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

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Check availability on Chestertown Romantic Hotels

Tonight
Aug 15 - Aug 16
Tomorrow
Aug 16 - Aug 17
Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

Top Chestertown Hotel Reviews

Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent
"So much outdoor space. Staff was excellent, especially Jay."
Samson 1-night trip
Posted 4 hours ago
Baymont by Wyndham Queensbury / Lake George
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

10/10 Excellent
"This is a great motel to stay in in Lake George. We walked to the center of Lake George where all the restaurants and cafes and ice cream shops are...just a few minutes walk. I think being at the end of town, makes it much quieter, which is nice. The parking was easy, right outside our room. The room was very clean, had plenty of towels and the shower was amazing! We did not use the pool so cannot comment on that. The young lady at check in was very polite and gave us suggestions on a coffee shop in the am. Check-in was easy and we left before the front desk was open, but you can just drop your key and go and then receive a text that confirmed our departure. Would definitely stay here again."
Catherine 1-night trip
Posted 6 hours ago
Adirondack Retreat Inn & Suites
Courtyard by Marriott Lake George

Courtyard by Marriott Lake George

10/10 Excellent
"Clean, friendly, and very easy access to parking, pool, and bike week event!"
Blanca 3-night trip
Posted 9 hours ago
Courtyard by Marriott Lake George
Tiki Resort

Tiki Resort

10/10 Excellent
"Enjoyed our stay in the renovated rooms. Outdoor pool was very enjoyable and loved the overall location,"
Stephanie 2-night trip
Posted 12 hours ago
Tiki Resort
The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"We have stayed here at least 5 times Everyone is friendly and kind Newly decorated celebrating their 100th anniversary Truly a great place with a lot of history"
Annette 1-night trip
Posted 12 hours ago
The Queensbury Hotel
Scotty's Lakeside Resort

Scotty's Lakeside Resort

8/10 Good
"The property along with the amenities are the nicest on the strip,however the rooms are small And outdated. The rooms are not cleaned everyday, the staff provided new towels every day but did not make the beds everyday."
melissa 5-night trip
Posted 1 day ago
Scotty's Lakeside Resort
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

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

8/10 Good
"Our family enjoyed both the indoor and outdoor pools. The indoor pool was very ideal, especially because it rained a couple of days therefore my kids didn’t miss out. The staff was very friendly and helpful. As per the breakfast, they have a variety of food which is good when you have picky eaters but the eggs could have been better cooked. The rooma are very clean. I think the only negative thing I can say is that the staff forgot to clean out my garbage one day but the next day everything was intact."
Leonardo 3-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

10/10 Excellent
"Very family friendly. Easy check in, friendly staff. Love the pools and mountain views."
Mary 1-night trip
Posted 3 days ago
Holiday Inn Resort Lake George - Adirondack Area by IHG

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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