Find hotels in Chestertown, MD from $58

Top reasons to visit Chestertown

• Scenic Outdoor Activities: Chestertown offers a range of outdoor adventures, including beautiful parks and marinas, perfect for families and nature lovers.
• Charming Historic District: Explore the quaint streets lined with historic buildings that showcase the town's rich heritage.
• Relaxing Chesapeake Bay Atmosphere: Enjoy the serene environment around the bay, ideal for unwinding and taking in the views.
• Variety of Accommodations: Find a wide range of hotels and motels catering to all travelers, including pet-friendly and budget options.
• Local Shops and Eateries: Experience the delightful local cuisine and unique shops that reflect the town's character.

Find great hotels near Chestertown

Discover the charm of Chestertown, Maryland, with a variety of hotel accommodations designed to meet the needs of every traveler. From pet-friendly options to business-friendly amenities, Chestertown hotels offer a welcoming atmosphere for all, including LGBTQIA travelers. Whether you're seeking a cozy motel or a budget-friendly hotel, you'll find the perfect place to relax and explore this picturesque town.

• Quality Inn & Suites Bel Air I-95 Exit 77A: Quality Inn & Suites Bel Air I-95 Exit 77A is a budget-friendly hotel located 21 miles from Chestertown, ideal for business travelers seeking comfort and convenience. With amenities designed for a productive stay, guests can enjoy free Wi-Fi, a business center, and meeting facilities. The hotel also features a complimentary breakfast to kick-start your day. Its proximity to I-95 ensures easy access to local attractions, making it a practical choice for those on the go.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A is a pet-friendly budget hotel with a guest rating of 8.2, situated 21 miles from Chestertown. This welcoming property allows pets, making it an excellent choice for travelers who wish to bring their furry friends along. Guests can enjoy spacious rooms, a complimentary breakfast, and an inviting outdoor pool. The hotel's friendly atmosphere and convenient amenities ensure a pleasant stay for both you and your pets.
• Red Roof Inn Aberdeen: Red Roof Inn Aberdeen is another budget-friendly option, located 22 miles from Chestertown, known for its pet-friendly policies. This hotel welcomes dogs and cats, making it an ideal choice for pet owners. The property offers comfortable accommodations with essential amenities, including free Wi-Fi and a complimentary coffee service. Guests appreciate the convenient location near local attractions, providing a perfect balance of comfort and accessibility during your stay.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of history and scenic beauty perfect for outdoor enthusiasts and families alike. Explore the charming historic district, enjoy the tranquil atmosphere around the Chesapeake Bay, and unwind at Emmorton Recreation. Nearby towns provide friendly vibes and budget-friendly options, making it an ideal destination for a relaxing getaway. Whether you're seeking adventure or a peaceful retreat, Chestertown and its surroundings promise an unforgettable experience.

• Worton: Located a mere 4 miles from Chestertown, Worton is a charming small town that attracts visitors year-round, with peak seasons in April to May and July. Known for its stunning outdoor scenery, Worton is perfect for travelers seeking an active experience. Enjoy recreational areas and educational venues that engage both the mind and body. The nearby beaches, bay, and lakes offer opportunities for relaxation and exploration, making Worton a delightful stop for nature enthusiasts.
• Georgetown: Nestled close to Chestertown, Georgetown is a picturesque village that provides a romantic and entertaining atmosphere. With peak visitor numbers from June to August, this area is ideal for outdoor lovers. Engage in activities at the recreation center or explore scenic hiking trails that showcase the beauty of the region. Local attractions, including a marina and stadium, invite visitors to partake in leisurely activities or catch an exciting event, ensuring that Georgetown has something for everyone.
• Pomona: This welcoming village, situated near Chestertown, sees consistent visitor traffic throughout the year, with the highest numbers during the summer months of June to August. Pomona is an excellent destination for families looking for a beach getaway. With access to shopping centers, malls, and golf courses, there are plenty of activities to enjoy. The nearby urban parks and beaches provide ample opportunities for outdoor fun and relaxation, making Pomona a fantastic spot for a family-friendly vacation.

Things to do in Chestertown

Chestertown, Maryland, offers a perfect blend of outdoor activities and scenic beauty, making it an ideal vacation spot. Visitors can explore various recreational areas, engage in motor racing, and enjoy educational attractions. With a range of entertainment options available, including charming eateries and local shops, Chestertown provides a delightful experience for those looking to unwind in a picturesque setting.

Shopping

In Chestertown, you can explore local shops like The Bookplate for unique gifts and The Kitchen at the Imperial for kitchenware. If you're up for a drive, head to the nearby Easton Marketplace, which features a variety of stores, including home décor and clothing boutiques.

Recreation

The Chestertown Wellness Center offers yoga classes with calming views and meditation sessions to rejuvenate your spirit. For outdoor enthusiasts, the Chester River is perfect for kayaking and paddleboarding, while nearby parks provide scenic trails for hiking and nature walks, ensuring a refreshing retreat for your mind and body.

Adventure

In Chestertown, explore the scenic Chester River by kayaking or paddleboarding, offering a thrilling way to appreciate the beautiful surroundings. For adrenaline seekers, the nearby Eastern Shore boasts hiking trails that lead to breathtaking views, perfect for an adventurous day outdoors.

Nightlife

In Chestertown, the nightlife is cozy and inviting. The Chester River Yacht & Country Club offers lovely views and social gatherings, while local pubs like The Fish Whistle provide a relaxed atmosphere with live music. Enjoy a laid-back evening filled with good company and local brews.

Booking tips and Expedia advantages for Chestertown

• 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: Expedia's search tool lets you set your budget and choose your ideal location, among other preferences. You can easily sort your results by price, allowing you to view the most affordable hotels first. Additionally, you can refine your search by hotel type; for instance, selecting the Eco-certified filter will display sustainable and environmentally friendly hotels that you can book.
• Consider bundling your trip: You can save money by combining your Chestertown hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in Chestertown

Chestertown, Maryland, offers a perfect blend of outdoor adventures and scenic beauty, making it an ideal vacation spot for families and beach lovers. Visitors can explore a variety of attractions, including urban parks, traditional parks, and marinas, all designed to enhance the outdoor experience. Whether you're looking to relax by the water or enjoy nature, Chestertown has something for everyone to enjoy.

• Historical Society of Kent County Maryland: Discover the rich history of the region at this engaging museum. The Society offers insights into local culture and heritage through fascinating exhibits and artifacts, making it a must-visit for history enthusiasts.
• Wilmer Park: This urban park is perfect for families and outdoor lovers alike. Enjoy lovely walking trails, playgrounds, and picnic areas while taking in beautiful views of the Chester River. It's an ideal spot for relaxation and recreation.
• River Arts Chestertown: Immerse yourself in the local art scene at this vibrant arts center. Featuring rotating exhibits and workshops, River Arts promotes community engagement and showcases the talents of regional artists, making it a cultural hub.

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

Traveling to Chestertown, Maryland, is convenient with several major airports nearby. Philadelphia International Airport (PHL) is 63 miles away, with excellent hotel options like the W Philadelphia and The Rittenhouse, both around 6 miles from the airport. Ronald Reagan Washington National Airport (DCA) is 58 miles away, offering luxurious accommodations such as the InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both just 2 miles from the airport. Lastly, Washington Dulles International Airport (IAD) is 76 miles from Chestertown, with nearby hotels like The Westin and Hyatt Regency, both 1 mile away, providing easy access to the airport.