Best Hotels Near Chestertown, Maryland

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Katerina Kore

Updated: 02 February 2024 · 3 min

Nestled on the banks of the Chester River, Chestertown is a hidden gem in Maryland, offering travelers a unique blend of colonial history, vibrant arts scene, and serene natural landscapes. As you plan your visit to this charming town, finding the perfect accommodation becomes a key part of the experience. Hotels near Chestertown provide guests with a comfortable base to explore the myriad attractions the area has to offer, blending convenience with the warm hospitality Maryland is known for.

Choosing the right hotel near Chestertown means more than just a place to rest your head; it's about enhancing your travel experience. Recommendations range from quaint bed and breakfasts offering a personalized touch, to waterfront hotels that allow guests to wake up to breathtaking views of the Chester River. These accommodations often serve as gateways to exploring Chestertown's rich history, its vibrant arts festivals, and the natural beauty that surrounds the town.

Insights into the best hotels near Chestertown reveal more than just amenities and location; they highlight the experiences that await in this quaint town. From enjoying local cuisine at a hotel's in-house restaurant to the convenience of being just a short walk from Chestertown's historic districts, choosing the right hotel can transform a simple visit into a memorable journey. As you delve into this article, you'll uncover the top hotels that promise to make your stay in Chestertown as enriching as it is comfortable.
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Our Top 5

(Sorted by rating & number of reviews)

1. Driftwood Inn
2. Brampton Bed And Breakfast Inn
3. Quality Suites
4. Comfort Inn & Suites Chestertown
5. Wren Retweet Villa

Budget-Friendly Hotels Near Chestertown MD

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Chestertown
Mar 23, 2026 - Mar 24, 2026

Driftwood Inn

5.8

Good

(90 Reviews)

+ 43 photos
The Driftwood Inn provides a comfortable and scenic retreat for those looking to enjoy the waterfront charms of Chestertown. Situated close to the Chester River, guests have access to stunning water views and can easily engage in activities such as kayaking, fishing, or taking leisurely walks along the shore. The inn offers a variety of rooms to fit various guest needs, each designed to provide a relaxing stay with amenities like free Wi-Fi and cable TV. The Driftwood Inn's dedication to hospitality, combined with its prime location near the river, makes it a favored choice for visitors seeking hotels near Chestertown with a waterfront experience.
Address: 609 Washington Avenue
Rating: Good 5.8 (90 Reviews)
Rooms: 18
Price: From 57$

Brampton Bed And Breakfast Inn

9.5

Good

(33 Reviews)

+ 100 photos
Brampton Bed and Breakfast Inn is where historical elegance meets modern comfort. This antebellum estate, nestled on acres of beautifully landscaped gardens, provides a tranquil retreat just a short drive from downtown Chestertown. Guests can choose from elegantly appointed rooms and suites, each with its own unique charm and amenities such as fireplaces and private baths. A gourmet breakfast is served each morning, featuring locally sourced ingredients and homemade specialties. The inn's attentive staff, serene setting, and commitment to providing an exceptional experience make it a premier choice for luxury accommodations near Chestertown you're exploring the nearby nature trails or relaxing in the cozy guest parlor, the Brampton Bed and Breakfast Inn ensures a stay that's as memorable as it is comfortable.
Address: 25227 Chestertown Road
Rating: Good 9.5 (33 Reviews)
Rooms: 13
Price: From 377$

Luxury and Historic Hotels Near Chestertown MD

For those wanting to indulge in a bit of luxury or immerse themselves in the historical charm of Chestertown, there are accommodations that offer an elevated experience. This section presents hotels known for their exquisite architecture, personalized service, and unique connection to the town's heritage. These establishments provide more than just a place to stay; they offer an immersive journey into the elegance and history of Chestertown, catering to guests seeking a memorable and luxurious escape near Chestertown .

Quality Suites

8.3

Good

(57 Reviews)

+ 70 photos
Quality Suites provides a comfortable and convenient stay for travelers looking to explore Chestertown without breaking the bank. Guests can enjoy spacious suites equipped with essential amenities such as free WiFi, coffee makers, and cozy seating areas. A complimentary breakfast is served daily, ensuring a pleasant start to your day. The hotel's location near popular Chestertown attractions, including the Historical Society of Kent County, makes it an excellent base for sightseeing. With its friendly service, comfortable accommodations, and commitment to quality, Quality Suites is a standout option for those seeking value-driven hotels near Chestertown .
Address: 160 Scheeler Rd.
Rating: Good 8.3 (57 Reviews)
Rooms: 53
Price: From 75$

Comfort Inn & Suites Chestertown

7.5

Good

(252 Reviews)

+ 98 photos
Comfort Inn & Suites Chestertown is an excellent option for travelers seeking affordability without sacrificing comfort. Located a convenient distance from the heart of Chestertown, this hotel offers guests a range of amenities including complimentary breakfast, free WiFi, and an indoor pool. Rooms are equipped with modern conveniences such as microwaves and refrigerators, making it an ideal choice for both short visits and extended stays. Proximity to Chestertown's historic district and the Chester River ensures guests can easily explore the local area. The hotel's friendly staff and clean, comfortable rooms make it a top pick for travelers looking for great value hotels near Chestertown .
Address: 150 Scheeler Road
Rating: Good 7.5 (252 Reviews)
Rooms: 81
Price: From 92$

Waterfront Hotels Near Chestertown MD

Chestertown, with its beautiful location by the Chester River, offers visitors the chance to stay close to the water and enjoy the serene views and activities associated with waterfront living. The hotels in this section cater to those who love being near the water, whether it's for the scenic views, boating, or simply the peaceful ambiance that a riverfront provides. These hotels near Chestertown are selected for their proximity to the water, offering guests unique experiences that take full advantage of the area's natural beauty.

Wren Retweet Villa

+ 42 photos
Wren Retweet combines the comfort and convenience travelers look for in accommodations with the added bonus of being pet-friendly. Recognizing the bond between pets and their owners, this establishment offers a welcoming atmosphere for pets, including designated outdoor areas for leisure and play. Rooms are spacious and well-appointed, ensuring both you and your pet have a comfortable stay. The hotel's location allows easy access to several local parks and trails, perfect for morning walks or adventures with your furry companion. Wren Retweet's commitment to providing a pet-friendly environment, along with its excellent facilities, positions it as a top choice for travelers searching for pet-friendly hotels near Chestertown .
Address: 214 North Mill Street

Pet-Friendly Hotels Near Chestertown MD

Traveling with pets can be challenging, but in Chestertown, several hotels welcome your furry friends with open arms. These pet-friendly hotels ensure that no member of the family is left behind on your travels. Offering amenities like pet beds, treats, and special areas for walks, these accommodations understand the needs of pet owners and work hard to provide a comfortable stay for both humans and pets. Here, we highlight the best pet-friendly hotels near Chestertown that make traveling with pets a breeze.