Find hotels in Chestertown, MD from $59

Top reasons to visit Chestertown

• Scenic Outdoor Adventures: Chestertown offers stunning natural beauty, perfect for hiking, biking, and exploring nearby parks.
• Historic Charm: Discover the rich history of Chestertown through its quaint streets and well-preserved architecture.
• Vibrant Local Art Scene: Experience the artistic spirit of the community with galleries and local events celebrating creativity.
• Family-Friendly Atmosphere: Enjoy a welcoming environment that caters to families, with activities for all ages.
• Diverse Accommodations: Choose from a range of hotels and guesthouses that fit every traveler's budget and needs.

Find great hotels in Chestertown

Discover the charm of Chestertown, Maryland, with a diverse selection of hotels and accommodations to suit every type of traveler. From budget-friendly options to luxurious stays, you'll find everything from cozy guesthouses to well-appointed suites. Whether you're seeking a family getaway, a pet-friendly environment, or a business-friendly atmosphere, Chestertown's hotels cater to all your needs for a memorable vacation experience.

• Historic Inns of Annapolis: Nestled in a charming national historic building, Historic Inns of Annapolis offers a unique blend of history and adventure for travelers seeking an enriching vacation experience. Located 28 miles from Chestertown, this 3.5-star hotel provides an array of adventure sports and recreation activities both onsite and nearby, including scooter rentals, waterskiing, boat tours, sailing, and bicycle rentals. Families will appreciate the child-friendly amenities, including free cribs and services tailored for children, making it a perfect choice for a family getaway.
• La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Positioned 24 miles from Chestertown, La Quinta Inn & Suites is an ideal choice for families and business travelers alike. This hotel offers a welcoming atmosphere with amenities designed for both leisure and work, including a business center and a strategic location in a business district. Pet lovers will feel right at home, as this property welcomes pets with specific guidelines. Families can also benefit from child-friendly amenities such as free cribs, ensuring a comfortable stay for all.
• Graduate by Hilton Annapolis: Located 28 miles from Chestertown, Graduate by Hilton Annapolis combines modern comforts with a pet-friendly atmosphere, making it a great choice for both business travelers and those traveling with furry companions. This upscale 4-star hotel features essential business amenities such as meeting rooms and conference space, catering to the needs of professionals. Guests can enjoy the convenience of having pets permitted on the property, complete with food and water bowls, ensuring a cozy experience for both guests and their four-legged friends.

Discover the best areas to stay in Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor adventure and historical charm. Explore the scenic beauty of the Eastern Shore, with its family-friendly atmosphere and vibrant local art scene. Discover the quaint streets of Chestertown's center, where friendly locals and budget-friendly options await. Venture into surrounding areas for more experiences that highlight the rich history and community spirit of this picturesque region. Your vacation in Chestertown promises unforgettable memories and a warm welcome.

• Annapolis: Nestled 28 miles from Chestertown, Annapolis is a vibrant city famous for its rich maritime history and beautiful waterfront. Visitors flock to this charming destination year-round, with peak arrivals from May to July. Families, outdoor enthusiasts, and city explorers will find plenty to enjoy here. Popular activities include shopping at local malls, enjoying educational tours, and exploring the historic academy. Don't miss the stunning local landmarks, such as the picturesque beaches and serene lakes, which offer perfect spots for relaxation and recreation.
• Worton: Just 4 miles from Chestertown, Worton is a quaint town that offers a peaceful escape with a focus on outdoor activities and stunning scenery. The town experiences a moderately seasonal influx of travelers, peaking in April to May and July. Visitors can explore recreational areas, engage in educational opportunities, and unwind at nearby beaches and the national state park. The local lakes provide a beautiful backdrop for picnics and leisurely walks, making Worton a great spot for nature lovers and those seeking tranquility.
• Georgetown: Positioned within the Chestertown area, Georgetown attracts visitors looking for outdoor adventures and scenic experiences. With a moderate seasonal flow of tourists peaking from June to August, this vibrant city offers education and recreation, with motor racing being a popular highlight. The local stadium and national state park are must-visit attractions that promise excitement and exploration. Whether you’re hiking through the park or cheering at a sports event, Georgetown offers a dynamic blend of adventure and relaxation for all types of travelers.

Things to do in Chestertown

Chestertown, Maryland, is perfect for outdoor enthusiasts and adventure seekers, offering a range of activities. Visitors can explore scenic boardwalks, enjoy educational experiences, and relax in recreational areas. For a memorable trip, consider local tips and highlights to make the most of your travels in this charming town.

Food and drinks

For a delightful culinary experience in Chestertown, visit Milano's Pizza for delicious pizza options. For a unique local drink, explore Cassinelli Winery and Vineyards, Crow Farm and Vineyard, or Tilmon's Island Winery, all offering charming atmospheres perfect for a romantic outing or a fun night out.

Shopping

In Chestertown, you'll find charming local shops and boutiques perfect for unique gifts and souvenirs. If you're up for a drive, visit the Queenstown Premium Outlets, located 17 miles away, offering a variety of brands and entertainment options for a fun shopping day.

Recreation

At Queenstown Harbor Golf Club, enjoy a round of golf amidst beautiful landscapes just 17 miles from Chestertown, embracing the outdoors and sportsmanship. Similarly, Queenstown Harbor Golf Links offers an inviting atmosphere for golf enthusiasts, while Rocky Point Golf Course, located 19 miles away, provides a vibrant outdoor experience.

Nightlife

Experience the vibrant nightlife in Chestertown at the Garfield Center for the Arts, where culture and entertainment come alive. For a slightly more intimate setting, the Church Hill Theatre offers a charming atmosphere just 7 miles away, perfect for a romantic night out with family or friends.

Booking tips and Expedia advantages for Chestertown

For a budget-friendly visit to Chestertown, Maryland, take advantage of free activities like Washington College, Rolphs Wharf Marina, and Betterton Beach. The cheapest months to visit are December to February, while May to June and September see higher prices. Use Expedia to find affordable hotels by filtering options and arranging results by price. Consider booking a package deal to combine flights and accommodation for extra savings. Joining Expedia's One Key membership can provide exclusive discounts and OneKeyCash for future stays. Don't miss out on current hotel deals for Chestertown!

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chestertown are December to February, where the prices are slightly lower. This is in comparison to May to June and September, where prices are slightly higher.
• Find cheap hotels on Expedia: Expedia’s search tool lets you specify your budget, desired location, and additional preferences. You can arrange the search results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you have the option to refine your search by hotel type. For instance, selecting the "Eco-certified" filter will showcase sustainable and environmentally friendly hotels that are available for booking.
• 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.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in Chestertown

Chestertown, Maryland, is an ideal destination for outdoor enthusiasts, offering stunning scenery and adventurous activities. Visitors can explore the historic town and its rich culture while enjoying attractions like nearby national and state parks, beaches, and marinas. Don't miss the chance to experience the charm of historic Chestertown and the vibrant local community, making it a perfect getaway for those seeking both relaxation and adventure.

• Washington College: As one of the oldest institutions of higher education in the United States, Washington College offers a unique blend of history and culture. You can stroll through its picturesque campus, admire the historic buildings, and learn about its significant role in American education.
• Rolphs Wharf Marina: If you're seeking adventure, Rolphs Wharf Marina is the perfect spot! Enjoy outdoor activities like kayaking, paddleboarding, or simply relaxing by the waterfront. The marina’s scenic views and beach vibes create an idyllic atmosphere for nature lovers.
• River Arts Chestertown: Immerse yourself in the local arts scene at River Arts Chestertown. This vibrant arts center showcases local talent through exhibits, workshops, and events, making it a great place to appreciate and engage with the creative community.

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	Slightly High
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	Average
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	Slightly High
October	59.2°F (15.1°C)	Light Rain	Mostly Sunny	Average	Average
November	47.3°F (8.5°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	40.1°F (4.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

The nearest major airports for your trip to Chestertown

When planning your visit to Chestertown, Maryland, you can conveniently fly into several major airports. Baltimore Washington International (BWI) is located 32 miles away and offers luxurious hotel options like the Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, both 8 miles from the airport with shuttle services available. Ronald Reagan Washington National Airport (DCA) is 58 miles from Chestertown, with upscale hotels such as Salamander Washington DC and InterContinental Washington D.C. - The Wharf just 2 miles away. Additionally, Martin State Airport (MTN) is 20 miles away, with nearby accommodations like Canopy by Hilton Baltimore Harbor Point and Hyatt Place Baltimore Inner Harbor.