Search Chestertown hotels

Top reasons to visit Chestertown

• Historic Downtown: Stroll through cobblestone streets lined with quaint shops and enjoy the rich history of this charming town.
• Scenic Beauty: Chestertown boasts picturesque views and outdoor activities, perfect for nature lovers and families alike.
• Vibrant Atmosphere: High Street offers a lively atmosphere with local events and performances, ideal for budget travellers.
• Relaxing Boardwalk: Unwind at the scenic boardwalk, perfect for leisurely walks and enjoying the tranquil waters.
• Diverse Accommodation: Find a range of welcoming lodging options, catering to all needs, including pet-friendly and LGBTQIA-friendly stays.

Find great hotels near Chestertown

Explore a range of accommodation options in Chestertown, Maryland, where you'll find welcoming hotels and motels perfect for any traveller. Whether you're seeking pet-friendly amenities, business-focused facilities, or an LGBTQIA-friendly environment, Chestertown has the ideal lodging for your needs. From comfortable suites to charming hotels, your stay in this picturesque town will be both enjoyable and memorable.

• Quality Inn & Suites Bel Air I-95 Exit 77A: Ideal for the business traveller, Quality Inn & Suites Bel Air I-95 Exit 77A is designed with convenience and productivity in mind. Located 33.8km from Chestertown, this hotel provides excellent amenities such as complimentary Wi-Fi, a business centre, and meeting facilities. Guests can enjoy a hearty breakfast to fuel their day, while comfortable rooms ensure a restful stay after a busy day of meetings. Its strategic location near I-95 allows for easy access to local businesses and attractions.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: For those who cherish the companionship of their pets while enjoying nature, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A is an excellent choice. Situated 33.8km from Chestertown, this hotel welcomes both dogs and cats, making it a perfect stop for pet owners. Guests can take advantage of nearby parks and natural reserves, while the hotel offers a comfortable stay with amenities like free breakfast and a fitness centre. The welcoming atmosphere is complemented by a pet-friendly policy, ensuring a delightful experience for all.
• Red Roof Inn Aberdeen: Located 35.4km from Chestertown, Red Roof Inn Aberdeen is not only pet-friendly but also embraces an inclusive atmosphere for LGBTQIA travellers. This hotel offers a comfortable and welcoming environment, allowing small pets, making it a great choice for those travelling with furry companions. Guests can look forward to amenities such as complimentary Wi-Fi and free coffee in the lobby. Its affiliation with LGBTQI travel guides ensures a friendly and accommodating experience for everyone.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of history and charm, perfect for a summer getaway. Explore the historic downtown, where cobblestone streets and quaint shops await. Discover the vibrant atmosphere along High Street, ideal for families and budget travellers alike. Enjoy the scenic beauty of the area, with opportunities for outdoor activities and relaxation. Whether you’re wandering through historic Chestertown or soaking up the friendly vibes, this destination promises an unforgettable experience.

• Worton: Located a mere 6.4km from Chestertown, Worton provides a delightful escape for outdoor enthusiasts. This charming city offers a moderately seasonal travel experience, peaking in April to May and July, making it ideal for those seeking beachside adventures and stunning scenery. Visitors can explore nearby beaches, marinas, and the expansive national state park, perfect for hiking and picnicking. Worton's recreational areas and educational venues make it a great spot for families and nature lovers alike.
• Georgetown: Nestled within the Chestertown area, the quaint village of Georgetown is known for its romantic charm and adventurous spirit. With peak travel from June to August, this village caters to those looking for outdoor activities and recreational opportunities. Visitors can engage in various sports at the local stadium and enjoy the national state park's beauty, making it perfect for couples and families. The area's scenic landscapes provide fantastic backdrops for memorable experiences.
• Tolchester Beach: A picturesque village close to Chestertown, Tolchester Beach is a hidden gem for beach lovers and outdoor adventurers alike. While it experiences a more consistent flow of visitors, it peaks in May and the summer months. The inviting boardwalk and recreational areas offer plenty of opportunities for relaxation and fun. With stunning beaches and a nearby marina, Tolchester Beach is an ideal spot for sunbathing, swimming, and enjoying the natural surroundings.

Things to do in and around Chestertown

Chestertown offers a delightful getaway with its scenic beauty and outdoor activities. Visitors can explore educational attractions, enjoy live music performances, and relax at the picturesque boardwalk. For those keen on camping, there are several campgrounds available. Whether you're after recreational areas or simply soaking in the local charm, Chestertown promises a memorable experience for all.

Shopping

In Chestertown, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, check out Queenstown Premium Outlets, 27.4km away, for a variety of brands. For more options, consider Westown, located 38.6km from Chestertown, offering a lovely mix of shops.

Recreation

Ripken Stadium, 35.4km from Chestertown, offers an energetic atmosphere with thrilling sports events. For golf enthusiasts, Queenstown Harbor Golf Club and Queenstown Harbor Golf Links, both 27.4km away, provide stunning outdoor settings, perfect for a relaxing day on the greens amidst beautiful landscapes.

Adventure

Emmorton Recreation & Tennis Center, located 38.6km from Chestertown, offers vibrant adventure vibes with various sporting activities. For water enthusiasts, Annapolis Sailing School, 45.1km away, provides thrilling sailing experiences amidst beautiful waters. Tose Family Tennis Center, also 45.1km from Chestertown, boasts exciting tennis activities in a lively atmosphere.

Nightlife

For a vibrant night in Chestertown, catch a show at the Garfield Center for the Arts, offering a mix of entertainment and culture. Alternatively, the Avalon Theatre and Milburn Stone Theater, both nearby, promise delightful performances in a charming setting, perfect for a romantic evening out.

Booking tips and Expedia advantages for Chestertown

When visiting Chestertown, Maryland, the best time to save money is during the off-peak months of January, February, and November, with Tuesdays being the cheapest days for accommodation. Avoid the pricier months of June, July, and October, and consider using Expedia to find budget-friendly lodging by filtering for eco-certified hotels. Look for package deals that combine flights, hotels, and activities for additional savings. Don't forget to explore free local attractions and use public transport for economical travel around the charming town.

• 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 options based on your budget, desired location, and preferred hotel style. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels currently available. To find the most affordable prices and deals, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can potentially save money by combining your Chestertown hotel booking with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chestertown

Chestertown offers a delightful blend of outdoor activities and scenic beauty, making it perfect for a family getaway. You can explore local beaches, parks, and urban parks, all designed for those seeking a refreshing beach experience. Whether you're enjoying the tranquil waters or wandering through lush green spaces, Chestertown has plenty to keep you entertained during your visit.

• Eastern Neck National Wildlife Refuge: Located 25.7km from Chestertown, this beautiful reserve offers a family-friendly atmosphere where you can explore diverse wildlife and scenic landscapes. Perfect for nature walks, birdwatching, and picnics, it’s a great spot to unwind and connect with nature.
• Washington College: Nestled in the heart of Chestertown, this historic college boasts stunning architecture and a lively cultural scene. Visitors can enjoy art exhibitions, lectures, and campus tours that showcase the college's rich history and academic vibrancy.
• Rolphs Wharf Marina: Situated within Chestertown, this marina is ideal for adventure seekers. Enjoy boating, fishing, and water sports, or simply relax by the beach and soak up the outdoor atmosphere, making it a perfect getaway for thrill-seekers.

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

Travelling to Chestertown, Maryland, is convenient with three major airports nearby. Washington, DC (DCA-Ronald Reagan Washington National) is 93.3km away, with luxurious hotels like the Salamander Washington DC and InterContinental Washington D.C. - The Wharf, both located 3.2km from the airport. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is closer at 33.2km, featuring top-notch accommodations such as the Four Seasons Hotel Baltimore and Sagamore Pendry Baltimore, both 12.9km away with comprehensive transport services. Lastly, Baltimore, MD (MTN-Martin State) is 32.2km from Chestertown, offering options like the Canopy by Hilton Baltimore Harbor Point and Hyatt Place Baltimore Inner Harbor, both 16.1km away.