Search 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

Pet Friendly

Friends Lake Inn is a 5-star Inn located in Chestertown, New York. This charming inn offers a wide range of amenities including skiing, free parking, pet-friendly accommodations, complimentary Wi-Fi, a spa tub, and a golf course (extra charges apply). With a 24-hour front desk and non-smoking rooms, this inn provides exceptional service and comfort to guests. The inn also boasts a bar and restaurant, perfect for enjoying a delicious meal or relaxing with a drink. With beautiful views, a welcoming atmosphere, and an array of amenities, Friends Lake Inn stands out as the perfect choice for a memorable stay.

Show more

From

$247

Check availability

Which 5-star hotels are the most popular?

Friends Lake Inn is a popular 5-star hotel located just 2.6mi away from Chestertown city center. With prices starting from $247 per night, this luxurious property offers a range of amenities to provide guests with an unforgettable stay. Some of the featured amenities include skiing, free parking, and pet-friendly accommodations. Guests can also enjoy free WiFi, a spa tub, and access to a golf course for an additional charge. The hotel provides a 24-hour front desk, non-smoking rooms, and a bar and restaurant for guests to relax and indulge in delicious meals and refreshing drinks. The scenic views, sun deck, and terrace add to the overall charm of this elegant hotel.

At Friends Lake Inn, guests can expect exceptional services and additional amenities to enhance their experience. The hotel offers grocery deliveries for an additional charge, a shared lounge/TV area, and a designated smoking area. For those looking to explore the outdoors, the hotel provides horseback riding and hiking options, as well as a pool table and game room for indoor entertainment. Wine and champagne are available for purchase, along with special diet meals upon request. The hotel also offers massage services, concierge assistance, and baggage storage. Daily housekeeping, fax/photocopying services, and meeting/banquet facilities are available for guests on business trips.

Staying at Friends Lake Inn guarantees a comfortable and luxurious experience. The hotel offers well-equipped rooms with various amenities, including a private bathroom with a bathtub, free toiletries, and a terrace or view. Guests can relax in air-conditioned rooms with a walk-in closet, flat-screen TV, and comfortable sofa. The hotel provides all essential items such as towels, linens, and a hairdryer. The rooms also feature a cozy fireplace, adding a touch of warmth and elegance to the ambiance. Additional room features include a coffee machine, hardwood or parquet floors, and a socket near the bed for convenience. Overall, Friends Lake Inn is the perfect destination for travelers seeking a luxurious and enjoyable stay in Chestertown.