Chestertown hotels from HK$444

Top reasons to visit Chestertown

• Beautiful Outdoor Spaces: Chestertown boasts numerous urban parks and scenic areas ideal for family outings and nature lovers.
• Rich Historical Charm: The town's architecture showcases its heritage, making it a delight for history enthusiasts.
• Vibrant Arts Scene: Visitors can engage with local culture through art walks, festivals, and charming galleries.
• Family-Friendly Activities: A variety of attractions cater to families, ensuring a fun and relaxing experience.
• Diverse Accommodation Options: Chestertown offers a range of lodgings, including pet-friendly and LGBTQIA-friendly options.

Find great hotels near Chestertown

Chestertown, Maryland, offers a delightful array of accommodation options, including hotels and motels that cater to diverse traveller needs. Whether you're seeking pet-friendly lodgings, accessible guestrooms, or facilities that embrace an LGBTQIA-friendly atmosphere, you'll find suitable choices here. With its charming surroundings and welcoming services, Chestertown promises a memorable stay for both leisure and business travellers alike.

• Quality Inn & Suites Bel Air I-95 Exit 77A: Positioned 33.8km from Chestertown, the Quality Inn & Suites Bel Air I-95 Exit 77A offers a professional atmosphere tailored for business travellers. This hotel features well-appointed rooms equipped with modern amenities, including complimentary Wi-Fi, a business centre, and conference facilities, ensuring that your work needs are met while away from home. Guests appreciate the hotel's efficient service and convenient location near major transport links.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: Situated 33.8km from Chestertown, La Quinta Inn & Suites welcomes guests with its pet-friendly policy, making it an ideal choice for those travelling with furry companions. This hotel offers comfortable accommodations with amenities such as free breakfast, an outdoor pool, and spacious rooms. The pet policy is accommodating, allowing dogs and cats, which ensures that your pets can enjoy the holiday as well. Guests often highlight the friendly atmosphere and convenience of nearby dining options.
• Red Roof Inn Aberdeen: Located 35.4km away from Chestertown, Red Roof Inn Aberdeen is a welcoming establishment known for its inclusive environment, catering to pet owners and LGBTQIA travellers alike. This hotel offers a variety of room types, many of which allow pets, ensuring that everyone feels at home. Amenities include free Wi-Fi, a pet-friendly policy with minimal fees, and a warm, inviting atmosphere. Guests commend the hotel for its accommodating staff and comfortable lodgings, making it a great choice for a diverse range of visitors.

Where to stay near Chestertown

Chestertown, Maryland, offers a delightful blend of historical charm and family-friendly activities. Explore the architectural beauty of the town, which reflects its rich heritage, and venture into nearby areas like Baltimore County for a relaxing atmosphere filled with friendly locals. The Adirondack region is also within reach, providing stunning outdoor experiences for all ages. Whether you're seeking budget-friendly options or a historical escape, Chestertown promises a memorable vacation.

• Betterton: Nestled approximately 16.1km from Chestertown, Betterton is a charming coastal town that offers a delightful beach experience. Known for its scenic beauty and outdoor activities, this popular destination attracts visitors particularly during the summer months from June to August. The town features a lovely boardwalk and recreational areas where families can enjoy quality time together. Highlights include the family-friendly beach and marina, making it an ideal spot for those seeking relaxation and vibrant outdoor fun.
• Edgewood: Located around 29.0km from Chestertown, Edgewood is a vibrant city with a mix of family-friendly attractions and business amenities. The town sees consistent visitor traffic throughout the year, peaking in spring and early summer. Edgewood is perfect for those looking for a city-themed experience, with plenty of education options and shopping centres to explore. Local highlights include a prominent sports facility and a historic college, providing a glimpse into the area's rich heritage and community spirit.
• Queenstown: Situated roughly 25.7km from Chestertown, Queenstown is a lively town perfect for families and outdoor enthusiasts alike. With visitor numbers peaking during the summer months, the town offers a plethora of activities such as golfing and shopping. Queenstown's proximity to beautiful beaches and a picturesque lighthouse enhances its appeal, making it a great destination for those looking to combine relaxation and recreation. The town is ideal for family outings, ensuring fun for all ages.

Things to do in and around Chestertown

Chestertown, Maryland, is an ideal destination for outdoor and family vacations, offering a variety of activities. Visitors can explore educational opportunities, enjoy the local arts scene through band tours, art walks, and festivals, or visit charming art galleries. With its vibrant cultural offerings, Chestertown promises a delightful experience for all who venture there.

Shopping

In Chestertown, you can explore local boutiques for unique gifts. If you're up for a drive, visit Queenstown Premium Outlets, 27.4km away, for a variety of brands. Further afield, Westown, 38.6km away, offers family-friendly shopping experiences in a vibrant atmosphere.

Recreation

Ripken Stadium, located 35.4km from Chestertown, offers an energetic atmosphere for sports enthusiasts. Alternatively, Queenstown Harbor Golf Club and Queenstown Harbor Golf Links, both 27.4km away, provide picturesque outdoor settings for golf, perfect for relaxation and enjoying nature's beauty while engaging in recreational activities.

Adventure

Experience the thrill of sailing at Annapolis Sailing School, located 45.1km from Chestertown, where you can embrace the outdoor adventure vibes on the water. Alternatively, enjoy a variety of activities at Emmorton Recreation & Tennis Center or Tose Family Tennis Center, both 24 and 45.1km away respectively.

Nightlife

In Chestertown, the Garfield Center for the Arts offers a delightful mix of romance and culture, perfect for an enchanting evening. Just a short drive away, the Church Hill Theatre presents captivating performances in a charming setting, while the Avalon Theatre promises an unforgettable experience with its rich entertainment offerings.

Booking tips and Expedia advantages for Chestertown

To save money during your visit to Chestertown, consider travelling in the cheaper months of January, February, and November, with Tuesday being the least expensive day to stay. Take advantage of Expedia's search tool to find budget-friendly accommodation and combine your hotel, flights, and activities for additional savings. For transport, utilise public buses or explore the town on foot, as Chestertown is pedestrian-friendly. Lastly, look for free activities such as local parks and events to further enhance your experience without overspending.

• 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 choices based on your budget, desired location, and preferred type of accommodation. To discover the most economical prices and offers, arrange the price filter from lowest to highest.
• Consider bundling your trip: You can reduce your expenses by combining your hotel reservation in Chestertown with your flights and activities through an Expedia package.

Find the best attractions in and around Chestertown

Chestertown, Maryland, is an ideal destination for outdoor and family vacations, boasting a variety of attractions such as urban parks and beautiful beaches. Visitors can explore numerous points of interest that cater to those seeking enjoyable outdoor experiences, making it a perfect spot for families looking to unwind and connect with nature.

• Crumpton Auction: Experience the lively atmosphere of Crumpton Auction, a family-friendly attraction located in Chestertown. This vibrant market features a diverse array of goods, from antiques to local crafts, making it a unique spot to find treasures while enjoying a day out.
• Rock Hall Harbor: Just 17.7km from Chestertown, Rock Hall Harbor offers stunning beach views and picturesque scenery. Perfect for relaxing by the water, you can enjoy boating, fishing, or simply soaking in the natural beauty of the area.
• Eastern Neck National Wildlife Refuge: Located 25.7km away, this reserve is an ideal destination for families and wildlife enthusiasts. Explore its tranquil trails and observe diverse bird species while enjoying a budget-friendly day immersed in nature.

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

Chestertown, Maryland, is conveniently accessible via several airports. Washington, DC (DCA-Ronald Reagan Washington National) is situated 93.3km away, with luxurious hotel options such as Salamander Washington DC, Riggs Washington DC, and Pendry Washington DC - The Wharf, all within 4.8km of the airport. Alternatively, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is only 51.5km from Chestertown, featuring splendid hotels like Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, both 12.9km from the airport. For a closer option, Baltimore, MD (MTN-Martin State) is 32.2km away, with hotels like Canopy by Hilton Baltimore Harbour Point and Hyatt Place Baltimore Inner Harbour located 16.1km from the airport.