Chestertown Hotels from ₹5,176

Top reasons to visit Chestertown

• Historic Charm: Explore the picturesque streets of historic Chestertown, rich in cultural heritage and family-friendly vibes.
• Outdoor Adventures: Enjoy a variety of outdoor activities in beautiful parks and serene landscapes, perfect for nature lovers.
• Local Events: Immerse yourself in the vibrant local community by participating in various events throughout the year.
• Accommodations: Experience a range of comfortable and charming lodging options, including pet-friendly and LGBTQIA-inclusive hotels.
• Relaxing Atmosphere: Unwind in the friendly, tranquil environment that Chestertown offers, ideal for budget-conscious travellers.

Find great hotels near Chestertown

Discover a selection of charming accommodations in Chestertown, Maryland, where comfort meets convenience. Whether you're seeking a pet-friendly hotel, a welcoming environment for LGBTQIA travellers, or suitable options for business trips, Chestertown offers a variety of hotels and motels to cater to your needs. Experience the quaint charm of this historic town while enjoying a memorable stay at one of its inviting establishments.

• Quality Inn & Suites Bel Air I-95 Exit 77A: This budget-friendly hotel caters to business travellers seeking convenience and comfort. Located 34km from Chestertown, it offers essential amenities such as complimentary Wi-Fi, a business centre, and meeting facilities. Guests appreciate the straightforward, no-frills approach of the Quality Inn, which includes spacious rooms designed for relaxation after a long day. The property ensures easy access to nearby restaurants and attractions, making it a suitable base for those on work-related trips.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: With a guest rating of 8.2 out of 10, this pet-friendly hotel is an excellent choice for travellers accompanied by furry companions. Located 34km from Chestertown, it provides amenities such as a complimentary breakfast, fitness centre, and a welcoming atmosphere for pets, with specific policies for dogs and cats. Guests enjoy the comfort of well-appointed rooms and the convenience of nearby dining options, making it a delightful stop for leisure and pet-friendly travel.
• Americas Best Value Inn Edgewood: Another budget-friendly option, Americas Best Value Inn Edgewood is also situated 34km from Chestertown. This hotel is designed for those travelling with pets, offering flexible policies and amenities tailored to ensure a comfortable stay for both guests and their animals. With its straightforward accommodations, including essential services and a convenient location, the inn provides a practical choice for budget-conscious travellers looking to explore the area while enjoying quality time with their pets.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor adventure and historical charm, perfect for a memorable getaway. Wander through the historic streets of Chestertown, where family-friendly vibes abound, or explore the serene landscapes of the Eastern Shore. Nearby, you can enjoy relaxation and friendly atmospheres, making it an ideal destination for budget-conscious travellers seeking both tranquillity and culture. Don't miss the opportunity to experience the peaceful surroundings that define this charming location.

• Worton: Nestled a mere 6km from Chestertown, Worton is a charming city that attracts visitors year-round, particularly from April to May and during the summer months of July. Known for its stunning outdoor scenery, Worton offers a wealth of recreational activities. The area is perfect for those who appreciate nature, with many local landmarks such as beaches, bays, and lakes nearby. Travellers can indulge in various outdoor pursuits, making it an ideal spot for families and nature enthusiasts alike.
• Georgetown: Located conveniently within the Chestertown area, Georgetown is a quaint village that invites visitors with its romantic charm and outdoor activities. This delightful village experiences peak travel between June and August, providing ample opportunities for exploration. With a recreation centre and scenic hiking trails, Georgetown is perfect for those seeking to connect with nature while enjoying some entertainment. The nearby beach, marina, and national state park add to the allure, making it a lovely destination for couples and families looking for a relaxing getaway.
• Tolchester Beach: As a picturesque village near Chestertown, Tolchester Beach remains a hidden gem for those seeking outdoor adventures and beachside relaxation. While visitor numbers are fairly consistent throughout the year, the peak season typically occurs in May and from July to August. Here, travellers can enjoy family-friendly beaches and a marina, alongside activities such as skiing and education. The scenic beauty of Tolchester Beach makes it a perfect destination for those wishing to unwind while soaking in the surrounding natural landscape.

Things to do in Chestertown

Shopping

In the heart of Chestertown, you'll find charming shops like The Bookplate and The Spice & Tea Exchange, ideal for unique gifts. If you're up for a drive, explore the larger selections at the nearby Kent Island Shopping Centre, about 32km away, for more variety.

Recreation

Experience tranquility at the Chester River Health and Wellness Centre, where you can indulge in yoga classes and holistic therapies. For outdoor recreation, explore the scenic paths of the Eastern Shore Land Conservancy, perfect for leisurely walks and birdwatching amidst beautiful landscapes.

Adventure

Explore the scenic Chester River by kayaking or paddleboarding, immersing yourself in the tranquil waters while spotting local wildlife. For a thrilling experience, take a guided fishing charter to try your hand at catching a variety of fish in the rich waters of the Chesapeake Bay.

Nightlife

Chestertown offers a charming nightlife with venues like The Bookplate for a relaxed evening with cocktails and live music. For a vibrant atmosphere, visit The Garfield Centre for the Arts, where you can enjoy cultural performances or exhibits that bring the local scene to life.

Find the best attractions in and around Chestertown

Chestertown offers a delightful blend of outdoor activities and scenic beauty, making it an ideal destination for beach and nature enthusiasts. Visitors can explore parks and urban spaces, perfect for family outings. Additionally, don't miss the opportunity to immerse yourself in the town's rich history by visiting historic Chestertown, which adds a cultural touch to your adventure.

• Historical Society of Kent County Maryland: Immerse yourself in the rich heritage of Kent County at this history museum located in Chestertown. With engaging exhibits and local artefacts, it offers a compelling glimpse into the region's past and cultural legacy.
• Mount Harmon Plantation: Situated 21km from Chestertown, this historic house invites visitors to explore its beautifully preserved grounds and learn about colonial life. The plantation's architecture and gardens reflect the area's deep historical roots.
• Wilmer Park: Located within Chestertown, this urban park provides a delightful space for families to relax and enjoy outdoor activities. With scenic views and recreational facilities, it’s an ideal spot for a leisurely day out amidst nature.

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 through its major airports. Philadelphia International Airport (PHL) is located 101km away, with nearby luxurious hotels like W Philadelphia and The Ritz-Carlton, both approximately 6-11km from the airport. Ronald Reagan Washington National Airport (DCA), situated 93km from Chestertown, offers upscale accommodation at the InterContinental Washington D.C. - The Wharf and Pendry Washington DC - The Wharf, both just 3km away. Lastly, Washington Dulles International Airport (IAD) is 122km away, with excellent hotel options like Hyatt Regency Dulles International Airport and The Westin Washington Dulles Airport, both a mile from the airport.