Find hotels in Chestertown, MD from Rp952.534

Top reasons to visit Chestertown

• Outdoor Activities: Chestertown offers a variety of outdoor pursuits, including scenic parks and lovely beaches, perfect for relaxation and adventure.
• Cultural Enrichment: The town boasts vibrant arts centres, art walks, and festivals, showcasing local talent and enriching visitors' experiences.
• Historical Charm: Explore unique architectural styles that reflect Chestertown's rich heritage and history.
• Family-Friendly Atmosphere: With numerous attractions and activities, it’s an ideal destination for families seeking fun and relaxation.
• Diverse Accommodation: A range of lodging options, from pet-friendly hotels to welcoming motels, caters to all traveller needs.

Find great hotels in and around Chestertown

Discover a range of charming accommodation options in Chestertown, Maryland, catering to diverse traveller needs. From pet-friendly hotels to welcoming motels, each establishment offers accessible guestrooms and services designed for business travellers and the LGBTQIA community. Whether you're seeking a relaxing getaway or a convenient base for exploration, Chestertown’s lodging choices promise a memorable experience.

• Homewood Suites by Hilton Bel Air: Discover the adventurous spirit at Homewood Suites by Hilton Bel Air, a welcoming 3-star hotel just 33.8km from Chestertown. Ideal for thrill-seekers and the LGBTQIA community, this property offers a plethora of outdoor activities including rock climbing, ziplining, and horse riding nearby. The hotel is pet-friendly, allowing for an inclusive stay with your furry companions. Enjoy spacious suites equipped with modern amenities, a complimentary breakfast, and a range of recreational options to make your stay both exciting and comfortable.
• Holiday Inn Express Annapolis East-Kent Island by IHG: Situated 30.6km from Chestertown, the Holiday Inn Express Annapolis East-Kent Island is perfect for families and business travellers alike. This property boasts an array of outdoor activities such as kayaking, fishing, and hiking. Families will appreciate the thoughtful amenities tailored for children, including free cribs and safety features around the pool. With its modern facilities and convenient location, this hotel ensures a comfortable and enjoyable stay for all guests, whether you're here for work or leisure.
• Driftwood Inn: Nestled in the heart of Chestertown, Driftwood Inn offers a charming motel experience, particularly suited for pet owners. This welcoming property allows pets, ensuring that your furry friends can join in on the holiday fun. With its tranquil setting and easy access to local attractions, Driftwood Inn is an excellent choice for those seeking a laid-back getaway that feels like home. Enjoy the friendly atmosphere and simple comforts that make your stay memorable.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of historical charm and outdoor adventure, making it perfect for family vacations. Visitors can explore the architectural beauty of the region, including the unique styles that reflect its rich heritage. Nearby attractions like the Adirondack region and Baltimore County provide a friendly atmosphere for relaxation and exploration. Whether you're seeking budget-friendly options or a family-friendly environment, Chestertown promises an unforgettable experience for every traveller.

• Worton: Nestled approximately 6.4km from Chestertown, Worton is a charming city that offers a delightful blend of outdoor activities and picturesque scenery. The travel experience here is particularly enjoyable during the peak seasons of April to May and July, when visitors flock to explore its recreational areas and natural beauty. Whether you're hiking through trails, enjoying a day at the beach, or visiting the local marina, Worton is perfect for those seeking a refreshing escape. Its proximity to scenic lakes and beautiful landscapes makes it a great spot for relaxation and exploration.
• Georgetown: Located within the Chestertown area, Georgetown is a quaint village known for its romantic atmosphere and entertaining experiences. Visitors are drawn here mainly between June and August, when the village buzzes with life. The delightful boardwalk, golf course, and private country clubs offer a mix of leisure and social activities. Nature enthusiasts will appreciate the nearby national state park and serene lakes, making Georgetown a perfect destination for couples and families alike seeking both adventure and relaxation in a picturesque setting.
• Tolchester Beach: Just a stone's throw from Chestertown, the village of Tolchester Beach invites families and outdoor lovers to enjoy its sandy shores and vibrant atmosphere. The peak travel months from June to August see visitors indulging in beach activities, while the slightly quieter months of December to February provide a perfect backdrop for peaceful retreats. With attractions such as family-friendly beaches, rivers, and even ski resorts nearby, Tolchester Beach offers a versatile experience for those looking to relax by the water or embrace a bit of adventure.

Things to do in and around Chestertown

Chestertown is an ideal destination for outdoor and family vacations, offering a range of activities such as educational experiences, vibrant arts centres, and motor racing. Visitors can enjoy band tours, art walks, and lively art festivals, as well as explore various art galleries that showcase local talent. This charming town combines cultural enrichment with outdoor enjoyment, making it a delightful spot to explore during your stay.

Shopping

For shopping in Chestertown, visit local boutiques for unique souvenirs. If you're up for a drive, the Queenstown Premium Outlets, 27.4km away, offers a variety of brands, while Westown, 38.6km away, features family-friendly shops and eateries for a delightful experience.

Recreation

Ripken Stadium, located 35.4km from Chestertown, offers vibrant sports events that energise and invigorate. Alternatively, Queenstown Harbor Golf Club and Queenstown Harbor Golf Links, both 27.4km away, provide stunning outdoor golf experiences amidst picturesque landscapes, perfect for relaxation and enjoyment in nature.

Adventure

Experience the thrill at Emmorton Recreation & Tennis Center, located 38.6km from Chestertown, offering a vibrant atmosphere for sports enthusiasts. Head to Annapolis Sailing School, 45.1km away, for exhilarating sailing adventures amidst stunning waters. Additionally, Tose Family Tennis Center, also 45.1km away, promises an energetic tennis experience.

Nightlife

In Chestertown, the Garfield Center for the Arts at the Prince Theatre offers a charming atmosphere with its cultural performances. Nearby, the Church Hill Theatre provides an intimate setting for engaging shows, while the Milburn Stone Theatre, a short drive away, promises romance and entertainment in a delightful environment.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, consider visiting during the cheaper months of January, February, and November. Tuesdays typically offer the best accommodation rates, while Saturdays are the most expensive. Use Expedia’s search tool to filter by budget and preferences, and consider eco-certified hotels for sustainable options. You can also save by booking a package deal that combines flights, hotels, and activities. Finally, take advantage of free activities in the area and use public transport or walk to explore, as Chestertown is compact and walkable.

• 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 preferences, such as your budget, preferred location, and the type of accommodation you desire. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels currently available. To find the most affordable options and offers, arrange 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 ideal destination for outdoor enthusiasts and families seeking a beach holiday. Visitors can explore a variety of attractions including urban parks and scenic beaches, offering ample opportunities for relaxation and recreation. Whether you're looking for a leisurely day by the shore or an adventurous outing in nature, Chestertown provides a delightful experience for all types of travellers.

• Washington College: A historic institution nestled in the heart of Chestertown, Washington College offers a glimpse into American educational heritage. Its charming campus, adorned with beautiful architecture, provides a vibrant cultural atmosphere, making it a perfect spot for leisurely strolls and enriching experiences.
• Rolphs Wharf Marina: Embrace the great outdoors at Rolphs Wharf Marina, where adventure awaits. This scenic marina is ideal for boating, fishing, and enjoying the beach. With picturesque views of the water, it’s a wonderful place for relaxation and excitement alike.
• River Arts Chestertown: Immerse yourself in local creativity at River Arts Chestertown. This arts centre showcases diverse artworks and hosts various cultural events, providing a unique insight into the artistic spirit of the community.

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 major airports. Washington, DC (DCA-Ronald Reagan Washington National), situated 93.3km away, offers luxurious accommodation options such as The Ritz-Carlton, Pentagon City, just 1.6km from the airport. Baltimore, MD (BWI-Baltimore Washington International Thurgood Marshall), located 51.5km from Chestertown, features excellent hotels like The Ivy Hotel, 14.5km from the airport. Additionally, Baltimore, MD (MTN-Martin State) is 32.2km away, with nearby options including the Hampton Inn Baltimore/White Marsh, 6.4km from the airport. Each hotel provides various transportation services to ensure a seamless journey to and from the airports.