Chestertown Hotels

Top reasons to visit Chestertown

• Historic Charm: Stroll through the picturesque streets of historic Chestertown, steeped in rich local heritage and charm.
• Outdoor Adventures: Engage in various outdoor activities amidst stunning scenery, perfect for nature enthusiasts and families.
• Serene Eastern Shore: Enjoy the tranquil beauty of the Eastern Shore, ideal for a relaxing getaway.
• Welcoming Accommodations: Choose from a variety of hotels, including pet-friendly and LGBTQIA-friendly options.
• Vibrant Local Culture: Experience the warm hospitality of friendly locals and immerse yourself in the vibrant culture of Chestertown.

Find great hotels near Chestertown

Discover a range of hotel accommodations in Chestertown, Maryland, ideal for both leisure and business travellers. From pet-friendly options to LGBTQIA welcoming environments, Chestertown's hotels cater to diverse needs. Whether you're seeking a comfortable motel or a charming hotel, you'll find the perfect base to explore this quaint town and its vibrant local culture.

• Quality Inn & Suites Bel Air I-95 Exit 77A: This budget-friendly hotel is situated 34km from Chestertown and caters to business travellers seeking a convenient stay. With comfortable accommodations and essential amenities, Quality Inn & Suites ensures a relaxed environment for work or leisure. Guests can enjoy complimentary breakfast, free Wi-Fi, and a well-equipped fitness centre, making it an excellent choice for those on a professional trip.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: Also located 34km from Chestertown, La Quinta Inn & Suites offers a welcoming atmosphere for pet lovers, with a guest rating of 8.2 out of 10. This budget-friendly hotel allows pets, providing a hassle-free experience for those travelling with furry companions. Amenities include complimentary breakfast, free Wi-Fi, and a fitness centre, creating a comfortable setting for both guests and their pets.
• Americas Best Value Inn Edgewood: Found 34km from Chestertown, Americas Best Value Inn Edgewood presents a budget-friendly option for those seeking a pet-friendly stay. With a focus on comfort and accessibility, this hotel allows pets on-site, with specific policies in place. Guests can benefit from free Wi-Fi, a continental breakfast, and a relaxed atmosphere, making it a suitable choice for travellers with pets in tow.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of historical charm and outdoor adventure. Stroll through the picturesque streets of historic Chestertown, where family-friendly activities abound. Explore the serene Eastern Shore, perfect for a relaxing getaway, and enjoy the warm hospitality of the friendly locals. Whether you're seeking scenic views or budget-friendly experiences, Chestertown's peaceful location invites you to unwind and discover its rich heritage.

• Worton: Located a mere 6km from Chestertown, Worton offers a serene escape into nature. The town is characterised by its seasonal visitor patterns, with peak times in April to May and July. Ideal for those seeking outdoor adventures, Worton is surrounded by beautiful beaches, lakes, and bays. Visitors can indulge in recreational activities and enjoy the scenic beauty that the area has to offer. Whether you're looking to hike, picnic, or simply soak in the tranquil atmosphere, Worton’s outdoor spaces provide a perfect backdrop for relaxation and exploration.
• Georgetown: Nestled within the Chestertown area, Georgetown is a charming village that attracts visitors primarily from June to August. Known for its romantic ambiance and outdoor activities, Georgetown invites couples and families alike to enjoy its recreation centre and picturesque hiking trails. The nearby beach and marina are perfect for water-based activities, while the national state park provides ample opportunities for nature walks and picnics. Georgetown is an ideal spot for those seeking both adventure and a peaceful retreat.
• Tolchester Beach: A delightful village within the Chestertown vicinity, Tolchester Beach sees a steady flow of visitors throughout the year, with a surge in popularity during May and the summer months. This coastal gem is celebrated for its stunning beaches and family-friendly atmosphere. Guests can partake in various outdoor activities, including skiing at local resorts during winter months. The beaches here are perfect for sunbathing and family outings, while the marina offers opportunities for boating and fishing. Tolchester Beach is a must-visit for those looking to embrace the great outdoors.

Things to do in Chestertown

Shopping

In Chestertown, you can explore local shops like The Bookplate, offering unique gifts and literature, and the Chestertown Farmers' Market for fresh produce and handmade items. If you're up for a drive, visit the nearby Centreville Shopping Centre, about 19km away, featuring various retail options and eateries.

Recreation

At the Well House in Chestertown, indulge in rejuvenating massage therapies and holistic wellness practices in a serene environment. For outdoor enthusiasts, the nearby Eastern Shore offers scenic trails for hiking and cycling, providing a refreshing escape into nature while promoting physical well-being.

Adventure

Explore the scenic Chester River by renting a kayak or paddleboard, offering an invigorating way to take in the natural beauty. For hiking enthusiasts, the nearby Eastern Neck National Wildlife Refuge provides trails with breathtaking views and opportunities to observe local wildlife.

Nightlife

Explore The Kitty Knight House on High Street for a charming riverside dining experience, then venture to The Chester River Yacht & Country Club for a relaxed evening by the water. For a lively atmosphere, check out The Fish Whistle, known for its vibrant nightlife and tasty seafood dishes.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, consider visiting during the off-peak months of January to February and November, when accommodation prices are lower. Tuesdays tend to be the cheapest days for stays, while Saturdays are the most expensive. Use Expedia’s search tool to find budget-friendly options and filter for eco-certified hotels. Combine your hotel booking with flights and activities for potential savings. Remember to sort the price filter from lowest to highest to uncover the best deals available.

• 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: Utilise Expedia’s search tool to customise your search according to your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will reveal sustainable and environmentally-friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can potentially save money by combining your hotel reservation in Chestertown with your flights and activities through an Expedia package.

Find the best attractions in Chestertown

Chestertown offers a delightful getaway for those seeking outdoor adventures, stunning scenery, and beach experiences. Visitors can explore parks, urban areas, and local beaches, making it an ideal destination for families. A must-see is the historic Chestertown, where you can immerse yourself in the rich local heritage while enjoying the beautiful surroundings.

• Sumner Hall: Immerse yourself in the rich history of the local area at Sumner Hall, a museum that celebrates the cultural heritage of Chestertown. Its exhibits provide a unique insight into the past, reflecting the community’s vibrant history and contributions.
• Wilmer Park: Enjoy the outdoors at Wilmer Park, a verdant urban park that offers family-friendly spaces for picnics and leisurely walks. With scenic views of the Chester River, it’s an ideal spot to relax and take in the natural beauty of the environment.
• River Arts Chestertown: Discover creativity at River Arts Chestertown, an arts centre showcasing the works of local artists. The atmosphere is vibrant and inspiring, making it a perfect place to appreciate and support the local arts scene.

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

To reach Chestertown, Maryland, you can fly into three major airports. Philadelphia International Airport (PHL) is situated 101km away, with excellent hotel options like the W Philadelphia and The Ritz-Carlton, both around 6-11km from the airport. Ronald Reagan Washington National Airport (DCA) is 93km away, offering luxurious stays at the InterContinental Washington D.C. - The Wharf and Pendry Washington DC - The Wharf, both within 2-6km of the airport. Lastly, Washington Dulles International Airport (IAD) is 122km away, with the Hyatt Regency Dulles International Airport and The Westin Dulles Airport conveniently located just 1-3km from the terminal.