Find hotels in Chestertown, MD from Rp1.279.816

Top reasons to visit Chestertown

• Scenic Waterfront: Enjoy leisurely strolls along the picturesque waterfront, taking in the charming views and serene atmosphere.
• Historical Charm: Explore the quaint historic streets and immerse yourself in the rich history of Chestertown.
• Outdoor Adventures: Engage in various outdoor activities, from hiking to nature walks, ideal for families and nature enthusiasts.
• Cultural Experiences: Immerse yourself in local culture through community events and historical attractions.
• Diverse Accommodation: Choose from a variety of welcoming hotels catering to all travellers, ensuring a comfortable stay.

Find great hotels near Chestertown

Discover the charm of Chestertown, Maryland, with a variety of accommodation options tailored to suit every traveller. Whether you're seeking a pet-friendly hotel, a welcoming space for business trips, or an LGBTQIA-friendly environment, Chestertown's hotels offer comfort and convenience for all. Explore our selection of hotels and motels to find the perfect lodging for your memorable stay in this historic town.

• Quality Inn & Suites Bel Air I-95 Exit 77A: This budget-friendly hotel offers a comfortable stay for business travellers, located 34km from Chestertown. The Quality Inn & Suites features spacious rooms equipped with modern amenities, ensuring a productive environment. Guests can enjoy complimentary breakfast, free Wi-Fi, and a well-equipped business centre. Additional amenities include a fitness centre for those wishing to maintain their workout routine during their stay. The property’s convenient location near I-95 provides easy access to the surrounding areas, making it a practical choice for those on business trips.
• Red Roof Inn Aberdeen: Situated 35km from Chestertown, this budget-friendly hotel welcomes guests with pets, making it an appealing choice for animal lovers. The Red Roof Inn Aberdeen allows both cats and dogs, ensuring your furry friends can accompany you on your travels. The hotel offers comfortable accommodation with essential amenities such as free Wi-Fi, flat-screen TVs, and a 24-hour front desk. The surrounding area provides a variety of dining options, and the pet-friendly policy ensures a relaxed atmosphere for both guests and their pets.
• Extended Stay America Suites Baltimore Bel Air Aberdeen: Located 34km from Chestertown, this budget-friendly hotel caters to long-term stays with its suite-style accommodations. Guests can enjoy a fully equipped kitchen in each suite, providing the flexibility to prepare meals during their visit. The property is also pet-friendly, with specific policies in place for furry companions. Guests appreciate amenities such as free Wi-Fi and on-site laundry facilities, making it an ideal choice for those seeking a home-like environment while away. The hotel’s convenient location offers easy access to local attractions and major roadways.

Where to stay in and around Chestertown

Chestertown, Maryland, is a charming destination perfect for outdoor enthusiasts and history buffs alike. Nestled on the Eastern Shore, this picturesque town offers a blend of family-friendly activities and serene landscapes. Explore the historic streets, relax by the waterfront, and immerse yourself in the local culture. Nearby attractions provide a friendly atmosphere, making it an ideal spot for a peaceful getaway filled with exploration and relaxation.

• Worton: Situated a mere 6km from Chestertown, Worton is a charming town that offers a refreshing outdoor experience. With visitor numbers peaking in spring and summer, it's an ideal destination for those seeking scenic beauty and recreational activities. Wander through its picturesque landscapes, enjoy the local beaches and lakes, or take part in educational programmes. Worton caters to nature lovers and families alike, providing ample opportunities for exploration and relaxation amidst its tranquil surroundings.
• Georgetown: Nestled within the Chestertown area, Georgetown is a quaint village that excels in providing a romantic and entertaining atmosphere. The peak visiting season from June to August attracts couples and adventurers alike. Outdoor enthusiasts can explore recreational centres and hiking trails, while the nearby marina and national state park present additional attractions for nature lovers. Georgetown’s charming ambiance makes it a perfect spot for leisurely strolls and enjoying quality time with loved ones.
• Tolchester Beach: Located conveniently close to Chestertown, Tolchester Beach is a delightful village that attracts visitors year-round, particularly in the summer months. Known for its stunning coastal scenery, it is a haven for beachgoers and outdoor enthusiasts. The area offers a variety of activities, including skiing at nearby resorts and educational excursions. Families will appreciate the family-friendly beaches and marinas that make Tolchester Beach an enjoyable destination for all ages, ensuring a memorable holiday experience.

Things to do in Chestertown

Shopping

In the heart of Chestertown, you can explore charming boutiques like The Bookplate for unique gifts and the Chestertown Antique & Flea Market for eclectic finds. If you're up for a drive, head to the nearby Town Mall of Waldorf for a larger shopping experience with familiar brands.

Recreation

Experience the tranquil atmosphere at the Haven Retreat, where you can indulge in yoga sessions and mindfulness workshops. For outdoor enthusiasts, the nearby Chester River offers kayaking and scenic trails for leisurely strolls, perfect for reconnecting with nature.

Adventure

Explore the beautiful Chester River by kayaking or paddleboarding, offering a unique perspective of the area's scenic views. For hiking enthusiasts, the nearby Eastern Neck National Wildlife Refuge provides trails through diverse habitats teeming with wildlife, creating a perfect adventure for nature lovers.

Nightlife

The nightlife in Chestertown offers a charming blend of local pubs and intimate venues. Enjoy live music at The Chester River Yacht & Country Club, or unwind with a craft beer at the Doghouse. Each place reflects the town's warm community spirit and inviting atmosphere.

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 offers a delightful blend of outdoor adventures and scenic beauty, ideal for families and beach enthusiasts. Visitors can explore local parks, enjoy leisurely strolls along the waterfront, and take in the charming historic sites of Chestertown. Don't miss the opportunity to immerse yourself in the local culture while relishing the picturesque landscapes that surround this quaint town.

• Historical Society of Kent County Maryland: Discover the rich heritage of Kent County at this charming museum, where exhibits delve into local history and culture. The society often hosts events and exhibits that celebrate the unique stories of the area, providing a deeper understanding of its past.
• Wilmer Park: This picturesque urban park offers a serene escape with beautiful views of the Chester River. Ideal for family outings, it features walking trails, picnic areas, and playgrounds, making it a perfect spot for relaxation and outdoor activities amidst a vibrant community atmosphere.
• River Arts Chestertown: Immerse yourself in the local arts scene at this vibrant arts centre, showcasing works from regional artists. Visitors can explore galleries, attend workshops, and participate in community art events, enhancing their appreciation for the creative spirit of Chestertown.

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

Accessing Chestertown, Maryland, is convenient via three major airports. Washington, DC (DCA-Ronald Reagan Washington National) is 93km away, with excellent hotels such as the InterContinental Washington D.C. - The Wharf, Pendry Washington DC - The Wharf, and Salamander Washington DC, all within 3km. Washington, DC (IAD-Washington Dulles Intl.) is 122km away, featuring the Hyatt Regency Dulles International Airport, The Westin Washington Dulles Airport, and DoubleTree by Hilton, all closely located. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is the closest, at 51km, with luxury options like Four Seasons Hotel Baltimore, Pendry Baltimore, and The Ivy Hotel, all around 8 to 14km from the airport.