Find hotels in Chestertown, MD from £46

Top reasons to visit Chestertown

• Historic Charm: Explore the picturesque streets adorned with colonial architecture, reflecting Chestertown's rich history.
• Outdoor Activities: Enjoy a variety of outdoor pursuits, from boating at Tolchester Marina to leisurely strolls along scenic waterfronts.
• Beautiful Parks: Relax in local parks and picnic areas, perfect for family gatherings amidst nature.
• Vibrant Community: Experience the warm hospitality of Chestertown, with welcoming accommodations for all types of travellers.
• Scenic Beauty: Revel in the stunning landscapes of the Eastern Shore, ideal for a relaxing getaway.

Find great hotels near Chestertown

Discover a charming selection of hotels in Chestertown, Maryland, perfect for every traveller. Whether you're seeking pet-friendly accommodations, business-themed stays, or LGBTQIA welcoming environments, Chestertown offers a variety of options to suit your needs. With its picturesque surroundings and warm hospitality, you're sure to find the best Chestertown hotels that provide a memorable vacation experience.

• Quality Inn & Suites Bel Air I-95 Exit 77A: Ideal for business travellers, Quality Inn & Suites Bel Air I-95 Exit 77A combines comfort with functionality. Located 13.0km from Chestertown, this hotel offers a range of services tailored to meet the needs of professionals on the go. Guests appreciate the well-equipped business centre, complimentary Wi-Fi, and meeting facilities. The hotel’s spacious rooms are designed for relaxation after a busy day, making it a perfect retreat for those looking to balance work and leisure.
• Red Roof Inn Aberdeen: Embracing inclusivity, Red Roof Inn Aberdeen is a welcoming haven for LGBTQIA travellers and their furry companions. Located 13.7km from Chestertown, this hotel is committed to providing a safe and friendly environment. It accommodates pets with specific policies in place, ensuring both human and animal guests feel at home. The property is known for its comfortable rooms and convenience, making it an ideal choice for those seeking a pet-friendly stay that celebrates diversity.
• Americas Best Value Inn Edgewood: Situated 13.0km from Chestertown, Americas Best Value Inn Edgewood is a charming option for pet owners looking for affordable lodging. This hotel allows pets and offers a friendly atmosphere for both guests and their four-legged friends. With flexible pet policies and comfortable rooms, it caters to those who appreciate convenience without compromising on quality. Guests enjoy easy access to local attractions while feeling at home in this welcoming environment.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of historical charm and outdoor adventures. Explore the picturesque streets lined with colonial architecture, or head to the nearby Tolchester Marina for a day of boating on the Chesapeake Bay. The Eastern Shore’s scenic beauty provides a perfect backdrop for family-friendly activities, making it an ideal destination for those seeking relaxation and friendly encounters. Discover the unique vibes of this charming town and its surrounding areas during your visit.

• Worton: Located a mere 2.5km from Chestertown, Worton offers a delightful escape for outdoor enthusiasts and nature lovers. The town boasts scenic landscapes, perfect for leisurely walks and picnics. Visitors flock here during spring and summer months for its vibrant recreational areas, including nearby beaches and marinas. Notable attractions include a national state park that invites exploration and adventure, making it an ideal spot for those wishing to soak in Maryland's natural beauty.
• Georgetown: Nestled within the vicinity of Chestertown, Georgetown is a charming village that attracts visitors with its outdoor experiences and romantic settings. Peak travel times occur during the warm summer months, when guests can enjoy various recreational activities. The village is home to a sports facility stadium and access to a national state park, both of which are perfect for those seeking an active holiday. The quaint atmosphere combined with adventurous pursuits makes Georgetown a lovely addition to your itinerary.
• Tolchester Beach: This picturesque village, located close to Chestertown, is a hidden gem for beach lovers and outdoor adventurers alike. Tolchester Beach sees a consistent flow of visitors, particularly in late spring and summer. The scenic boardwalk along the beach invites leisurely strolls, while the proximity to marinas and a national state park enhances its appeal. With its inviting atmosphere and beautiful landscapes, Tolchester Beach is perfect for a relaxing day by the water or an adventure-filled outing.

Things to do in and around Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor activities and scenic beauty, perfect for a relaxing holiday. Visitors can enjoy educational experiences, explore recreational areas, and stroll along the picturesque boardwalk. A highlight for families and friends is the picnic area, ideal for enjoying a leisurely meal amidst nature. Chestertown promises a charming getaway filled with enjoyable activities and beautiful landscapes.

Shopping

In Chestertown, you can enjoy quaint shops for unique gifts. If you're up for a drive, visit Queenstown Premium Outlets for a variety of brands, 10.6km away, or explore Westown, a family-friendly shopping centre, 14.9km away, offering a great mix of stores.

Recreation

Experience the energetic atmosphere at Ripken Stadium, only 13.7km from Chestertown, where you can enjoy various sporting events. Alternatively, Queenstown Harbor Golf Club and Queenstown Harbor Golf Links, both 10.6km away, offer stunning outdoor settings for a round of golf amidst beautiful landscapes.

Adventure

Explore the Emmorton Recreation & Tennis Center, 14.9km from Chestertown, for thrilling tennis matches and recreational activities. Experience the Annapolis Sailing School, 17.4km away, where you can enjoy sailing lessons amidst scenic waters. Alternatively, head to the Tose Family Tennis Center, also 17.4km distant, for more tennis excitement.

Nightlife

In Chestertown, the Garfield Center for the Arts at the Prince Theatre offers a vibrant cultural experience, while the nearby Church Hill Theatre and Everett Theatre provide additional entertainment options, all featuring a charming atmosphere perfect for families and couples seeking a delightful night out.

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 or November, when accommodation rates are lower. Booking your stay on a Tuesday can also yield savings compared to weekends. Use Expedia’s search tool to find budget-friendly hotel options, and don't forget to check for military discounts. Combine your hotel with flights and activities for additional savings. For free activities, explore the charming town and its scenic waterfront. Planning your visit during these times can significantly enhance your budget while enjoying Chestertown's offerings.

• 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 budget, desired location, and the type of hotel you favour. To discover the most affordable prices and offers, arrange 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 through an Expedia package.

Find the best attractions in Chestertown

Chestertown offers a delightful blend of outdoor activities and scenic beauty, making it perfect for a beachside family holiday. Visitors can explore the charming historic district, relax in local parks, and enjoy the picturesque waterfront. For those keen on outdoor adventures, the area boasts beautiful beaches and urban parks, providing ample opportunities for relaxation and recreation amidst stunning surroundings.

• Washington College: Nestled in the heart of Chestertown, Washington College boasts a rich history and vibrant campus life, offering a unique blend of academic excellence and cultural events. Stroll through its picturesque grounds and enjoy the charming architecture that reflects its storied past.
• Rolphs Wharf Marina: For those seeking adventure, Rolphs Wharf Marina is a haven for outdoor enthusiasts. Engage in various water activities, relax by the beach, or simply soak in the stunning views of the Chester River, making it an ideal spot for a day of exploration.
• Historical Society of Kent County Maryland: Immerse yourself in the local heritage at the Historical Society of Kent County Maryland. This museum offers fascinating exhibits that illuminate the region's history, culture, and traditions, providing a deeper understanding of Chestertown's past.

Best time to go to Chestertown

The best time to visit Chestertown is dependant 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	Slightly High
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	Average
November	47.3°F (8.5°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	40.1°F (4.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

The nearest major airports for your trip to Chestertown

To reach Chestertown, Maryland, tourists can fly into several major airports. Washington, DC (DCA - Ronald Reagan Washington National) is situated 36.0km away, with luxurious hotels like Salamander Washington DC and InterContinental Washington D.C. - The Wharf, both only 1.2km from the airport. Baltimore, MD (BWI - Baltimore Washington International Thurgood Marshall) is closer at 31.2km, featuring exquisite options such as Sagamore Pendry Baltimore and The Ivy Hotel. Alternatively, Baltimore, MD (MTN - Martin State) is 12.4km away, offering accommodations like Canopy by Hilton Baltimore Harbor Point and Hyatt Place Baltimore Inner Harbor. Each airport provides convenient access to the respective hotels for a comfortable stay.