, Worton is perfect for those seeking tranquillity and picturesque views. The local landmarks provide ample opportunities for exploration and relaxation amidst the great outdoors.
• Georgetown: Nestled close to Chestertown, Georgetown is a quaint village that thrives on its outdoor charm and romantic ambience. The village sees a rise in traveller numbers from June to August, making it an ideal summer getaway. Georgetown offers a variety of attractions, including hiking trails and recreational centres, perfect for those looking to engage in outdoor activities. Visitors can also explore nearby beaches and a marina, enhancing the village's appeal. With its enchanting atmosphere and engaging entertainment options, Georgetown is a fantastic destination for couples and families alike.
• Tolchester Beach: A peaceful village located near Chestertown, Tolchester Beach invites visitors to unwind and revel in its outdoor beauty year-round. While the peak travel times occur in May and during the summer months of July to August, the village remains a delightful retreat throughout the seasons. Known for its inviting beaches and family-friendly atmosphere, Tolchester Beach also boasts a marina and educational opportunities for those keen on learning while enjoying their holiday. Whether you're sunbathing on the shore or exploring local attractions, this village promises a memorable seaside experience.

Things to do in Chestertown

Shopping

In Chestertown, the local shops offer unique gifts and souvenirs, particularly along High Street. If you're up for a drive, visit the nearby Chesterfield Towne Center, where you'll find a variety of retail stores and dining options to enhance your shopping experience.

Recreation

The Well Retreat in Chestertown offers a tranquil environment for yoga and meditation, surrounded by nature. Enjoy personalised wellness programmes that incorporate mindfulness practices and holistic therapies. For outdoor enthusiasts, the nearby Chester River provides opportunities for kayaking and peaceful riverside walks.

Adventure

Explore the scenic Chester River by kayaking or paddleboarding, where you can enjoy the tranquil waters and spot local wildlife. For a thrilling experience, try cycling along the picturesque trails that wind through the area, offering stunning views of the surrounding landscape.

Nightlife

In Chestertown, The Garfield Center for the Arts hosts engaging live performances and events, while the local pubs offer a relaxed atmosphere with craft beers and live music. The waterfront along the Chester River provides a scenic backdrop for evening strolls and casual dining experiences.

Find the best attractions in Chestertown

Chestertown, Maryland, is an ideal destination for those seeking outdoor adventures and scenic beauty. Visitors can enjoy parks, urban parks, and nearby beaches, making it perfect for family outings and beach experiences. A must-visit is the historic Chestertown, where you can immerse yourself in the local culture and history. With so much to explore, Chestertown promises a delightful vacation for every traveller.

• Historical Society of Kent County Maryland: Discover the rich heritage of Kent County at this engaging museum. It offers a glimpse into local history through exhibits that reflect the culture and stories of the area, making it a fascinating stop for history enthusiasts.
• Wilmer Park: Enjoy the serene beauty of this urban park, perfect for families and outdoor activities. With its scenic views and well-maintained paths, it's ideal for leisurely strolls, picnics, or simply basking in nature amidst the city landscape.
• River Arts Chestertown: Immerse yourself in the local arts scene at this vibrant arts centre. Featuring exhibitions and workshops, it showcases the creativity of regional artists, providing visitors with a unique cultural experience in the heart of Chestertown.

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

Flying into Chestertown, Maryland, is convenient with three major airports nearby. Washington, DC (DCA-Ronald Reagan Washington National) is situated 93km away, offering luxurious hotels such as InterContinental Washington D.C. - The Wharf and The Watergate Hotel, both easily accessible from the airport. Washington, DC (IAD-Washington Dulles Intl.) is located 122km away, with nearby options like Hyatt Regency Dulles International Airport. Closer to Chestertown, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is only 51km away, featuring high-end hotels like Four Seasons Hotel Baltimore, providing shuttle services to the airport. These airports ensure seamless travel for your visit to Chestertown.