Find hotels in Chestertown, MD from ￥8,000

Top reasons to visit Chestertown

• Charming Historic Streets: Explore the picturesque streets of Chestertown, filled with friendly locals and rich culture.
• Outdoor Adventures: Enjoy a variety of outdoor activities in beautiful parks and scenic landscapes.
• Family-Friendly Activities: Chestertown offers numerous attractions perfect for families seeking fun and relaxation.
• Unique Accommodation Options: Find diverse lodging choices, from pet-friendly hotels to welcoming spaces for all travelers.
• Nearby Beaches: Take advantage of the close proximity to beautiful beaches for a perfect day of sun and sand.

Find great hotels near Chestertown

Discover a variety of accommodation options in Chestertown, Maryland, perfect for every type of traveler. Whether you're looking for pet-friendly hotels, convenient motels, or welcoming spaces for LGBTQIA guests, Chestertown offers a range of choices to meet your needs. Enjoy a comfortable stay while exploring the charming town and its rich history, making it an ideal destination for leisure or business travel.

• Quality Inn & Suites Bel Air I-95 Exit 77A: This budget-friendly hotel offers a practical choice for business travelers seeking comfort and convenience. Located 34km from Chestertown, the Quality Inn & Suites features well-appointed rooms equipped with essential amenities such as free Wi-Fi, a complimentary breakfast, and a fitness center for those looking to stay active. The property provides easy access to I-95, making it a great base for exploring the surrounding area while ensuring a comfortable stay for work-related trips.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: With a guest rating of 8.2 out of 10, La Quinta Inn & Suites is a welcoming choice for travelers looking for a pet-friendly experience. Situated 34km from Chestertown, this hotel allows pets on-site, accommodating dogs and cats with a specific pet policy. Guests appreciate amenities such as a complimentary breakfast, an outdoor pool, and spacious rooms designed for relaxation. The hotel’s location near the highway provides easy access to local attractions while ensuring a comfortable stay for both you and your furry friends.
• Americas Best Value Inn Edgewood: This budget-friendly hotel also caters to pet owners, making it a suitable option for those who wish to travel with their pets. Located 34km from Chestertown, Americas Best Value Inn offers essential amenities including free Wi-Fi and comfortable rooms. With a flexible pet policy, the hotel welcomes dogs and cats, ensuring a hassle-free experience for pet lovers. Its convenient location provides easy access to nearby attractions, making it a practical choice for visitors looking for value and comfort.

Where to stay in and around Chestertown

Chestertown, Maryland, offers an inviting blend of history and natural beauty, making it a perfect destination for outdoor enthusiasts and families alike. Explore the charming streets of historic Chestertown, where friendly locals welcome you to experience the rich culture and serene atmosphere of the Eastern Shore. With its peaceful location and family-friendly activities, Chestertown is an ideal base for discovering nearby attractions and enjoying the scenic landscapes that define this picturesque region.

• Worton: Located a mere 6km from Chestertown, Worton is a charming city that offers a delightful outdoor experience. With its visitor numbers peaking in the spring and summer months, it attracts travelers looking to enjoy its beautiful scenery and recreational areas. Worton is perfect for those seeking adventure in nature, with access to nearby lakes, bays, and beaches. Whether you're hiking or simply enjoying a picnic, this area provides a refreshing escape with plenty of opportunities for exploration.
• Georgetown: Nestled in the vicinity of Chestertown, Georgetown is a picturesque village that exudes a romantic charm. The village sees a rise in visitors during the summer months, making it an ideal spot for outdoor enthusiasts and those seeking entertainment. With a recreation center, hiking trails, and proximity to a national state park, Georgetown offers activities for everyone. Couples can enjoy serene walks along the beach or marina, while families can immerse themselves in the area's educational attractions.
• Tolchester Beach: A quaint village also near Chestertown, Tolchester Beach is known for its beautiful shores and vibrant outdoor scenery. Although its visitor numbers are fairly steady year-round, it tends to attract more guests during the warmer months, particularly in May and summer. This destination is perfect for beach lovers and families, offering a family-friendly beach experience along with nearby marinas. Outdoor activities abound, including skiing opportunities during the winter, making it a versatile spot for year-round fun.

Things to do in Chestertown

Shopping

In Chestertown, you can explore local shops like The Finishing Touch for unique gifts and souvenirs. If you're up for a drive, check out the Kent Island Shopping Center for a variety of retail options and dining experiences.

Recreation

In Chestertown, the Water's Edge Spa offers rejuvenating treatments in a serene riverside setting, ideal for relaxation. Participate in yoga sessions at the local wellness studio, where classes cater to various levels, allowing you to connect with your mind and body amidst a peaceful atmosphere.

Adventure

Explore the beautiful Chester River by kayaking or paddleboarding, where you can enjoy the scenic views and spot local wildlife. The nearby trails offer hiking opportunities through lush landscapes, inviting you to discover the natural beauty of the area while staying active and engaged.

Nightlife

Explore the lively atmosphere at The Fish Whistle, where you can enjoy fresh seafood and waterfront views. For a cozy vibe, visit the Chestertown Coffee Company, perfect for sipping artisanal drinks while catching up with friends or enjoying local art displays.

Find the best attractions in Chestertown

Chestertown, Maryland, is an ideal destination for outdoor enthusiasts and families seeking beach and scenic experiences. Visitors can explore beautiful parks, urban spaces, and nearby beaches while also taking time to discover the historic charm of Chestertown itself. With a variety of attractions that cater to outdoor adventures and relaxation, this charming town ensures a memorable vacation for everyone.

• Crumpton Auction: Experience a lively atmosphere at Crumpton Auction, where you can browse unique items and antiques in a family-friendly setting. This auction offers a glimpse into local culture and community engagement, making it a memorable stop.
• Historical Society of Kent County Maryland: Delve into the rich history of the region at the Historical Society of Kent County Maryland. This museum features exhibits that showcase the area's culture and heritage, providing fascinating insights into local life through the ages.
• Wilmer Park: Enjoy the outdoors at Wilmer Park, an urban oasis perfect for families. The park offers scenic views, walking paths, and recreational areas, making it ideal for a leisurely day out amidst nature.

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, offering luxurious hotels such as the 5-star W Philadelphia and The Ritz-Carlton, both within 11km. Ronald Reagan Washington National Airport (DCA) is 93km from Chestertown, with excellent accommodations like the 5-star InterContinental Washington D.C. - The Wharf, just 3km away. Additionally, Washington Dulles International Airport (IAD) is situated 122km from Chestertown, with nearby options including the 4-star Hyatt Regency Dulles International Airport, only 2km away. Each airport provides easy access to these quality hotels for a comfortable stay.