Find hotels in Chestertown, MD from £52

Top reasons to visit Chestertown

• Historic Charm: Stroll through the picturesque streets of historic Chestertown, rich in heritage and character.
• Outdoor Activities: Enjoy a variety of outdoor pursuits, from nature walks to beach outings along the scenic Eastern Shore.
• Family-Friendly Attractions: Discover numerous attractions suitable for families, ensuring entertainment for all ages.
• Welcoming Community: Experience the warm and friendly atmosphere of Chestertown, making you feel right at home.
• Diverse Accommodation: Choose from a range of lodging options, including pet-friendly and LGBTQIA-friendly establishments.

Find great hotels near Chestertown

Discover a charming selection of hotels and motels in Chestertown, Maryland, tailored to meet the diverse needs of every traveller. Whether you're seeking pet-friendly accommodations, facilities for business travel, or a welcoming environment for the LGBTQIA community, you'll find the perfect spot to relax and unwind. Explore the best lodging options near Chestertown and enjoy a delightful stay in this picturesque town.

• Quality Inn & Suites Bel Air I-95 Exit 77A: This budget-friendly hotel provides a convenient lodging option for business travellers seeking comfort and accessibility. Located 33.8km from Chestertown, Quality Inn & Suites Bel Air offers essential amenities designed for a productive stay. Guests can enjoy complimentary breakfast, free Wi-Fi, and a well-equipped business centre. The hotel's straightforward approach combines practicality with affordability, ensuring a pleasant experience for those on work-related visits.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: With a commendable guest rating of 8.2, this welcoming hotel caters particularly well to pet owners. Situated 33.8km from Chestertown, La Quinta Inn & Suites is a pet-friendly haven, allowing guests to bring their furry companions along for the adventure. The amenities include a complimentary breakfast, fitness centre, and free Wi-Fi. Its warm atmosphere and accommodating pet policies make it an ideal choice for travellers looking to explore the area with their pets.
• Americas Best Value Inn Edgewood: Another budget-friendly option, Americas Best Value Inn Edgewood is perfect for travellers with pets, allowing dogs and cats on the premises. Located 33.8km from Chestertown, the hotel features comfortable accommodations and essential amenities, including free Wi-Fi and on-site parking. The flexible pet policy, which includes a variable fee, makes it easy for pet owners to enjoy their stay. This property offers a relaxed environment that prioritises both comfort and affordability.

Where to stay in and around Chestertown

Chestertown, Maryland, is a delightful blend of history and natural beauty, perfect for a relaxing getaway. Explore the charming streets of historic Chestertown, where family-friendly attractions abound. The Eastern Shore offers tranquil scenery, ideal for outdoor enthusiasts. Venture into nearby towns to experience a warm, welcoming atmosphere and budget-friendly options, making it an ideal destination for a peaceful retreat. Enjoy the local culture and the friendly people that make this region truly special.

• Worton: Situated a mere 6.4km from Chestertown, Worton offers a charming blend of outdoor adventures and picturesque scenery. Visitors flock here during the peak months of April to May and July, drawn by its recreational areas and stunning natural landscapes. Whether you fancy a day at the beach, a stroll by the bay, or a serene afternoon by the lake, Worton provides a wealth of options for relaxation and exploration. With its seasonal visitor trends, it’s the perfect getaway for nature enthusiasts looking to unwind in a tranquil setting.
• Georgetown: Nestled conveniently within the Chestertown area, Georgetown is a quaint village that attracts visitors primarily from June to August. Known for its romantic atmosphere and entertainment offerings, this village boasts a recreation centre and scenic hiking trails that cater to outdoor lovers. The nearby beach and marina offer splendid opportunities for water activities, while the proximity to a national state park allows for further exploration of Maryland's natural beauty. Georgetown is an ideal stop for those seeking both adventure and relaxation in a charming small-town setting.
• Pomona: A delightful village located close to Chestertown, Pomona welcomes travellers year-round, with a slight peak in visitor numbers during the summer months of June to August. Known for its family-friendly atmosphere, Pomona features a shopping centre and golf facilities that cater to a variety of interests. The local parks and nearby beach provide ample space for outdoor activities, making it a great destination for families looking to enjoy quality time together. With its accessible amenities and relaxed vibe, Pomona is perfect for those seeking a leisurely escape.

Things to do in Chestertown

Chestertown offers a delightful escape for those seeking outdoor adventures and scenic beauty. Visitors can enjoy a variety of activities, from educational experiences to motor racing events, making it an ideal destination for both relaxation and excitement. The town's charm and natural surroundings provide a perfect backdrop for a memorable holiday.

Shopping

In Chestertown, visit local shops like the Imperial Hotel Gift Shop for unique souvenirs and artisan goods. If you're up for a drive, head to the nearby Annapolis Mall, around 48.3km away, boasting a wide selection of national retailers and dining options for a full shopping day.

Recreation

Serenity Spa offers a tranquil environment with soothing treatments, including massages and facials, perfect for rejuvenation. For outdoor relaxation, visit Wilmer Park, featuring scenic views, walking paths, and picnic areas, ideal for unwinding amidst nature's beauty.

Adventure

In Chestertown, explore the scenic Chester River by kayaking or paddleboarding, offering a thrilling way to experience the area's natural beauty. For a unique adventure, try the local bike trails that wind through picturesque landscapes, perfect for enjoying the fresh air and charming surroundings.

Nightlife

Chestertown offers a charming nightlife with venues like the historic Garfield Centre for the Arts, hosting live performances, and the relaxed atmosphere at the Fish Whistle, perfect for unwinding with local brews. For a lively evening, explore the vibrant local bars along High Street.

Booking tips and Expedia advantages for Chestertown

• 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 refine your preferences, such as your budget, favoured location, and the type of hotel you desire. To discover the best prices and deals, 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 blend of outdoor activities, scenic views, and family-friendly experiences. Visitors can explore urban parks, marinas, and the charming historic district. The area is perfect for those seeking beach outings and nature walks, making it an ideal destination for a relaxing vacation. Don't miss the opportunity to visit historic Chestertown for a taste of its rich heritage.

• Historical Society of Kent County Maryland: Discover the rich heritage of the region at this engaging museum. With various exhibits and historical artefacts, it offers a fascinating glimpse into Kent County's past, making it a must-visit for history enthusiasts.
• Wilmer Park: This charming urban park is perfect for family outings and leisurely strolls. Enjoy its scenic views, playgrounds, and picnic areas, providing a delightful space to relax amidst nature in the heart of Chestertown.
• River Arts Chestertown: Immerse yourself in the vibrant local arts scene at this arts centre. Featuring diverse exhibitions and workshops, it showcases the creativity of local artists and offers a platform for cultural engagement.

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

When planning your visit to Chestertown, Maryland, you have several airports to consider. Philadelphia International Airport (PHL) is approximately 101.4km away, with luxury accommodation options such as the W Philadelphia and The Rittenhouse, both within 9.7km of the airport. Alternatively, Ronald Reagan Washington National Airport (DCA) is 93.3km away, offering nearby hotels like the InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both just 3.2km distant. Lastly, Washington Dulles International Airport (IAD) is 122.3km away, with convenient stays at The Westin Washington Dulles Airport and Hyatt Regency Dulles International Airport, both a mile from the terminal.