Find Romantic Hotels in Chestertown, NY from $121

Chestertown attractions for couples

Chestertown, New York, offers a delightful array of experiences for the discerning traveler. Start your exploration at the stunning Loon Lake, where families can enjoy kayaking and paddleboarding amidst serene natural beauty. The nearby Chester Historical Society showcases the town's rich heritage with engaging exhibits that will captivate both adults and children alike. For outdoor enthusiasts, the Gore Mountain ski resort is just a short drive away, providing exceptional skiing opportunities in winter and mountain biking trails in summer. Nature lovers will appreciate the breathtaking hiking trails at the nearby Adirondack Park, with routes suitable for all skill levels. After a day of adventure, consider staying at one of the charming inns or lodges in the area, where attentive service and cozy accommodations create a welcoming atmosphere. The local dining scene, featuring farm-to-table options, adds to the experience, making every meal a delightful end to your day in Chestertown.

Find the best romantic hotels in Chestertown

For couples seeking a romantic getaway in Chestertown, New York, these hotels offer intimate settings and amenities perfect for enhancing your experience together.

The Fern Lodge

• Why it's great for a couples retreat: With an outstanding review rating of 10.0, The Fern Lodge is an idyllic retreat for couples looking to unwind and reconnect. This romantic sanctuary features a private hot tub and elegant jetted bathtubs, perfect for relaxing evenings after a day of adventure. Guests can enjoy romantic riverside views and cozy up by the fireplace in their rooms, enhancing the intimate atmosphere.
• Other amenities: Guests will also benefit from free breakfast for a perfect start to your day, and the opportunity for massages, including in-room options, to further pamper yourselves. The hotel provides a terrace, air conditioning, and beautiful gardens, alongside diverse outdoor activities such as kayaking and hiking, making it a well-rounded romantic getaway.
• Nearby attractions: Friends Lake - 0.26 miles, Loon Lake - 3.97 miles

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

• Why it's great for a couples retreat: For couples looking for adventure combined with romance, the Modern Cabin w/ Hot Tub is a fantastic choice with a perfect review rating of 10.0. The cabin’s hot tub offers an excellent opportunity for relaxation after a day of exploring, while the nearby lakes and skiing options provide exhilarating activities for couples to enjoy together.
• Other amenities: The hotel features a cozy indoor atmosphere with a fully equipped kitchen, perfect for preparing intimate meals. Guests will also appreciate the patio for outdoor dining, air conditioning for comfort, and nearby local shopping and dining options. With additional amenities like a garden and nearby hiking opportunities, this cabin is a perfect romantic getaway.
• Nearby attractions: Loon Lake - 1.47 miles, Loon Lake Beach - 1.5 miles

Pine Tree Motel & Cabins

• Why it's great for a couples retreat: Pine Tree Motel & Cabins offers couples an affordable yet charming escape with a solid review rating of 9.0. Nestled in nature, this hotel features cozy yards and patios ideal for intimate evenings under the stars. Although the motel itself has limited romantic amenities, its tranquil setting and beautiful surroundings provide the perfect backdrop for a romantic retreat.
• Other amenities: Couples can explore nearby beaches and hiking trails, enjoying outdoor activities together. The motel also offers conveniences such as air conditioning, self-parking, and daily housekeeping to ensure a comfortable stay. With unique local attractions like motorboating and kayaking nearby, couples can create lasting memories during their visit.
• Nearby attractions: Loon Lake - 0.58 miles, Loon Lake Beach - 0.61 miles

Friends Lake Inn

• Why it's great for a couples retreat: For a romantic escape, Friends Lake Inn is an enchanting choice with its captivating atmosphere and a strong guest review rating of 8.4. Couples can indulge in personalized dining experiences that create an intimate setting, complemented by the cozy ambiance highlighted by fireplaces and luxurious bathrobes for those special moments together.
• Other amenities: Additional amenities include a terrace for leisurely strolls, complimentary champagne service to toast your love, and opportunities for outdoor adventures like hiking, snowshoeing, and kayaking nearby. Guests will also appreciate the onsite billiards, air conditioning for comfort, and free toiletries, ensuring a delightful and memorable stay in the breathtaking surroundings of the mountains.
• Nearby attractions: Friends Lake - 0.21 miles, Loon Lake Beach - 2.52 miles