Search Chestertown hotels

Top reasons to visit Chestertown

• Historic Charm: Wander through the quaint streets of Chestertown, where rich heritage and vibrant community life create a unique atmosphere.
• Scenic Outdoor Activities: Enjoy delightful outdoor adventures, including leisurely walks along the waterfront and exploring charming parks.
• Family-Friendly Attractions: Engage in a variety of activities suitable for all ages amidst the peaceful landscapes of the Eastern Shore.
• Welcoming Accommodation: Choose from a range of hotels and motels that cater to diverse needs, including pet-friendly and LGBTQIA-friendly options.
• Thrilling Events: Experience exciting local events, such as motor racing, that add to the lively atmosphere of Chestertown.

Find great hotels near Chestertown

Chestertown, Maryland, offers a variety of accommodation options, from charming hotels to convenient motels, catering to diverse traveller needs. Whether you're seeking a pet-friendly stay, a welcoming environment for LGBTQIA guests, or facilities suited for business travel, Chestertown has you covered. Explore the local hotels and find the perfect place to unwind after a day of enjoying this picturesque town’s rich history and vibrant culture.

• Quality Inn & Suites Bel Air I-95 Exit 77A: Situated 33.8km from Chestertown, the Quality Inn & Suites Bel Air I-95 Exit 77A offers a practical stay for those seeking a budget-friendly option tailored for business travellers. The hotel features comfortable rooms equipped with modern amenities, including complimentary Wi-Fi and a business centre, ensuring that you can stay productive during your visit. Guests can enjoy a hearty breakfast to start their day, and the hotel's convenient location near I-95 allows for easy access to local attractions.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: Also located 33.8km from Chestertown, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A stands out for its welcoming atmosphere and pet-friendly policies, making it ideal for travellers who wish to bring their furry companions along. With a guest rating of 8.2 out of 10, this hotel features comfortable accommodations, free breakfast, and amenities specifically designed for pets, such as designated areas for walking them. The friendly staff is attentive, ensuring a pleasant stay for both guests and their pets.
• Americas Best Value Inn Edgewood: Just 33.8km from Chestertown, the Americas Best Value Inn Edgewood caters to budget-conscious travellers who also wish to bring their pets. This hotel provides essential amenities, including complimentary breakfast and Wi-Fi, while allowing pets with certain restrictions and fees. The welcoming environment and straightforward accommodations make it a suitable choice for those looking for comfort without breaking the bank. Guests appreciate the accessibility to local sites and the straightforward service.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of historical charm and outdoor adventures. Explore the scenic Eastern Shore, where family-friendly activities abound amidst a peaceful setting. Stroll through historic Chestertown's quaint streets, soaking in the friendly atmosphere. Nearby, you'll discover budget-friendly options and a welcoming community, making it an ideal getaway for relaxation and exploration. Experience the unique vibes that this lovely city and its surroundings have to offer on your holiday.

• Worton: Situated a mere 6.4km from Chestertown, Worton is a charming village that offers a delightful outdoor experience. With a seasonal influx of visitors peaking from April to May and during the summer months, it’s a perfect spot for those seeking beach scenery and recreational activities. Explore the local outdoor areas, or take a leisurely stroll near the picturesque bay and lake. Whether you’re indulging in water sports or simply relishing the natural beauty, Worton provides a refreshing escape for nature lovers.
• Georgetown: Nestled within the Chestertown area, Georgetown is a quaint village that draws visitors for its romantic ambiance and entertaining activities. Peak seasons from June to August make it an ideal summer getaway. The village boasts a recreation centre and scenic hiking trails, perfect for those keen on exploring the great outdoors. With nearby attractions such as a beach, marina, and national state park, Georgetown offers a fantastic blend of relaxation and adventure, making it a must-visit on your itinerary.
• Tolchester Beach: As a charming village close to Chestertown, Tolchester Beach is known for its beautiful natural landscapes and family-friendly beaches. While it doesn’t follow a strict seasonal pattern, the peak visitor times are during May and the summer months of July to August. Enjoy thrilling outdoor activities, relax at the family beach, or visit the local marina for a day of fun on the water. The area is perfect for those looking to unwind and soak up the sun while experiencing the scenic beauty of the shore.

Things to do in Chestertown

Shopping

In the heart of Chestertown, you can explore local boutiques and artisan shops for unique gifts and souvenirs. If you're up for a drive, consider visiting the nearby Kent Island Shopping Centre for a broader selection of shops and dining options.

Recreation

In Chestertown, the Haven Spa offers a tranquil atmosphere with a variety of holistic treatments, including massages and facials. Nearby, the Chester River provides opportunities for kayaking and paddleboarding, allowing you to connect with nature while enjoying the scenic waterways of Maryland.

Adventure

In Chestertown, explore the scenic Chester River by kayaking or paddleboarding, offering a unique perspective of the area's natural beauty. For land adventures, hike the trails at nearby Sassafras Natural Resource Management Area, where you can enjoy diverse wildlife and picturesque landscapes.

Nightlife

In Chestertown, The Garfield Center for the Arts hosts live performances, showcasing local talent and theatre productions. The downtown area features charming pubs and bars, offering a relaxed atmosphere for enjoying craft beers and socialising with locals.

Find the best attractions in Chestertown

Chestertown offers a delightful blend of outdoor adventures and scenic beauty, perfect for families and beach lovers alike. Explore the charming parks and urban spaces, or soak up the sun at nearby beaches. Don’t miss the opportunity to visit historic Chestertown, where rich heritage meets vibrant community life. Whether you’re looking for relaxation or exploration, Chestertown has something for everyone.

• Historical Society of Kent County Maryland: Immerse yourself in the rich history of the region at this charming museum. Explore exhibits that showcase local heritage and cultural artefacts, offering a glimpse into Chestertown's past and its significance in Maryland's history.
• Wilmer Park: A delightful urban park ideal for families, Wilmer Park boasts scenic walking paths and open spaces for picnics. Enjoy the lush greenery while taking in views of the Chester River, making it a lovely spot for relaxation and outdoor activities.
• River Arts Chestertown: Engage with local artists and their creations at this vibrant arts centre. River Arts hosts exhibitions, workshops, and community events, allowing visitors to appreciate and participate in the thriving arts scene 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 nearby airports such as Philadelphia International Airport (PHL), located 101.4km away, and Ronald Reagan Washington National Airport (DCA), which is 93.3km away. Excellent accommodation options near PHL include the 5-star W Philadelphia and The Rittenhouse, both about 9.7km from the airport. For DCA, the 5-star InterContinental Washington D.C. - The Wharf is only 3.2km away. Additionally, Washington Dulles International Airport (IAD) is 122.3km from Chestertown, with nearby hotels like the 4-star Hyatt Regency just 1.6km away. Each airport offers various transport options to easily access Chestertown.