Chestertown Hotels from S$81

Top reasons to visit Chestertown

• Historic Charm: Stroll through the quaint streets of historic Chestertown, immersing yourself in its rich heritage and warm community atmosphere.
• Outdoor Adventures: Enjoy a variety of outdoor activities amidst the stunning landscapes of the Eastern Shore, perfect for nature enthusiasts.
• Diverse Accommodation: Find a range of delightful lodging options, from pet-friendly hotels to welcoming spaces for LGBTQIA travellers.
• Family-Friendly Attractions: Chestertown offers numerous family-friendly attractions, ensuring enjoyment for visitors of all ages.
• Scenic Beauty: Revel in the picturesque surroundings, ideal for relaxation or adventure amidst nature's tranquillity.

Find great hotels near Chestertown

Explore an array of delightful accommodation options in Chestertown, Maryland, where you can find both hotels and motels tailored to suit your needs. Whether you're seeking a pet-friendly environment, a welcoming space for LGBTQIA travellers, or facilities for business trips, Chestertown has something for everyone. Enjoy a charming escape in this picturesque town, with hotels that cater to both leisure and work-related stays.

• Quality Inn & Suites Bel Air I-95 Exit 77A: Located 33.8km from Chestertown, the Quality Inn & Suites Bel Air I-95 Exit 77A offers a budget-friendly option that caters primarily to business travellers. The hotel features comfortable accommodations with essential amenities designed to support a productive stay, including complimentary Wi-Fi, a business centre, and meeting facilities. Guests can start their day with a free hot breakfast, ensuring they are energised for their activities. The hotel’s convenient location near the I-95 corridor makes it an ideal choice for those needing easy access to nearby businesses and attractions.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: Situated 33.8km from Chestertown, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A is a budget-friendly hotel known for its pet-friendly policy, receiving a commendable guest rating of 8.2 out of 10. This accommodation is particularly suited for travellers wishing to bring their furry companions along. The hotel offers a range of amenities, including a complimentary breakfast, an outdoor pool, and pet-friendly rooms, ensuring a comfortable stay for both guests and their pets. The welcoming atmosphere and modern facilities make this property a popular choice for families and pet owners alike.
• Americas Best Value Inn Edgewood: Located 33.8km from Chestertown, Americas Best Value Inn Edgewood presents a budget-friendly lodging option with a focus on pet-friendly stays. This hotel allows pets on-site, catering to those travelling with dogs and cats, with specific policies in place regarding deposits and fees. Guests can enjoy essential amenities such as complimentary breakfast, Wi-Fi, and comfortable rooms designed for relaxation after a day of exploring. The Americas Best Value Inn Edgewood prioritises affordability without compromising on convenience, making it a practical choice for pet owners and budget-conscious travellers.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of history and natural beauty, perfect for an outdoor getaway. Stroll through the charming streets of historic Chestertown, where friendly locals and family-friendly attractions abound. Explore the picturesque Eastern Shore, with its serene landscapes and relaxing atmosphere. Whether you're seeking a peaceful retreat or an adventure, Chestertown and its surroundings promise memorable experiences for every traveller.

• Worton: A charming city located a mere 6.4km from Chestertown, Worton is a hidden gem for outdoor enthusiasts. With traveller arrivals peaking in April to May and July, visitors flock here for its stunning natural scenery and recreational areas. Worton features beautiful beaches and serene lakes, making it an ideal spot for those seeking a peaceful retreat. The area offers various outdoor activities, including hiking and picnicking, perfect for families and nature lovers alike.
• Georgetown: Nestled in the vicinity of Chestertown, Georgetown is a delightful village that comes alive during the summer months, particularly from June to August. Known for its romantic atmosphere and vibrant entertainment scene, this quaint village is perfect for couples and those seeking a bit of adventure. Visitors can enjoy local recreation centres, educational opportunities, and scenic hiking trails, all while taking in the beauty of nearby beaches and the stunning marina. Georgetown truly offers a mix of relaxation and activity.
• Tolchester Beach: Located close to Chestertown, Tolchester Beach is a picturesque village that is a favourite among those craving a beach getaway. Although its visitor numbers vary throughout the year, it peaks in May and during the summer months of July and August. The area is renowned for its beautiful family-friendly beaches and marinas, as well as exciting activities like skiing and educational programmes. Tolchester Beach is the perfect destination for families and groups looking to enjoy the great outdoors in a scenic coastal setting.

Things to do in Chestertown

Shopping

In Chestertown, you can explore local shops like The Kitchen at the Old Mill for unique gifts and artisanal products. If you're up for a drive, check out the nearby Annapolis Mall, featuring a variety of retail stores and dining options to enhance your shopping experience.

Recreation

Chestertown Wellness Centre offers a tranquil atmosphere for yoga and meditation, allowing you to reconnect with yourself. Nearby, the Chester River provides opportunities for kayaking and nature walks, immersing you in the peaceful beauty of the Maryland landscape while promoting relaxation and well-being.

Adventure

Explore the scenic Chester River by kayaking, where you can paddle through tranquil waters and enjoy the surrounding wildlife. For those seeking thrills, head to nearby hiking trails that offer breathtaking views and a chance to connect with nature on a deeper level.

Nightlife

Explore the lively atmosphere at The Imperial Hotel on High Street, where you can enjoy a range of local wines. For a more casual vibe, visit The Fish Whistle for fresh seafood and live music, creating a relaxed yet vibrant evening out in Chestertown.

Find the best attractions in and around Chestertown

Chestertown, Maryland, is perfect for those seeking outdoor adventures and scenic beauty. Popular attractions include parks, urban parks, and beaches, making it ideal for families and beach enthusiasts. A must-visit is the historic Chestertown, where you can immerse yourself in local heritage. Enjoy a delightful blend of nature and culture during your stay in this charming town.

• Ferry Park: Located 19.3km from Chestertown, Ferry Park offers a delightful urban oasis. With its family-friendly atmosphere and ample outdoor space, visitors can enjoy leisurely strolls, picnics, or simply relax while soaking in the vibrant city vibes.
• Historical Society of Kent County Maryland: Nestled in Chestertown, this history museum provides a fascinating glimpse into the local heritage. With engaging exhibits and cultural artefacts, it’s an enriching experience for those keen to learn about the region's past.
• River Arts Chestertown: Situated in the heart of Chestertown, this arts centre showcases the creativity of local artists. Visitors can explore various exhibitions, workshops, and events, immersing themselves in the rich cultural tapestry of the community.

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

Flying into Chestertown, Maryland, is convenient via several major airports. Philadelphia International Airport (PHL) is approximately 101.4km away, with excellent hotels like the 5-star W Philadelphia and The Ritz-Carlton, both within 11.3km. Ronald Reagan Washington National Airport (DCA) is located about 93.3km from Chestertown, offering luxurious options such as the InterContinental Washington D.C. - The Wharf and Pendry Washington DC - The Wharf, both just 3.2km from the airport. Additionally, Washington Dulles International Airport (IAD) is around 122.3km away, with nearby hotels like the Hyatt Regency Dulles Airport and The Westin, both only 1.6km from the terminal.