Find hotels in Chestertown, MD from NT$1,619

Top reasons to visit Chestertown

• Historic Charm: Stroll through the quaint streets of historic Chestertown, filled with unique shops and local culture.
• Outdoor Adventures: Enjoy charming urban parks and nearby serene beaches, perfect for relaxation and family outings.
• Vibrant Arts Scene: Experience local art and cultural events at the town's vibrant arts center.
• Family-Friendly Activities: Engage in various activities suitable for all ages, ensuring a memorable vacation.
• Welcoming Accommodations: Discover a range of hotels and motels catering to diverse travelers' needs.

Find great hotels near Chestertown

Discover a charming array of hotel accommodations in Chestertown, Maryland, perfect for every type of traveler. Whether you're seeking pet-friendly options, convenient business travel amenities, or an LGBTQIA welcoming environment, Chestertown has something for everyone. With a selection of hotels and motels that cater to various needs, you can find the ideal place to unwind while exploring the historic beauty of this quaint town.

• Quality Inn & Suites Bel Air I-95 Exit 77A: The Quality Inn & Suites Bel Air I-95 Exit 77A offers a professional atmosphere perfect for business travelers. Located 33.8km from Chestertown, this hotel provides a comfortable and convenient stay with amenities tailored for work and relaxation. Guests can enjoy complimentary Wi-Fi, a well-equipped business center, and meeting facilities. The spacious rooms feature ergonomic workstations, ensuring productivity while on the road. Additionally, the hotel serves a complimentary breakfast to kickstart your day, making it an ideal choice for those combining business with leisure.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: Situated 33.8km from Chestertown, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A is a welcoming retreat for travelers with pets. The hotel embraces a pet-friendly policy, allowing dogs and cats, ensuring that your furry companions can join you on your vacation. Guests can enjoy modern amenities, including a fitness center, free breakfast, and comfortable rooms designed for relaxation. The hotel’s convenient location near major highways makes it an excellent stop for families and pet lovers seeking adventure in the area.
• Red Roof Inn Aberdeen: Located 35.4km from Chestertown, Red Roof Inn Aberdeen is a vibrant option for travelers looking for a pet-friendly and LGBTQIA-friendly environment. This hotel stands out for its inclusivity and welcoming atmosphere. Guests can enjoy a range of amenities, including free Wi-Fi, a 24-hour front desk, and a pet-friendly policy with variable fees for pets. The hotel also provides easy access to nearby attractions, making it a great choice for those seeking both comfort and community during their stay.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of history and family-friendly activities. Explore the charming streets of historic Chestertown, where you can soak in the local culture and visit quaint shops. Just a short drive away, the picturesque Eastern Shore beckons with its low crowds and serene beaches. Enjoy memorable getaways filled with relaxation and friendly people, making Chestertown a perfect destination for outdoor adventures and quality time with loved ones.

• Worton: Nestled a mere 6.4km from Chestertown, Worton is a charming city that draws visitors for its stunning outdoor scenery and recreational opportunities. The peak travel season from April to May and July highlights the area's appeal as a perfect getaway for nature enthusiasts. Visitors can enjoy a variety of activities, including exploring the local beaches, lakes, and marinas. Worton's inviting landscape is ideal for those seeking a relaxing outdoor experience, making it a great spot for picnics, hiking, and water sports.
• Georgetown: Located within the Chestertown area, Georgetown is a picturesque village known for its romantic ambiance and beautiful scenery. The village sees a spike in visitors from June to August, as travelers flock to its scenic boardwalk, country private club, and golf course. With attractions like serene lakes and the nearby national state park, Georgetown offers a perfect blend of relaxation and outdoor adventure. Whether you're enjoying a leisurely stroll or participating in recreational activities, Georgetown is a delightful destination for couples and families alike.
• Tolchester Beach: Tolchester Beach is a vibrant village that promises an adventurous experience year-round. Though visitor numbers peak in the summer months of June to August, the allure of its beaches and outdoor activities keeps travelers coming back. With attractions such as family-friendly beaches and river access, Tolchester Beach is perfect for those who love adventure and fun in the sun. The area is also known for its educational opportunities and nearby ski resorts, making it a versatile destination for all types of travelers.

Things to do in and around Chestertown

Chestertown, Maryland, is an ideal destination for outdoor enthusiasts and family vacations. Visitors can explore local educational opportunities, enjoy the vibrant arts center, and experience the thrill of motor racing. With its charming atmosphere and a variety of activities, Chestertown promises an engaging getaway for tourists looking to unwind and create lasting memories.

Shopping

For a delightful shopping experience in Chestertown, visit local boutiques or head to Queenstown Premium Outlets, located 27.4km away, for a variety of stores. If you're up for a drive, check out Paul Reed Smith Guitars and Westown, 21 and 38.6km away, respectively, for unique finds.

Recreation

Ripken Stadium offers an energetic atmosphere for sports enthusiasts, perfect for enjoying live games and community events. Meanwhile, the scenic Queenstown Harbor Golf Club and Queenstown Harbor Golf Links provide challenging courses surrounded by picturesque landscapes, ideal for golfers seeking both relaxation and outdoor adventure.

Adventure

At Annapolis Sailing School, embark on an exhilarating sailing adventure on the Chesapeake Bay, located 45.1km from Chestertown. Emmorton Recreation & Tennis Center, 38.6km away, offers various sports activities amidst an adventurous atmosphere. Meanwhile, Tose Family Tennis Center, also 45.1km distant, invites tennis enthusiasts to enjoy its vibrant environment.

Nightlife

Experience vibrant nightlife at the Garfield Center for the Arts, showcasing local talent in a charming setting. For an enchanting evening, visit the Church Hill Theatre, just 11.3km away, or the Avalon Theatre, 49.9km from Chestertown, both offering captivating performances and cultural experiences.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, plan your visit between January to February or November for the lowest rates. Tuesdays offer the cheapest hotel stays, while Saturdays tend to be the most expensive. Use Expedia’s search tool to find budget-friendly accommodation by sorting options from lowest to highest price. Consider booking a package that combines your hotel, flights, and activities for additional savings. Explore the town on foot to avoid transportation costs, and take advantage of free local attractions to enhance your experience without breaking the bank.

• 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: Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred hotel type. To find the best prices and deals available, 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 vacation spot for families and outdoor enthusiasts. Visitors can enjoy charming urban parks and beautiful beaches, making it an ideal destination for relaxing and exploring. Whether you're looking to soak up the sun or engage in family-friendly activities, Chestertown has something for everyone. Don't miss out on local attractions and experiences that showcase the area's natural beauty and vibrant community.

• Washington College: As one of the oldest institutions of higher education in the United States, Washington College offers a captivating blend of history and culture. Stroll through its beautiful campus, admire the historic architecture, and immerse yourself in the vibrant academic atmosphere.
• Rolphs Wharf Marina: This scenic marina is perfect for adventure seekers and outdoor enthusiasts. Enjoy activities like kayaking, fishing, or simply relaxing by the water while taking in the stunning views of the Chester River. The beach vibes create a perfect escape for nature lovers.
• River Arts Chestertown: Experience local creativity at this arts center, showcasing the work of talented artists. Participate in workshops or browse the galleries to discover unique art pieces, all while enjoying the rich cultural ambiance of Chestertown.

Best time to go to Chestertown

The best time to visit Chestertown is dependent 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	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 can fly into several major airports. Washington, DC (DCA-Ronald Reagan Washington National) is located 93.3km away, with nearby 5-star options like Salamander Washington DC and Riggs Washington DC, both offering convenient access to the airport. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is closer at 51.5km, featuring luxurious hotels such as Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, which provide airport transportation services. Lastly, Baltimore, MD (MTN-Martin State) is only 32.2km away, with accommodations like Canopy by Hilton Baltimore Harbor Point and Hyatt Place Baltimore Inner Harbor, ensuring easy access to your flight.