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Find Romantic Hotels in Chestertown, NY

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Top Chestertown Romantic Hotels

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
The price is AED 949
AED 1,054 total
includes taxes & fees
8 Nov - 9 Nov
Friends Lake Inn
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (49)
"Comfortable, friendly, beautiful lodge, spacious facilities"
Canada
Frederick
The Fern Lodge
The Queensbury Hotel
3.0 star property
9.4 out of 10, Exceptional, (1387)
"Great place to stay. "
United States
Sandra
The Queensbury Hotel
Silver Bay YMCA Inn and Conference Center
3.0 star property
8.8 out of 10, Excellent, (129)
"Awesome place"
United States
Kevin
The price is AED 328
AED 364 total
includes taxes & fees
26 Oct - 27 Oct
Silver Bay YMCA Inn 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
The price is AED 384
AED 496 total
includes taxes & fees
6 Nov - 7 Nov
Fort William Henry Hotel and Conference Center
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
The price is AED 550
AED 702 total
includes taxes & fees
27 Oct - 28 Oct
Trout House Village Resort
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.
The price is AED 474
AED 648 total
includes taxes & fees
31 Oct - 1 Nov
GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM
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.
The price is AED 698
AED 1,003 total
includes taxes & fees
26 Oct - 27 Oct
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN 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.
The price is AED 643
AED 934 total
includes taxes & fees
26 Oct - 27 Oct
Handcrafted mountain cabin with gorgeous 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
The price is AED 588
AED 864 total
includes taxes & fees
2 Nov - 3 Nov
Camp Lillian Gorgeous New Cabin with Mountain 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.

Top Chestertown Hotel Reviews

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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.