Best Hotels and Places to Stay in Chestertown
Why visit?
Chestertown, MD is a charming town located on Marylands eastern shore, making it an ideal destination for tourists seeking a relaxing getaway. With its rich history, scenic waterfront, and quaint downtown area, Chestertown offers a unique blend of attractions and activities. Visitors can enjoy exploring the historic district, taking a leisurely stroll along the Chester River, and immersing themselves in the towns vibrant arts and cultural scene. Whether youre looking for outdoor adventures, historical landmarks, or simply a peaceful retreat, Chestertown has something to offer every kind of traveler.
Where to stay?
Historic District: Staying in the heart of Chestertowns Historic District allows you to immerse yourself in the towns rich heritage. This area is home to numerous boutique hotels, bed and breakfasts, and charming inns that provide a cozy and historical ambiance. With close proximity to the towns main attractions, including the Chestertown Farmers Market and the Kent County Courthouse, youll have plenty to explore within walking distance.
Waterfront: For those looking for a picturesque stay, the waterfront area of Chestertown is an excellent choice. Overlooking the tranquil Chester River, this neighborhood offers stunning views and a serene atmosphere. There are a variety of waterfront hotels and resorts that provide direct access to the river, allowing you to enjoy activities such as boating, fishing, and waterfront dining. Additionally, the waterfront area is known for its beautiful parks and nature trails, offering opportunities to embrace the outdoors.
Campus Area: Chestertown is also home to Washington College, a prestigious liberal arts institution founded in 1782. Staying near the campus area provides a vibrant and youthful atmosphere. You can find accommodations such as modern hotels and guesthouses with easy access to the colleges facilities and events. In addition, the campus area offers proximity to dining options, shops, and art galleries, making it a convenient choice for visitors looking for a lively and collegiate experience.
What is the price per hotel room per night?
3-star hotels: The average price per night is around $100 to $150.
4-star hotels: The average price per night is around $150 to $250.
5-star hotels: The average price per night is around $250 to $400.
Best value for money:
Kent Manor Inn: Located just outside of Chestertown, the Kent Manor Inn offers comfortable accommodations at an affordable price. This charming inn features spacious rooms with modern amenities, including free Wi-Fi and flat-screen TVs. Guests can enjoy the peaceful surroundings, beautiful gardens, and access to outdoor activities such as fishing and kayaking. With its reasonable rates and convenient location, the Kent Manor Inn is a great choice for those seeking a budget-friendly option.
Holiday Inn Express Hotel & Suites Chestertown: Situated in the heart of Chestertown, the Holiday Inn Express Hotel & Suites offers a comfortable stay with excellent value for money. The hotel features clean and spacious rooms with comfortable beds, free breakfast, and a fitness center. Additionally, its central location provides easy access to local attractions, restaurants, and shops. With its affordable pricing and convenient amenities, the Holiday Inn Express Hotel & Suites is an ideal choice for budget-conscious travelers.
Driftwood Inn: The Driftwood Inn is a cozy and affordable option located near Chestertowns waterfront. This family-owned motel offers clean and comfortable rooms with basic amenities, including free Wi-Fi and cable TV. Guests can enjoy the motels scenic views and outdoor seating area. The Driftwood Inn is a popular choice for those looking for a budget-friendly stay with a relaxed atmosphere.
Best kids-friendly hotels:
Widmyer: Located within close proximity to family-friendly attractions, the Widmyer Hotel is a great choice for families visiting Chestertown. This hotel offers spacious rooms and suites with kid-friendly amenities such as mini-fridges and microwaves. The hotel also features an indoor pool, complimentary breakfast, and a game room for children to enjoy. With its convenient location and family-oriented amenities, the Widmyer Hotel caters to the needs of both parents and children.
Great Oak Manor: Nestled on the waterfront, the Great Oak Manor provides an unforgettable experience for families. This elegant bed and breakfast offers spacious rooms and suites, some with private balconies and stunning water views. Families can take advantage of the propertys expansive lawn, outdoor activities, and even a private beach. The Great Oak Manor offers a serene and picturesque setting where both parents and children can create lasting memories.
Best hotels for a romantic getaway:
The Imperial Hotel: Set in a beautifully restored historic building, The Imperial Hotel offers a romantic ambiance for couples seeking a getaway. The hotel features luxurious rooms with antique furnishings and modern amenities. Guests can enjoy a romantic dinner at the hotels on-site restaurant, which offers fine dining options. With its intimate setting and attention to detail, The Imperial Hotel is perfect for couples looking for a romantic retreat.
Brampton Inn: Surrounded by sprawling gardens and countryside views, Brampton Inn offers a tranquil escape for couples. This charming bed and breakfast features elegantly decorated rooms, some with fireplaces and whirlpool tubs. Couples can enjoy a delicious breakfast each morning and relax in the inns peaceful atmosphere. With its romantic setting and personalized service, Brampton Inn is an idyllic choice for a romantic getaway.
Best for location:
The Waterfront House: Situated directly on the waterfront, The Waterfront House offers breathtaking views of the Chester River. This boutique hotel features beautifully appointed rooms with private balconies overlooking the water. Guests can enjoy easy access to water activities, as well as the convenience of being within walking distance to downtown Chestertowns shops and restaurants.
Inn at Mitchell House: Nestled in a picturesque countryside setting, the Inn at Mitchell House provides a peaceful retreat while still being close to Chestertowns main attractions. This historic bed and breakfast offers charming rooms with period details and modern amenities. Guests can enjoy the inns tranquil gardens and take advantage of its close proximity to outdoor activities such as hiking and cycling.
Brampton Bed and Breakfast Inn: Located just a short drive from downtown Chestertown, Brampton Bed and Breakfast Inn offers a serene and secluded setting. Surrounded by acres of farmland, this inn provides a peaceful escape from the hustle and bustle. Guests can relax in beautifully appointed rooms, savor gourmet breakfasts, and unwind on the inns peaceful grounds. Despite its peaceful location, the inn is conveniently located near popular attractions and activities.
Best for a short city break:
The Dixon House: Centrally located in Chestertowns Historic District, The Dixon House offers easy access to the towns shops, restaurants, and historical landmarks. This boutique hotel provides stylish rooms with modern amenities to ensure a comfortable stay. Guests can explore the town by foot or relax on the hotels charming rooftop terrace, offering panoramic views of Chestertown.
Quality Suites Chestertown: Located near Washington College, Quality Suites Chestertown offers a convenient base for a short city break. This modern hotel features spacious suites equipped with living areas and kitchenettes. Guests can enjoy the hotels fitness center, complimentary breakfast, and close proximity to downtown Chestertowns attractions. With its comfortable accommodations and central location, Quality Suites Chestertown is perfect for a short getaway.
