Find hotels in Chestertown, MD from SAR 214

Top reasons to visit Chestertown

• Outdoor Adventures: Chestertown boasts beautiful parks and scenic landscapes perfect for family-friendly outdoor activities.
• Rich History: Explore the charming, historic streets of Chestertown, offering a relaxing and low-crowd experience.
• Local Arts Scene: Visit the local arts center to appreciate the vibrant artistic community and cultural offerings.
• Family-Friendly Atmosphere: Enjoy budget-friendly options and activities tailored for families seeking unique vacation experiences.
• Diverse Accommodations: Choose from a wide range of hotels and motels catering to various traveler needs.

Find great hotels near Chestertown

Discover a variety of hotel accommodations in Chestertown, Maryland, ideal for every type of traveler. Whether you're seeking pet-friendly options, business amenities, or a welcoming atmosphere for LGBTQIA visitors, Chestertown offers a range of hotels and motels to suit your needs. Explore reviews and find the best suites for a comfortable stay in this charming town, making your visit truly memorable.

• Quality Inn & Suites Bel Air I-95 Exit 77A: Experience a perfect blend of comfort and convenience at Quality Inn & Suites Bel Air I-95 Exit 77A, located 33.8km from Chestertown. This hotel caters primarily to business travelers, offering essential amenities such as a well-equipped business center, meeting rooms, and complimentary Wi-Fi. Guests appreciate the spacious rooms designed for relaxation after a busy day, along with a complimentary breakfast to kickstart the morning. With easy access to major highways, it’s an ideal choice for those looking to balance work and leisure.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: If you're seeking a pet-friendly getaway, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A is the perfect destination, situated 33.8km from Chestertown. This welcoming hotel allows pets at no extra charge and provides amenities like a pet policy that includes restrictions for dogs and cats. Guests rave about the comfortable accommodations and the outdoor pool, perfect for unwinding with your furry friends. The hotel also features a complimentary breakfast, ensuring a delightful start to your day.
• Red Roof Inn Aberdeen: Located 35.4km from Chestertown, Red Roof Inn Aberdeen stands out as a welcoming haven for LGBTQIA travelers and their pets. This hotel, affiliated with LGBTQI travel guides, offers a friendly atmosphere with a pet policy that allows dogs and cats, ensuring your companions are welcome. Guests appreciate the modern rooms and convenient amenities, such as free Wi-Fi and on-site parking. With a commitment to inclusivity and comfort, this hotel is an excellent choice for diverse travelers looking for a friendly stay.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a memorable getaway filled with family-friendly activities and rich history. Explore the charming streets of historic Chestertown, where low crowds allow for a relaxing experience. Nearby, the scenic Eastern Shore beckons with its beautiful landscapes and friendly atmosphere. Discover budget-friendly options and enjoy outdoor adventures that make this destination perfect for families seeking a unique vacation experience.

• Worton: Located a mere 6.4km from Chestertown, Worton is a charming city that boasts a delightful mix of outdoor adventures and scenic beauty. With a moderately seasonal influx of travelers, visitors flock to Worton primarily from April to May and during the summer months. Known for its recreational areas, Worton offers ample opportunities for outdoor activities, making it perfect for nature enthusiasts. Local landmarks such as the nearby beach, lake, and marina provide a picturesque backdrop for relaxation and exploration.
• Great Oak Landing: Nestled within the Chestertown area, Great Oak Landing is a quaint village that attracts visitors year-round, with peak travel occurring between June and August. This destination is ideal for couples seeking a romantic getaway, offering outdoor activities and a serene beach atmosphere. Great Oak Landing is well-known for its stunning modern bridge and inviting ski resort, ensuring that there’s something for everyone, whether you prefer lounging by the water or hitting the slopes.
• Church Hill: About 11.3km away from Chestertown, Church Hill is a vibrant city that welcomes travelers with an adventurous spirit. With peak visitation from March to April and September, this area is perfect for families looking for outdoor excitement. Church Hill features various attractions, including nature reserves and golf courses, making it an ideal destination for both relaxation and recreation. The impressive modern bridge adds to the charm, providing a scenic route and a stunning view of the surrounding landscape.

Things to do in and around Chestertown

Chestertown offers a delightful blend of outdoor activities suitable for family vacations, including educational experiences and visits to the local arts center. Visitors can also enjoy the excitement of motor racing, making it a perfect destination for those seeking adventure and culture in one picturesque setting.

Shopping

In Chestertown, you can enjoy local shops and boutiques for unique gifts. If you're up for a drive, visit the Queenstown Premium Outlets, 27.4km away, featuring a variety of brands. Also, check out Paul Reed Smith Guitars and Westown, located 21 and 38.6km away, respectively.

Recreation

At Ripken Stadium, immerse yourself in the energetic atmosphere of live sports events, perfect for sports enthusiasts. Nearby, Queenstown Harbor Golf Club and Queenstown Harbor Golf Links offer stunning outdoor golf experiences, where you can enjoy the serene landscapes while playing a round of golf.

Adventure

Experience the thrill of sailing at Annapolis Sailing School, located 45.1km from Chestertown, where you can enjoy the open water and stunning views. For tennis enthusiasts, Emmorton Recreation & Tennis Center, 38.6km away, offers exciting matches, while Tose Family Tennis Center, also 45.1km away, provides vibrant tennis experiences.

Nightlife

In Chestertown, the Garfield Center for the Arts offers a vibrant atmosphere with captivating performances. Nearby, Church Hill Theatre presents charming productions, while the Avalon Theatre, a bit farther out, enriches the cultural scene, making for an enjoyable night filled with romance and entertainment.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, visit during the cheaper months of January to February or November, and consider staying on a Tuesday for the lowest rates. Avoid Saturdays, which are the most expensive. Use Expedia’s search tool to filter hotels by budget and location, and sort results from lowest to highest price. Consider booking a package deal that combines your hotel, flights, and activities to maximize savings. Look for hotel deals and great rates to ensure you get the best value during your visit.

• 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 preferences such as budget, desired location, and hotel type. To find the best prices and deals, simply 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 deal.

Find the best attractions in Chestertown

Chestertown, Maryland, is an ideal destination for outdoor and family vacations, offering a variety of attractions such as urban parks and beautiful beaches. Visitors can enjoy the scenic landscapes and engage in numerous outdoor activities, making it perfect for a memorable getaway. Whether you're exploring local parks or relaxing by the beach, Chestertown promises a delightful experience for travelers seeking adventure and relaxation.

• Washington College: Nestled in the heart of Chestertown, Washington College is a historic institution steeped in tradition. Visitors can enjoy the beautiful campus, rich culture, and various art and music events that showcase local talent, making it a vibrant hub of intellectual and social activity.
• Rolphs Wharf Marina: This picturesque marina offers outdoor adventure and relaxation. Enjoy scenic views of the Chester River, engage in water sports, or simply unwind on the beach. It's a perfect spot for those seeking both excitement and tranquility by the water.
• River Arts Chestertown: An arts center that celebrates local creativity, River Arts Chestertown features rotating exhibitions, workshops, and community events. Experience the rich cultural vibe as you explore unique artworks and engage with local artists.

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

To reach Chestertown, Maryland, you can fly into several major airports. Washington, DC (DCA-Ronald Reagan Washington National) is 93.3km away, with nearby luxurious hotels such as Salamander Washington DC and Riggs Washington DC, both offering easy access to the airport. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is closer at 51.5km, featuring top hotels like Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, which provide convenient transportation options. Additionally, Baltimore, MD (MTN-Martin State) is 32.2km from Chestertown, with options such as Canopy by Hilton Baltimore Harbor Point and Hyatt Place Baltimore Inner Harbor, ensuring accessible travel from the airport.