A waterfront town with a pier, dock, and several buildings.

Find Romantic Hotels in Chestertown, NY

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Check availability on Chestertown Romantic Hotels

Tonight
Aug 17 - Aug 18
Tomorrow
Aug 18 - Aug 19
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Top Chestertown Hotel Reviews

Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

8/10 Good
"Bon choix d’hôtel avec les enfants ! Salle de jeux, piscine, module extérieur, activités. Les enfants ne s’ennuient pas ! Hôtel bien situé ! La salle de bain aurait besoin d’être rafraîchi."
Sarah 1-night trip
Posted less than an hour ago
Holiday Inn Resort Lake George - Adirondack Area by IHG
The Georgian Lakeside Resort

The Georgian Lakeside Resort

8/10 Good
"It’s a nice motel and it’s right on the lake which is great. The room was nice. Had some minor issues with broken molding in the bathroom and an AC system which needs an upgrade. Overall we liked the motel and would go back there."
John 2-night trip
Posted 12 hours ago
The Georgian Lakeside Resort
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

10/10 Excellent
"Needs a bigger microwave but, after that everything was excellent."
Orlando 2-night trip
Posted 12 hours ago
Adirondack Retreat Inn & Suites
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

8/10 Good
"Nothing"
Chadli 2-night trip
Posted 15 hours ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Tiki Resort

Tiki Resort

10/10 Excellent
"staff is great, location is great"
Marc 3-night trip
Posted 16 hours ago
Tiki Resort
Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

8/10 Good
"The stay was not bad at all."
Tiara 2-night trip
Posted 1 day ago
Baymont by Wyndham Queensbury / Lake George

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 Friends Lake, Loon Lake, or Hudson River. 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 Friends Lake, Loon Lake, or Hudson River.
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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