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Find Romantic Hotels in Chestertown, NY from $99

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Check availability on Chestertown Romantic Hotels

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Oct 25 - Oct 26
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Oct 26 - Oct 27
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Oct 31 - Nov 2
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Nov 7 - Nov 9

Top Chestertown Romantic Hotels

Premier Room | 1 bedroom, premium bedding, individually decorated
Friends Lake Inn
Friends Lake Inn
4.0 star property
8.6 out of 10, Excellent, (102)
"Staff was great. The inn is unique. Perfect!"
United States
Linda
$258 nightly
The price is $287
Nov 7 - Nov 8
Total with taxes and fees
Friends Lake Inn
Lake view
The Fern Lodge
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (49)
"Absolutely beautiful "
United States
Dana
$478 nightly
The price is $531
Oct 27 - Oct 28
Total with taxes and fees
The Fern Lodge
Lobby
The Queensbury Hotel
The Queensbury Hotel
3.0 star property
9.4 out of 10, Exceptional, (1388)
"Great place to stay. "
United States
Sandra
$104 nightly
The price is $115
Nov 12 - Nov 13
Total with taxes and fees
The Queensbury Hotel
Private beach, beach volleyball, sailing, kayaking
Silver Bay YMCA Inn and Conference Center
Silver Bay YMCA Inn and Conference Center
3.0 star property
8.8 out of 10, Excellent, (130)
"Awesome place"
United States
Kevin
$89 nightly
The price is $99
Oct 27 - Oct 28
Total with taxes and fees
Silver Bay YMCA Inn and Conference Center
Aerial view
Fort William Henry Hotel and Conference Center
Fort William Henry Hotel and Conference Center
3.0 star property
8.4 out of 10, Very Good, (1004)
"a very nice place to stay"
United States
william
$137 nightly
The price is $152
Nov 6 - Nov 7
Total with taxes and fees
Fort William Henry Hotel and Conference Center
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services
Trout House Village Resort
Trout House Village Resort
3.0 star property
9.8 out of 10, Exceptional, (17)
"Beautiful views and wonderful staff. Provides an atmosphere for activities and relaxation while being able to access anywhere on the lake."
United States
John
$189 nightly
The price is $210
Oct 27 - Oct 28
Total with taxes and fees
Trout House Village Resort
Interior
GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM
GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM
9.8 out of 10, Exceptional, (41)
"Been here several times and happily keep going back. Such an amazing niche this place is. We also kayaked on 13th lake while here"
United States
Denise K.
$159 nightly
The price is $176
Oct 31 - Nov 1
Total with taxes and fees
GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM
Interior
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
10.0 out of 10, Exceptional, (92)
"Great location beautiful view and very nice cabin thank you!"
United States
Aline B.
$246 nightly
The price is $273
Oct 27 - Oct 28
Total with taxes and fees
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Outdoor dining
Camp Lillian Gorgeous New Cabin with Mountain Views
Camp Lillian Gorgeous New Cabin with Mountain Views
9.8 out of 10, Exceptional, (74)
"The Lillian cabin was great!! It was not only beautifully made but it had everything we needed including a peaceful and quiet two nights in the Adirondacks!!"
United States
robert
$212 nightly
The price is $235
Nov 2 - Nov 3
Total with taxes and fees
Camp Lillian Gorgeous New Cabin with Mountain Views
Property grounds
Handcrafted mountain cabin with gorgeous views
Handcrafted mountain cabin with gorgeous views
9.8 out of 10, Exceptional, (49)
"Lovely little cabin tucked away near many hiking trails and the cute town of North Creek. Thanks so much!"
United States
Aileen T.
$229 nightly
The price is $254
Oct 27 - Oct 28
Total with taxes and fees
Handcrafted mountain cabin with gorgeous views
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.
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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

Top Chestertown Hotel Reviews

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"Although only for one night, we looked forward to our stay at this "boutique" hotel. The property turned out to be larger than we expected, but pleasant. The staff were universally cheerful, helpful, and informative - especially at the front desk. Our room was very large and comfortable, although the walls were varying shades of (battleship) grey and the furniture blocky and institutional. We see an opportunity for creative, colorful redecoration. The bathroom was cute/ small/ clean. Would benefit from an additional shelf to put our bathroom kits. Our 3rd floor room overlooked another roof so a higher floor would likely have a better view. We had breakfast in the elegant dining room, where we were able to apply our $20 VIP coupon to a delicious meal. All-in-all an enjoyable and restful stay."
Thomas 1-night trip
Posted 1 day ago
The Queensbury Hotel

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.
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.

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