Find and Book Top Rated Hotels in Chestertown

Search among 20 available hotels and places to stay in Chestertown from 50+ providers

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8.2
Great46 reviews
MapView on map2.1 km from City Centre300 m from Kent Plaza Shopping Center
From   US$ 92 /nightSelect
Places to stay near Chestertown
8.2
Great55 reviews
MapView on map33.2 km from Chestertown33.2 km from City Centre
From   US$ 175 /nightSelect
8.6
Great61 reviews
36.1 km from Chestertown36.1 km from City Centre
From   US$ 129 /nightSelect
8.4
Great96 reviews
30.7 km from Chestertown30.7 km from City Centre
From   US$ 184 /nightSelect
8.4
Great71 reviews
36.4 km from Chestertown36.4 km from City Centre
From   US$ 84 /nightSelect
8.4
Great26 reviews
40.9 km from Chestertown40.9 km from City Centre
From   US$ 104 /nightSelect
8.4
Great55 reviews
34.3 km from Chestertown34.3 km from City Centre
From   US$ 121 /nightSelect
8.4
Great29 reviews
37.4 km from Chestertown37.4 km from City Centre
From   US$ 119 /nightSelect
8.4
Great65 reviews
30.8 km from Chestertown30.8 km from City Centre
From   US$ 155 /nightSelect
34.3 km from Chestertown34.3 km from City Centre
From   US$ 147 /nightSelect
8.4
Great54 reviews
34.4 km from Chestertown34.4 km from City Centre
From   US$ 100 /nightSelect
33.8 km from Chestertown33.8 km from City Centre
From   US$ 148 /nightSelect
30.5 km from Chestertown30.5 km from City Centre
From   US$ 346 /nightSelect
8.4
Great44 reviews
37.5 km from Chestertown37.5 km from City Centre
From   US$ 160 /nightSelect
8.2
Great24 reviews
37.4 km from Chestertown37.4 km from City Centre
From   US$ 169 /nightSelect
8.4
Great38 reviews
34.1 km from Chestertown34.1 km from City Centre
From   US$ 239 /nightSelect
8.4
Great40 reviews
17.6 km from Chestertown17.6 km from City Centre
From   US$ 325 /nightSelect
8.6
Great61 reviews
34.7 km from Chestertown34.7 km from City Centre
From   US$ 527 /nightSelect
36.5 km from Chestertown36.5 km from City Centre
From   US$ 126 /nightSelect
8.4
Great38 reviews
17.5 km from Chestertown17.5 km from City Centre
From   US$ 273 /nightSelect

Best hotels and places to stay in Chestertown

Why visit?

Chestertown, Maryland, offers a unique blend of history, natural beauty, and cultural attractions, making it an interesting destination for tourists. With a variety of hotels and places to stay, including Chestertown hotel, hotel Chestertown MD, and motel Chestertown MD, visitors can enjoy comfortable accommodations while exploring the citys charm. From the historical sites and charming downtown area to the waterfront and outdoor activities, Chestertown offers something for everyone.

Where to stay?

Downtown Chestertown: Staying in downtown Chestertown provides easy access to the citys historical sites, shops, and restaurants. With hotels in Chestertown and Chestertown MD hotels, visitors can enjoy a convenient location and immerse themselves in the citys vibrant atmosphere. The proximity to attractions like the Chestertown Historic District, the Washington College campus, and the Garfield Center for the Arts makes it an ideal choice for tourists.

Waterfront Accommodations: For those seeking a tranquil and scenic experience, choosing lodging in Chestertown MD near the waterfront is a great option. Hotels in Chestertown MD offer picturesque views of the Chester River, allowing guests to relax and enjoy the serene surroundings. Visitors can take leisurely walks along the waterfront, go boating or kayaking, or simply admire the beautiful sunsets.

Rural Retreats: Chestertown also offers options for those looking to escape the hustle and bustle of city life. Lodging in Chestertown MD, particularly in the neighboring countryside, provides a peaceful and serene experience. Many bed and breakfasts and country inns offer a cozy and comfortable stay with the charm of rural living. Guests can enjoy exploring nearby farms, vineyards, or simply taking in the scenic beauty of the Chesapeake Bay area.

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 $500.

Best value for money:

Chestertown Inn: Located in downtown Chestertown, this charming hotel offers comfortable rooms with modern amenities and a friendly staff. With its affordable rates and convenient location, it provides excellent value for money for travelers. (Keywords: hotel Chestertown MD, hotels in Chestertown, lodging Chestertown MD)

Holiday Inn Express Chestertown: This well-known chain hotel offers comfortable rooms and a range of amenities, including a complimentary breakfast buffet and an indoor pool. It provides great value for families or business travelers looking for a convenient stay. (Keywords: Chestertown MD hotel, hotels Chestertown MD, places to stay in Chestertown MD)

Simply Bed & Breakfast: If you prefer a more intimate and budget-friendly option, this bed and breakfast offers cozy rooms and personalized service. With its central location and affordable rates, it is an excellent choice for those seeking a unique and affordable experience. (Keywords: Chestertown MD lodging, hotel in Chestertown MD, motels in Chestertown MD)

Best kids-friendly hotels:

Driftwood Inn: Situated near the waterfront, this family-friendly hotel offers spacious rooms and a range of amenities suitable for children, including a playground and a picnic area. It is an ideal choice for families looking for a fun and comfortable stay. (Keywords: hotels Chestertown Maryland, hotels in Chestertown MD)

Brampton Bed and Breakfast Inn: This charming inn provides family-friendly accommodations with spacious rooms and beautiful gardens to explore. Additionally, they offer complimentary activities for children, such as board games and outdoor sports equipment, ensuring an enjoyable stay for the whole family. (Keywords: motels in Chestertown Maryland, places to stay in Chestertown MD)

Best hotels for a romantic getaway:

Great Oak Manor: Overlooking the Chesapeake Bay, this elegant bed and breakfast offers luxurious rooms with breathtaking views. With its peaceful surroundings and attentive service, it creates a perfect ambiance for a romantic escape. (Keywords: Chestertown MD hotels, hotels Chestertown MD)

The Inn at Mitchell House: Set in a historic property, this inn offers romantic rooms with period decor and modern amenities. Guests can enjoy serene gardens and a delicious homemade breakfast, making it an ideal choice for couples seeking a romantic retreat. (Keywords: hotel Chestertown MD, hotels in Chestertown MD)

Best for location:

Front Street Inn: Located in the heart of downtown Chestertown, this inn provides easy access to the citys attractions, shops, and restaurants. With its prime location, guests can explore the area on foot and experience the vibrant atmosphere. (Keywords: motel Chestertown MD, places to stay in Chestertown MD)

Brampton Bed and Breakfast Inn: Situated on a 35-acre estate, this inn offers a peaceful and secluded setting while still being close to downtown Chestertown. Guests can enjoy the best of both worlds: a serene escape and easy access to the towns amenities. (Keywords: Chestertown hotel, lodging Chestertown MD)

Crow Farmstay B&B: Located just outside Chestertown, this picturesque bed and breakfast offers a tranquil countryside retreat. Guests can enjoy the peaceful surroundings and scenic views while still being within a short drive from the city center. (Keywords: hotels in Chestertown, Chestertown MD lodging)

Best for a short city break:

Quality Suites Chestertown: This all-suite hotel offers spacious accommodations with separate living areas, making it a comfortable option for a short visit. Its location near downtown Chestertown allows guests to easily explore the citys attractions and dining options. (Keywords: hotel Chestertown MD, Chestertown MD hotel)

Rolphs Wharf Marina & Waterfront Farm: This unique property offers waterfront cabins with beautiful views and direct water access. Guests can unwind and enjoy a relaxing break surrounded by nature while still being in close proximity to Chestertowns amenities. (Keywords: motels in Chestertown MD, hotels in Chestertown MD)

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