Find hotels in Chestertown, MD from NT$1,895

Top reasons to visit Chestertown

• Historic Charm: Explore the quaint streets of Chestertown, rich in history and lined with charming architecture.
• Outdoor Activities: Enjoy scenic parks and beautiful waterfront views, perfect for hiking, picnicking, and relaxation.
• Family-Friendly Atmosphere: Chestertown is welcoming for families, offering engaging activities and events for all ages.
• Local Attractions: Experience unique local events and nearby attractions that highlight the region's culture and history.
• Comfortable Accommodations: Choose from a variety of comfortable lodging options, catering to diverse traveler needs.

Find great hotels near Chestertown

Discover a range of comfortable accommodations in Chestertown, Maryland, perfect for every type of traveler. Whether you're seeking pet-friendly options, business facilities, or a welcoming atmosphere for LGBTQIA visitors, Chestertown hotels offer something for everyone. Enjoy a delightful stay in this charming town with various hotel and motel choices to suit your needs.

• Quality Inn & Suites Bel Air I-95 Exit 77A: This budget-friendly hotel is designed for travelers seeking a practical and comfortable stay. Located 34km from Chestertown, Quality Inn & Suites provides a convenient base for business travelers. Guests can enjoy amenities such as free Wi-Fi, complimentary breakfast, and an on-site business center, making it easy to stay productive during your visit. The rooms are well-appointed and feature modern furnishings, ensuring a restful experience after a day of meetings or exploring the local area.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: La Quinta Inn & Suites offers a welcoming environment for both travelers and their pets, with a guest rating of 8.2 out of 10. Situated 34km from Chestertown, this pet-friendly property allows pets with specific guidelines. Guests can take advantage of amenities such as a complimentary breakfast, free Wi-Fi, and an outdoor pool. The inviting rooms are designed for comfort, ensuring that both you and your furry friends feel right at home during your stay.
• Americas Best Value Inn Edgewood: Located 34km from Chestertown, Americas Best Value Inn Edgewood is an affordable option for those traveling with pets. This budget-friendly hotel allows pets with certain fees and policies in place. Guests appreciate the straightforward accommodations, which include free Wi-Fi and parking. The cozy rooms provide a comfortable retreat after a day of sightseeing or business activities, making it a practical choice for travelers looking for convenience and value.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of historical charm and outdoor adventure. Stroll through the quaint streets of historic Chestertown, where family-friendly vibes abound. Enjoy the scenic beauty of the Eastern Shore while exploring peaceful parks and waterfront views. Nearby attractions provide a relaxing atmosphere perfect for budget-conscious travelers looking to unwind. Whether you're discovering local history or soaking in the natural surroundings, Chestertown promises an unforgettable experience.

• Worton: Located just 6km from Chestertown, Worton offers travelers a charming escape with its scenic beauty and outdoor adventures. This city attracts visitors year-round, with peak arrivals in April to May and July, making it an ideal destination for nature lovers. Enjoy recreational activities in local parks or explore the nearby beach, bay, and lake. Worton’s captivating scenery and outdoor experiences provide a perfect backdrop for relaxation and exploration.
• Georgetown: Nestled in the vicinity of Chestertown, Georgetown is a quaint village known for its romantic atmosphere and outdoor entertainment. With peak visitor numbers from June to August, this destination is perfect for couples and families alike. Enjoy a variety of activities including hiking trails and visits to the recreation center. The nearby beach, marina, and national state park offer ample opportunities to immerse yourself in nature and enjoy the beautiful surroundings.
• Tolchester Beach: A delightful village close to Chestertown, Tolchester Beach is not heavily seasonal, making it an attractive option for travelers year-round. Visitors flock here primarily in May and during the summer months of July to August for its stunning beaches and family-friendly environment. Engage in outdoor activities, visit the local marina, or enjoy the nearby ski resort during winter months. The picturesque landscapes and serene beaches make Tolchester Beach a perfect spot for relaxation and family fun.

Things to do in Chestertown

Shopping

In downtown Chestertown, explore local boutiques like The Blue Heron, offering unique gifts and art. If you're up for a drive, check out the larger shopping options at the nearby Kent Island Shopping Center, featuring various retailers for a broader selection of souvenirs.

Recreation

In Chestertown, the Spa at the Inn at Mitchell House offers a serene atmosphere with personalized treatments, perfect for rejuvenation. Nearby, the Chester River Yacht and Country Club features scenic views and recreational activities like golfing and kayaking, providing a refreshing escape into nature.

Adventure

Explore the scenic Chester River by kayaking or paddleboarding, allowing you to experience the tranquility of nature up close. For a thrilling ride, consider a guided boat tour that showcases the area's wildlife and historic landmarks while you enjoy the beautiful waterways.

Nightlife

Chestertown's nightlife offers a cozy charm, with venues like The Garfield Center for the Arts showcasing local performances. For a relaxed evening, visit The Fish Whistle for waterfront dining and drinks, or enjoy a craft beer at the nearby Chester River Brewing Company.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, plan your visit between January to February or November for the lowest rates. Tuesdays offer the cheapest hotel stays, while Saturdays tend to be the most expensive. Use Expedia’s search tool to find budget-friendly accommodation by sorting options from lowest to highest price. Consider booking a package that combines your hotel, flights, and activities for additional savings. Explore the town on foot to avoid transportation costs, and take advantage of free local attractions to enhance your experience without breaking the bank.

• 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: Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred hotel type. To find the best prices and deals available, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay in Chestertown with your flights and activities by booking a package through Expedia.

Find the best attractions in Chestertown

Chestertown, Maryland, offers a delightful vacation for outdoor enthusiasts and families, featuring scenic parks and beautiful beach areas. Visitors can explore the historic charm of Chestertown while enjoying various outdoor activities. For a relaxing day, consider visiting local parks or taking a stroll along the waterfront. Whether you're seeking adventure or a peaceful retreat, Chestertown provides a perfect blend of experiences for every traveler.

• Historical Society of Kent County Maryland: Dive into the rich history of Kent County at this engaging museum. Explore unique exhibits that showcase local artifacts, documents, and stories that highlight the region's cultural heritage.
• Wilmer Park: Enjoy a relaxing day outdoors at this urban park, perfect for families and picnics. With scenic views along the waterfront, walking paths, and play areas, it's a lovely spot to unwind and soak up the local community atmosphere.
• River Arts Chestertown: Immerse yourself in the local art scene at this vibrant arts center. Featuring rotating exhibits, workshops, and community events, River Arts offers a creative space for artists and art lovers alike.

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

Traveling to Chestertown, Maryland, is convenient with several major airports nearby. Philadelphia International Airport (PHL) is 101km away, with luxurious accommodations like the W Philadelphia, The Ritz-Carlton, and The Rittenhouse, all within 11km of the airport. Washington, D.C. offers two options: Ronald Reagan Washington National Airport (DCA) is 93km away, with nearby hotels including the InterContinental Washington D.C. - The Wharf and The Watergate Hotel; both are just a few miles from the airport. Alternatively, Washington Dulles International Airport (IAD) is 122km away, with excellent choices like the Hyatt Regency and The Westin, located only 2km from the airport.