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Find Romantic Hotels in Chestertown, NY

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Check availability on Chestertown Romantic Hotels

Tonight
Jun 29 - Jun 30
Tomorrow
Jun 30 - Jul 1
Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13

Top Chestertown Romantic Hotels

The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (46)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The Fern Lodge
Trout House Village Resort
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (11)
"Absolutely wonderful place and super friendly staff "
The price is ₩341,002
₩412,539 total
includes taxes & fees
Jul 6 - Jul 7
Trout House Village Resort
The Queensbury Hotel
Lobby

The Queensbury Hotel

3.0 star property
9.2 out of 10, Wonderful, (1254)
"Beautiful hotel!"
The Queensbury Hotel
The Villas on Lake George
Property grounds

The Villas on Lake George

2.5 star property
7.6 out of 10, Good, (81)
"Great place for family get away . Beautiful location lake front beach and the pool. Our tradition every year to visit Lake George "
The price is ₩2,245,766
₩2,492,800 total
includes taxes & fees
Jul 26 - Jul 27
The Villas on Lake George
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.

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.
What's the best hotel for a romantic getaway to Chestertown?
Friends Lake Inn is a favorite 4-star hotel for couples, and features a full-service spa and wedding services. Another good option for a romantic stay is The Fern Lodge.
How many romantic hotels are there in Chestertown?
Expedia has 12 romantic Chestertown hotels for you both to enjoy.
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.