TOP Romantic Hotels in Chestertown, NY for 2026

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

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Top Chestertown Hotel Reviews

Adirondack Retreat Inn & Suites

8/10 Good

"The hotel is very well located, and the price-to-value ratio is excellent. The room was clean and comfortable, and the front desk staff was very friendly and helpful. The only minor inconvenience was the parking. The parking area was quite full, so we had to park in a spot that was a little far from our room. However, the parking was still within the hotel property, so it was not a major issue. Overall, we had a very pleasant stay and would definitely consider staying here again."

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent

"It was clean and the bed was very comfy"

Frequently asked questions

Searching for romantic hotels in Chestertown?

If you and your partner need a romantic escape, we'd like to help you plan for it. 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 close to a certain attraction, you can sort properties by neighbourhood or distance to top sights, so you and your partner will get 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, take a look at these details about year-round temperatures in Chestertown: The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm of snowfall.

What is there to do in Chestertown?

There's nothing better than seeing 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 stopping 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 trip 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 centre. If you'd like to explore around the area, consider renting a car to explore more sights.

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