Hotels in Chestertown, New York

Looking for a charming and historic getaway? Look no further than Chestertown, Maryland! With its picturesque waterfront, brick mansions, and colonial heritage, this town is a hidden gem waiting to be explored. As one of Maryland's six Royal Ports of Entry, Chestertown's shipping boom in the 18th century brought wealth and prosperity to the town. Today, visitors can stroll along the historic district, marvel at the beautifully preserved 18th-century homes, and even participate in the famous Chestertown Tea Party Festival, where locals reenact the colonial defiance to the British tea tax by throwing tea into the Chester River. And for those looking to indulge in some nautical adventure, don't miss the opportunity to board the schooner Sultana, an American-built yacht, for an educational trip. With its rich history and vibrant culture, Chestertown is the perfect destination for travelers who appreciate both charm and character.

When it comes to accommodations, Chestertown offers a variety of options to suit every traveler's needs. From cozy bed and breakfasts with warm hospitality to boutique hotels with modern amenities, there's something for everyone. Imagine waking up to the smell of freshly brewed coffee and enjoying a delicious homemade breakfast before embarking on a day of exploring the town. After a day of sightseeing, unwind in a luxurious hotel room, complete with plush bedding and stunning views of the waterfront. Whether you prefer a quaint inn with traditional charm or a contemporary hotel with all the comforts of home, you'll find the perfect place to rest your head in Chestertown.

Don't miss out on the opportunity to experience Chestertown's unique blend of history, culture, and hospitality. From its rich colonial heritage to its vibrant arts and cultural scene, this town has something to offer every traveler. So pack your bags, book your stay, and get ready for an unforgettable adventure in the charming town of Chestertown.

Best Hotels in Chestertown

Friends Lake Inn

Skiing

Free parking

Restaurant

Experience the unparalleled charm of Friends Lake Inn, a five-star haven nestled just 2.6mi from Chestertown's city center. This premier inn stands out with its exceptional amenities, including free Wi-Fi, a relaxing spa tub, and a sauna to unwind after a day of skiing or golfing. Guests can enjoy delicious meals at the on-site restaurant or unwind on the sun deck with stunning views. With free on-site parking, a tour desk, and various activities such as horseback riding and massage services, Friends Lake Inn truly offers a perfect blend of luxury, comfort, and adventure for all travelers.

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From

$275

Check availability

Conways Lake Manor

Beachfront

Private beach area

Free Private Parking

Conways Lake Manor in Chestertown, United States, offers a unique experience with its beachfront location, private beach area, and free amenities such as Wi-Fi and air conditioning. Guests can enjoy stunning views of the mountain, lake, river, and nearby landmarks from the comfort of non-smoking rooms with private bathrooms and free toiletries. The motel also provides a range of outdoor facilities including a golf course (extra charges may apply), picnic area, sun deck, barbecue, and garden, making it an ideal choice for travelers seeking a relaxing lakeside retreat with convenient on-site parking.

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From

$300

Check availability

Which 5-star hotels are the most popular?

Nestled just 2.6mi from the bustling city center of Chestertown, Friends Lake Inn beckons with its charming allure. Priced starting at $275, this luxurious 5-star hotel offers an array of exquisite amenities to ensure a delightful stay. From the thrill of skiing to the indulgence of a spa tub and sauna, guests can unwind in style. The presence of a golf course, though with additional charges, promises a leisurely round for enthusiasts.

Within the premises of Friends Lake Inn, guests are treated to complimentary Wi-Fi, parking, and air conditioning, ensuring a seamless and comfortable experience. The culinary delights extend beyond the boundaries of the restaurant, with kids' meals available for an extra charge. The 24-hour front desk caters to every need, while the bar and sun deck provide spaces to relax and socialize. The hotel's picturesque garden and terrace offer stunning views, creating an ambiance of tranquility and charm. Guests can retire to their non-smoking rooms equipped with free toiletries, a bathtub, and a private bathroom, culminating in a rejuvenating retreat.