Look for hotels in Chestertown, Maryland

Looking for a charming getaway? Look no further than Chestertown, a historic town in Maryland that is sure to steal your heart. This quaint little town is known for its stunning waterfront and beautiful brick mansions. Whether you're a history buff or just looking for a peaceful escape, Chestertown is the perfect destination for you.

When it comes to accommodations, Chestertown has a variety of charming hotels that will make your stay memorable. Imagine waking up in a cozy bed, surrounded by the historic charm of the town. From boutique hotels to charming bed and breakfasts, you'll find the perfect place to rest your head after a day of exploring.

While you're in town, be sure to check out the Chestertown Tea Party Festival, a celebration of the town's colonial heritage. Watch as re-enactors recreate the famous "tea party" on the Chester River, or join in on the colonial music and dance performances. And don't forget to take a stroll down the town's main street on First Friday, when local shops open their doors and put their merchandise on display.

So why wait? Pack your bags and head to Chestertown, where history meets charm and relaxation awaits. Whether you're exploring the historic district or enjoying the scenic beauty of the waterfront, Chestertown is a hidden gem that is sure to leave a lasting impression. Don't miss out on the opportunity to experience the magic of this charming town. Book your stay today and discover the beauty of Chestertown for yourself.

Best Hotels in Chestertown

Brampton Bed and Breakfast Inn

Pet Friendly

Free Private Parking

Adults only

The Brampton Bed and Breakfast Inn, located in Chestertown, Maryland, is a 5-star hotel that sets itself apart from others with its exceptional amenities and services. Guests can enjoy a delicious breakfast each morning, making their stay even more convenient. The inn is also pet-friendly, allowing guests to bring their furry friends along. With private parking, free WiFi, a spa tub, and air conditioning, guests can expect a comfortable and luxurious stay. The beautiful garden view, picnic area, and terrace provide a serene and relaxing atmosphere. Additionally, the Inn offers non-smoking rooms and extra-long beds for added comfort.

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From

$283

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Comfort Inn & Suites Chestertown

Free parking

Free wifi

Air conditioning

Welcome to Comfort Inn & Suites Chestertown, a 2-star hotel conveniently located just 1.3mi from the city center of Chestertown, Maryland. What sets us apart from others is our commitment to guest satisfaction. Start your day off right with our complimentary breakfast, and enjoy our free WiFi throughout the hotel. Stay active in our fitness center or on our golf course for an additional charge. Our 24-hour front desk and business center are available to meet your needs. With amenities like free parking, air conditioning, and non-smoking rooms, we strive to make your stay comfortable and convenient.

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From

$110

Check availability

Which 5-star hotels are the most popular?

The Brampton Bed and Breakfast Inn is a popular 5-star hotel in Chestertown city. With prices starting from $283, the inn offers a delightful stay in a peaceful setting. Located just 1.5mi from the city center, guests can enjoy easy access to all the attractions the city has to offer.

One of the standout features of the Brampton Bed and Breakfast Inn is their delicious breakfast, which is included in the stay. Guests can start their day off right with a hearty meal before heading out to explore Chestertown. The inn also caters to pet owners, offering a pet-friendly environment. In addition, the inn provides free private parking for guests, making it convenient for those traveling by car.

The amenities at Brampton Bed and Breakfast Inn are designed to provide comfort and relaxation. The inn features a spa tub, perfect for unwinding after a long day of sightseeing. The rooms are equipped with air conditioning and offer garden views, creating a tranquil atmosphere. The beds are extra long, measuring over 6.5ft, ensuring a comfortable sleep. The inn also offers free WiFi, allowing guests to stay connected during their stay.