Chestertown Hotels

Top reasons to visit Chestertown

• Historic Charm: Stroll through the quaint streets of Chestertown, rich in history and character, offering a peaceful atmosphere.
• Outdoor Adventures: Enjoy a range of recreational activities in urban parks and nearby beaches, perfect for nature enthusiasts.
• Cultural Experiences: Engage with local arts and participate in community events, showcasing the town's vibrant culture.
• Family-Friendly Attractions: Explore educational and fun attractions suitable for all ages, ensuring memorable family outings.
• Diverse Accommodation: Choose from a variety of welcoming lodgings, catering to different preferences and budgets.

Find great hotels near Chestertown

Chestertown, Maryland, offers a delightful array of accommodation options for every traveller. Whether you seek pet-friendly hotels, business-oriented facilities, or LGBTQIA welcoming environments, you'll find something to suit your needs. From charming motels to well-appointed suites, the area boasts some of the best hotels, complete with glowing reviews. Discover the perfect place to unwind while exploring the picturesque surroundings of this historic town.

• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: This hotel is a welcoming retreat for travellers seeking a pet-friendly atmosphere. Located 33.8km from Chestertown, it features a range of amenities that cater to both human and furry guests. The property permits dogs and cats, ensuring that no family member is left behind. Guests appreciate the relaxed environment, with facilities that include complimentary breakfast, free Wi-Fi, and a fitness centre. The hotel balances comfort and convenience, making it an ideal choice for those embarking on a road trip or family getaway.
• Americas Best Value Inn Edgewood: Situated 33.8km from Chestertown, this hotel is perfect for those travelling with pets. Known for its affordability, it offers a no-fuss experience with essential amenities. Pets are welcome with a variable fee, allowing flexibility for families on the move. Guests enjoy comfortable rooms equipped with free Wi-Fi and cable television. The hotel’s convenient location near major transport routes makes it a strategic base for exploring the region while providing a homely feel for both guests and their pets.
• Extended Stay America Suites Baltimore Bel Air Aberdeen: This property, located 33.8km from Chestertown, caters to extended stays and those wishing to travel with their pets. With a focus on home-like comfort, the hotel features fully equipped kitchens in each suite, allowing guests to prepare their own meals. Pets are permitted with certain restrictions, creating a friendly environment for animal lovers. Amenities such as free Wi-Fi, on-site laundry facilities, and a fitness centre make this hotel a practical choice for long-term stays or family visits, ensuring all guests feel at home.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor adventures and historical charm, making it an ideal destination for family-friendly getaways. Explore the historic streets of Chestertown, where low crowds allow for a relaxing atmosphere. Venture into the scenic Eastern Shore region, renowned for its friendly locals and rich heritage. Whether you're seeking budget-friendly options or memorable experiences, Chestertown promises a unique escape filled with warm hospitality and captivating sights.

• Worton: Located a mere 6.4km from Chestertown, Worton is a charming city that offers a delightful blend of outdoor experiences and scenic beauty. Known for its moderately seasonal traveller arrivals, Worton attracts visitors mainly during the spring and summer months. The area is perfect for outdoor enthusiasts, with numerous recreational activities available, including hiking and picnicking in beautiful surroundings. Local landmarks such as the nearby beach, lake, and marina provide ample opportunities for relaxation and adventure, making Worton a great spot for nature lovers.
• Georgetown: Nestled within the Chestertown area, Georgetown is a quaint village that beckons visitors with its romantic ambiance and picturesque scenery. This charming destination sees peak travel in the warmer months, particularly from June to August. Georgetown’s boardwalk and golf course offer delightful recreational options, while the nearby national state park and lake serve as perfect backdrops for leisurely strolls and outdoor activities. Whether you’re seeking a peaceful getaway or a romantic escape, Georgetown provides an idyllic setting to unwind and connect with nature.
• Tolchester Beach: A vibrant village within the Chestertown vicinity, Tolchester Beach is renowned for its beachside adventures and outdoor fun. While its traveller arrivals are not significantly seasonal, the peak months from June to August draw visitors eager to enjoy the sun and surf. With attractions like a ski resort and various educational opportunities, Tolchester Beach promises exciting experiences for all. Its beautiful family beach and scenic river make it a fantastic destination for those seeking both relaxation and adventure in a stunning coastal environment.

Things to do in and around Chestertown

Chestertown offers a delightful blend of outdoor activities, family-friendly attractions, and cultural experiences. Visitors can explore educational opportunities, enjoy the local arts centre, and even partake in thrilling motor racing events. This charming town is perfect for those seeking a memorable vacation amidst beautiful surroundings.

Shopping

In Chestertown, you can shop at local boutiques for unique gifts. If you're up for a drive, Queenstown Premium Outlets, 27.4km away, offers a variety of stores. Further afield, Westown, 38.6km from Chestertown, provides a family-friendly shopping experience.

Recreation

At Ripken Stadium, immerse yourself in the energetic atmosphere of live sports events, just a short drive from Chestertown. For golf enthusiasts, Queenstown Harbor Golf Club and Queenstown Harbor Golf Links offer picturesque outdoor settings, where you can enjoy a round of golf amidst beautiful landscapes.

Adventure

At Emmorton Recreation & Tennis Center, 38.6km from Chestertown, experience thrilling recreational activities in a vibrant atmosphere. The Annapolis Sailing School, located 45.1km away, offers exhilarating water sports amidst stunning views. Meanwhile, Tose Family Tennis Center, also 45.1km distant, provides a fantastic setting for tennis enthusiasts.

Nightlife

In Chestertown, the Garfield Center for the Arts offers an enchanting atmosphere with its captivating performances. Just a short drive away, Church Hill Theatre and Everett Theatre provide rich cultural experiences, perfect for a romantic evening filled with entertainment and artistic flair.

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, Maryland, is an excellent destination for outdoor and family vacations, offering a variety of attractions such as urban parks and beaches. Visitors can enjoy the natural beauty and recreational activities available in and around the area, making it perfect for those seeking a beach experience or outdoor adventures. Be sure to explore local points of interest to fully appreciate what Chestertown has to offer.

• Sumner Hall: Immerse yourself in the rich history of Chestertown at Sumner Hall, a museum that showcases the town's cultural heritage. The hall reflects the architectural beauty of the 19th century and hosts various exhibitions that highlight local history and African American culture, making it a captivating stop for history enthusiasts.
• Washington College: Founded in 1782, Washington College is a charming historic university that offers picturesque grounds and stunning architecture. Stroll through its scenic campus to appreciate its cultural significance and the vibrant academic life that thrives here, often hosting events and lectures open to the public.
• Rolphs Wharf Marina: For a taste of adventure, head to Rolphs Wharf Marina. This scenic marina provides opportunities for boating, kayaking, and fishing, set against the backdrop of beautiful water views. It's a perfect spot to relax, enjoy the outdoors, and soak up the natural beauty of the Chesapeake Bay.

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

For travellers heading to Chestertown, Maryland, the major airports include Washington, DC (DCA-Ronald Reagan Washington National) situated 93.3km away and Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) located 51.5km away. Nearby hotel options for DCA include the luxurious Salamander Washington DC and Riggs Washington DC, both within 4.8km, offering convenient access. For those considering BWI, the Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, both 12.9km from the airport, provide excellent accommodation and transport services. Additionally, Baltimore, MD (MTN-Martin State) is just 32.2km away, with hotels like Canopy by Hilton Baltimore Harbor Point and Hyatt Place Baltimore Inner Harbor within a short distance.