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Find Romantic Hotels in Chestertown, NY from $248

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Check availability on Chestertown Romantic Hotels

Check prices for these dates

Tonight
Jul 8 - Jul 9
Tomorrow
Jul 9 - Jul 10
This weekend
Jul 11 - Jul 13
Next weekend
Jul 18 - Jul 20

Top Chestertown Romantic Hotels

Friends Lake Inn
Premier Room | 1 bedroom, premium bedding, individually decorated

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (90)
"Quiet lodging and friendly staff"
$223 nightly
The price is $248
Jul 9 - Jul 10
Total includes taxes and fees
Friends Lake Inn
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (46)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
$575 nightly
The price is $639
Jul 10 - Jul 11
Total includes taxes and fees
The Fern Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find out more about Chestertown

Find out more about Chestertown

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

Frequently asked questions

Searching for romantic hotels in Chestertown?
If you and your partner need a romantic escape, we've got just the thing. Our guests also enjoy Chestertown for its lakeside setting. You might consider checking out some of the nearby sights and attractions such as Loon Lake Beach, Friends Lake, or Loon Lake. If you're interested in staying near a certain attraction, you can sort by neighborhood or distance to top sights, so you'll be able to see everything on your list.
What's the best hotel for a romantic getaway to Chestertown?
Friends Lake Inn is a favorite 4-star hotel for couples, and features a full-service spa and wedding services. Another good option for a romantic stay is The Fern Lodge.
How many romantic hotels are there in Chestertown?
Expedia has 12 romantic Chestertown hotels for you both to enjoy.
When is the best time of year for a romantic getaway to Chestertown?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chestertown: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What is there to do in Chestertown?
There's nothing better than experiencing a new destination with your sweetheart, so consider checking out all that Chestertown has to offer. Couples looking to get out in nature will enjoy Chestertown for its lakeside setting. If you want to spend a day exploring, you might consider a stop at Loon Lake Beach, Friends Lake, or Loon Lake.
What's the best way to get to Chestertown and around town during my romantic getaway?
These transportation options in Chestertown might help your romantic getaway go off without a hitch: Make your way to Chestertown with a flight to Glens Falls, NY (GFL-Floyd Bennett Memorial), which is the closest major airport located 23.6 mi (38 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.