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Find Romantic Hotels in Chestertown, NY

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Check availability on Chestertown Romantic Hotels

Tonight
2 Dec - 3 Dec
Tomorrow
3 Dec - 4 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Chestertown Romantic Hotels

Lake view
The Fern Lodge

The Fern Lodge

3.5 star property
Chestertown
9.8 out of 10, Exceptional, (50)
"Absolutely beautiful "
United States
Dana
The Fern Lodge
Lobby
The Queensbury Hotel

The Queensbury Hotel

3.0 star property
Glens Falls
9.4 out of 10, Exceptional, (1451)
"We loved our stay here!!! "
United States
Joseph
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
Silver Bay
8.8 out of 10, Excellent, (136)
"Awesome place"
United States
Kevin
The price is SAR 368
SAR 408 total
includes taxes & fees
1 Jan - 2 January 2026
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
Lake George
8.4 out of 10, Very Good, (1004)
"Clean room great customer service and the grounds were great for the Lake"
United States
ROBERT
The price is SAR 471
SAR 594 total
includes taxes & fees
3 Dec - 4 Dec
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
Hague
9.8 out of 10, Exceptional, (18)
"Very friendly owner and beautiful views"
United States
Anthony
The price is SAR 561
SAR 717 total
includes taxes & fees
15 Dec - 16 Dec
Trout House Village Resort
Interior
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

North River
10.0 out of 10, Exceptional, (93)
"Cabin was very well done, clean- bed was super comfortable! The view of the mountains was fantastic- great for star watching too!"
United States
millie h.
The price is SAR 619
SAR 904 total
includes taxes & fees
10 Dec - 11 Dec
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Interior
RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR

RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR

North River
9.2 out of 10, Wonderful, (63)
"Bird Camp is nestled on a beautiful and peaceful hobby farm. The camp is well maintained and very cozy. We had a wonderful time and we are looking forward to our next stay here!"
United States
Zacchary B.
The price is SAR 657
SAR 999 total
includes taxes & fees
3 Dec - 4 Dec
RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR
Outdoor dining
Handcrafted mountain cabin with gorgeous views

Handcrafted mountain cabin with gorgeous views

North River
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 SAR 638
SAR 929 total
includes taxes & fees
3 Dec - 4 Dec
Handcrafted mountain cabin with gorgeous views
Outdoor dining
Camp Lillian Gorgeous New Cabin with Mountain Views

Camp Lillian Gorgeous New Cabin with Mountain Views

North River
9.8 out of 10, Exceptional, (77)
"Just what we were looking for. Beautiful and peaceful. "
United States
Lisa S.
The price is SAR 600
SAR 883 total
includes taxes & fees
3 Dec - 4 Dec
Camp Lillian Gorgeous New Cabin with Mountain Views
Interior
Beautiful cottage on scenic Adirondack hobby farm

Beautiful cottage on scenic Adirondack hobby farm

North River
9.6 out of 10, Exceptional, (60)
"We had a lovely overnight stay. Enjoyed the hot tub, the thoughtfully designed cabin, scenic views, and Thirteenth Lake. Leslie is a fun and thoughtful host."
United States
Anya B.
The price is SAR 563
SAR 833 total
includes taxes & fees
3 Dec - 4 Dec
Beautiful cottage on scenic Adirondack hobby farm
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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Top Chestertown Hotel Reviews

Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Friendly staff, wonderful food, beautiful lake views, nice amenities. "
Kelly 2-night trip
Posted 4 days ago
Fort William Henry Hotel and Conference Center

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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.