Find all hotels by Independent in Chestertown, MD from $69

The best area to stay in Chestertown is the historic downtown area, particularly near the Chester River waterfront.

This neighborhood is the heart of Chestertown, characterized by its well-preserved 18th-century architecture and tree-lined streets. It's very walkable, with most shops, restaurants, and historic sites concentrated around High Street and Water Street. The Custom House and the Garfield Center for the Arts are popular landmarks within easy walking distance.

Couples often find this area ideal for a relaxed and scenic getaway. The proximity to the Chester River allows for strolls along the waterfront and easy access to picturesque views. The downtown area also offers a selection of independent boutiques and dining options superb for an evening out.

For those interested in history and local culture, staying in the historic downtown puts you right in the middle of Chestertown's heritage.

Two of the best hotels in Chestertown that travelers recommend are the Comfort Inn & Suites Chestertown and The Lodge at Great Oak Landing.

The Comfort Inn & Suites Chestertown, with an 8.6 rating, is frequently praised for its comfortable and clean rooms, as well as its friendly and helpful staff. Guests particularly appreciate the complimentary full breakfast offered.

Another highly recommended option is the 3.5-star The Lodge at Great Oak Landing, which has an 8.0 rating. This hotel is known for its friendly and helpful staff, excellent food, and comfortable rooms. It offers an onsite golf course, stunning water views, and a marina view, along with a shared, secured pool area with lounge chairs and umbrellas.

For family-friendly hotels in Chestertown, consider the Comfort Inn & Suites Chestertown and The Lodge at Great Oak Landing.

The Comfort Inn & Suites Chestertown is a highly-rated option with an 8.6 review score. Guests consistently describe the rooms as comfortable and clean, and the staff as friendly and helpful. The hotel offers amenities such as a pool, pool gate, child-friendly window design, cribs, and sofa beds, making it well-suited for families. The complimentary breakfast is also a popular feature.

Another excellent choice for families is The Lodge at Great Oak Landing, a 3.5-star hotel with an 8.0 rating. This property features a pool with umbrellas and sun loungers, a playground for children, and connecting rooms, which can be very convenient for families. Many rooms offer water or marina views. Guests frequently praise the friendly and helpful staff, the great restaurant, and the great and comfortable rooms. Find more child-friendly accommodations in Chestertown

For hotels in Chestertown that offer complimentary breakfast, the Comfort Inn & Suites Chestertown is an excellent option.

The Comfort Inn & Suites Chestertown, with an 8.6 rating, provides a full free breakfast, which guests consistently praise as a nice amenity. This hotel also offers free internet and free WiFi, along with complimentary self-parking. Guests frequently mention the comfortable and clean rooms and beds, as well as the friendly and helpful staff, particularly at the front desk. For those traveling with pets, the Chestertown Dog Park is conveniently located just 0.7 miles away. Find more hotels with free breakfast in Chestertown

For top pet-friendly hotels in Chestertown, consider the Comfort Inn & Suites Chestertown, the Red Roof Inn & Suites Chestertown, and the Driftwood Inn.

The 3-star Comfort Inn & Suites Chestertown, with an 8.6 rating, is a highly-rated option. It offers a complimentary full breakfast and early check-in, making your arrival smooth. Guests frequently highlight the comfortable and clean rooms and the friendly and helpful staff. It is conveniently located near the Chestertown Dog Park and Rolling Road Park, both within 0.7 miles.

Another good choice is the Red Roof Inn & Suites Chestertown, rated 7.2. This hotel permits both dogs and cats, making it a flexible option for pet owners. Travelers often mention the comfortable and clean rooms, the nice coffee, and the friendly front desk staff. Easy parking is also a plus. It is also close to the Chestertown Dog Park and Rolling Road Park, both 0.6 miles away.

The Driftwood Inn is another pet-friendly accommodation that offers free self-parking and complimentary WiFi. Guests appreciate the clean rooms and friendly staff. It is located near the Garfield Center for the Arts at the Prince Theater, River Arts Chestertown, and Wilmer Park, all within 1.2 miles. See more pet-friendly hotels in Chestertown

For budget-friendly accommodations in Chestertown, consider the Comfort Inn & Suites Chestertown, the Red Roof Inn & Suites Chestertown, or the Driftwood Inn.

The Comfort Inn & Suites Chestertown, rated 8.6, offers a comfortable stay with complimentary internet, free toiletries, and a free full breakfast. Guests frequently mention the comfortable and clean rooms and beds, as well as the friendly and helpful staff. It is conveniently located near Chestertown Dog Park and Rolling Road Park, both within 0.7 miles.

Another option is the Red Roof Inn & Suites Chestertown, with a rating of 7.2. This hotel provides free WiFi, complimentary self-parking, and free wired internet. Guests often highlight the comfortable and clean rooms, the nice staff, and easy parking. It is also close to Chestertown Dog Park and Rolling Road Park, both 0.6 miles away.

The Driftwood Inn offers free WiFi, complimentary self-parking, and free toiletries. Guests appreciate the clean rooms and friendly staff. This inn is located 0.5 miles from Chestertown Dog Park and Rolling Road Park, and just a bit further to the Chestertown Historic District and Sumner Hall. View all budget hotels in Chestertown

The Lodge at Great Oak Landing is an excellent choice for couples seeking a romantic stay in Chestertown.

This 3.5-star hotel, rated 8.0, offers beautiful water and marina views, providing a serene backdrop for a couples' getaway. Guests frequently praise the friendly and helpful staff, the great restaurant with delicious food, and the perfect, comfortable rooms. The shared pool with sun loungers and umbrellas offers a relaxing spot to unwind together. Many rooms also feature a furnished balcony, superb for enjoying the scenic surroundings. See all romantic hotels in Chestertown

For a well-located hotel in Chestertown near Wilmer Park, consider the Driftwood Inn.

The Driftwood Inn offers amenities such as free WiFi, complimentary self-parking, and free toiletries. Guests have consistently praised the clean rooms and friendly staff. It is conveniently located 1.2 miles from Wilmer Park, making it a good choice for those wanting to be close to the park.

The best time to visit Chestertown for enjoyable weather and activities is during the spring (April to June) and fall (September to October).

Springtime in Chestertown brings mild temperatures, typically ranging from the low 60s to high 70s Fahrenheit. The town's gardens and parks are in full bloom, making it an ideal time for leisurely strolls along the Chester River waterfront or exploring the historic district's tree-lined streets. Events like the Chestertown Tea Party Festival in May offer a lively experience with reenactments and local crafts.

Fall offers pleasant temperatures, usually from the 50s to 70s Fahrenheit, with less humidity than summer. The changing leaves create picturesque scenery, particularly along the river and in the surrounding countryside. This season is superb for outdoor activities like kayaking on the Chester River or visiting local farms.

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chestertown.

Prices for hotels in Chestertown often vary, but you can find a great deal from $69 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.