Find hotels in Chestertown, MD from CA $74

Top reasons to visit Chestertown

• Scenic Chesapeake Bay: Enjoy stunning views and outdoor adventures at the picturesque Chesapeake Bay, perfect for relaxation or exploration.
• Charming Downtown: Stroll through quaint shops and art galleries, immersing yourself in the local culture and history.
• Family-Friendly Activities: Chestertown offers various activities suitable for families, ensuring fun for all ages.
• Outdoor Recreation: Experience a blend of outdoor activities amid the town's natural beauty, from parks to marinas.
• Diverse Accommodations: Find a range of hotels and motels, catering to every traveller's needs and preferences.

Find great hotels in Chestertown

Discover a charming array of hotel accommodations in Chestertown, Maryland, perfect for every traveller. Whether you're seeking budget-friendly options or more comfortable stays, you'll find a variety of 2 to 4-star hotels and motels tailored to your needs. With family-friendly amenities, pet-friendly options, and business services, Chestertown's hotels cater to diverse vacation experiences, ensuring a memorable getaway in this quaint riverside town.

• Quality Inn & Suites Bel Air I-95 Exit 77A: Emphasizing a professional atmosphere, Quality Inn & Suites Bel Air I-95 Exit 77A caters primarily to business travellers seeking comfort and convenience. Situated 33.8km from Chestertown, this hotel boasts essential amenities like a 24-hour business centre and meeting rooms, ensuring a productive stay. Guests appreciate the complimentary breakfast and high-speed internet, making it easy to stay connected. With its focus on providing a seamless business experience, this hotel is an excellent choice for those travelling for work.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: For nature lovers and pet owners, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A offers a welcoming and serene retreat 33.8km from Chestertown. This hotel encourages guests to travel with their furry friends, featuring a pet-friendly policy that accommodates dogs and cats. The property is designed to provide a natural experience, with amenities that promote wellness and relaxation. Guests can enjoy comfortable rooms while taking advantage of the nearby natural attractions, making it an ideal choice for outdoor enthusiasts.
• Best Western Kent Narrows Inn: Situated 32.2km from Chestertown, Best Western Kent Narrows Inn blends business and leisure seamlessly. This hotel caters to both business travellers and pet owners, offering crucial business amenities such as a 24-hour business centre and meeting rooms. With a pet policy that welcomes both dogs and cats, guests can travel with their companions. The combination of professional services and a friendly atmosphere makes this hotel a versatile option for those looking to balance work and leisure during their stay.

Where to stay in Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor adventures and historical charm. Explore the picturesque downtown, where quaint shops and art galleries abound, or venture to the scenic Chesapeake Bay for stunning views. Enjoy family-friendly activities and immerse yourself in the rich history of the area. Whether you seek relaxation or an engaging getaway, Chestertown and its surrounding neighbourhoods promise a welcoming atmosphere filled with friendly locals and memorable experiences.

• Georgetown: Nestled close to Chestertown, Georgetown is a charming village that offers a delightful mix of outdoor adventures and romantic getaways. The travel experience here is best enjoyed during the warmer months, particularly from June to August when visitor numbers peak. The area is home to a variety of recreational options, including educational centres and sports facilities. For nature enthusiasts, the proximity to a national state park offers ample opportunities for hiking and wildlife observation, making Georgetown a perfect spot for those looking to reconnect with nature.
• Tolchester Beach: A picturesque village located near Chestertown, Tolchester Beach is renowned for its scenic coastal beauty and outdoor activities. This destination sees a surge in visitors during the summer months, particularly from June to August, while the colder months bring a slight decline in tourism. The boardwalk is a highlight, offering a leisurely stroll with stunning views, and the nearby marina provides exciting water sports opportunities. The beach itself is perfect for sunbathing and enjoying the tranquil waters, making it an ideal spot for those seeking relaxation and adventure alike.
• Pomona: Situated in proximity to Chestertown, Pomona is a vibrant village that blends culture with outdoor enjoyment. Visitors flock to Pomona during the summer, with peak arrivals from June to August. The area boasts an arts centre and educational venues, which contribute to its cultural appeal. The local beach and marina offer a perfect backdrop for leisurely days by the water or engaging in various water-based activities. The harbour adds to the charm, creating a wonderful environment for exploration and relaxation, making Pomona a must-visit on your vacation itinerary.

Things to do in Chestertown

Chestertown offers a delightful blend of outdoor activities and scenic beauty, making it an ideal vacation spot. Visitors can enjoy educational experiences, explore recreational areas, and stroll along the picturesque boardwalk. Whether you're looking to relax in nature or engage in various activities, Chestertown provides a charming setting for a memorable getaway.

Shopping

In Chestertown, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, visit Queenstown Premium Outlets, 27.4km away, for a variety of brands, or check out Westown, located 38.6km away, offering a mix of family-friendly shops.

Recreation

Ripken Stadium, located 35.4km from Chestertown, offers an energetic atmosphere for sports enthusiasts. For a more tranquil experience, visit Queenstown Harbor Golf Club and Queenstown Harbor Golf Links, both 27.4km away, where you can enjoy scenic outdoor golfing surrounded by picturesque landscapes.

Adventure

Experience the thrill of sailing at Annapolis Sailing School, located 45.1km from Chestertown. Enjoy the excitement of navigating the waters while soaking in the beautiful surroundings. This adventure promises a blend of sport and outdoor fun, perfect for both beginners and seasoned sailors.

Nightlife

Experience a vibrant night in Chestertown at the Garfield Center for the Arts for a cultural performance, or head to Church Hill Theatre for a family-friendly show. For a taste of excitement, venture to Hollywood Casino for a romantic evening filled with gaming and city vibes.

Booking tips and Expedia advantages for Chestertown

Chestertown, Maryland, offers numerous ways for Canadian tourists to save money. Visit free attractions like Washington College, Rolphs Wharf Marina, and Betterton Beach. Plan your trip during budget-friendly months—January to February and November—when accommodation costs are lower, especially on Tuesdays. For better deals, use Expedia's search tool to refine your preferences, apply filters for eco-certified hotels, and consider package deals that combine flights and hotels. By carefully selecting your travel dates and exploring free local activities, you can enjoy a memorable vacation 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 preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the "Eco-certified" filter will show you a selection of sustainable and environmentally-friendly hotels that are currently available. 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.

Find the best attractions in Chestertown

Chestertown, Maryland, is a delightful destination for outdoor enthusiasts and families alike, offering scenic beaches, urban parks, and a charming marina. Visitors can immerse themselves in the natural beauty and enjoy various activities, making it an ideal spot for a memorable beach vacation. Whether you're looking to relax by the water or explore the local parks, Chestertown provides a perfect blend of adventure and tranquility for all types of travellers.

• Washington College: Explore this historic institution located in the heart of Chestertown. With its rich cultural heritage and beautiful campus, Washington College offers a glimpse into American history and education, making it an enriching experience for visitors.
• Rolphs Wharf Marina: Enjoy the scenic beauty and outdoor adventures at Rolphs Wharf Marina. This charming marina provides opportunities for boating, fishing, and relaxing by the beach, perfect for those seeking a mix of adventure and tranquility.
• River Arts Chestertown: Immerse yourself in local creativity at River Arts Chestertown. This arts centre showcases a variety of artworks and hosts engaging events, allowing you to connect with the vibrant artistic community of the area.

Best time to go to Chestertown

Visitor numbers in Chestertown is generally unchanged in popularity throughout the year. The best time to visit Chestertown is dependant 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

Chestertown, Maryland, can be conveniently accessed via several major airports. Washington, DC (DCA-Ronald Reagan Washington National) is located 93.3km away, with nearby hotels like the 5-star InterContinental Washington D.C. - The Wharf, 3.2km from the airport. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is 33.2km away, featuring luxurious options such as the Four Seasons Hotel Baltimore, 12.9km from the airport, which offers various transportation services. Lastly, Baltimore, MD (MTN-Martin State) is 32.2km from Chestertown, with hotels like Canopy by Hilton Baltimore Harbor Point, 16.1km from the airport, ensuring easy access to your travel needs.