Photo by Julie Miller

Find Romantic Hotels in Chestertown, NY

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Romantic Hotels

Tonight
Jul 25 - Jul 26
Tomorrow
Jul 26 - Jul 27
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Top Chestertown Romantic Hotels

Friends Lake Inn
Relax in this inviting bedroom with a large bed, stone fireplace, and mounted TV.

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (90)
"Quiet lodging and friendly staff"
The price is ￥32,800
￥36,408 total
includes taxes & fees
Jul 27 - Jul 28
Friends Lake Inn
The Fern Lodge
Relax by the water's edge in this serene outdoor seating area, complete with a fire pit and comfortable seating.

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (47)
"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
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.

Top Chestertown Hotel Reviews

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"Those of us older than 60 often wish for service without the slightly noticeable attitude of the younger generation that does occur at times. Not always. We had a mix here and overall a very pleasant and enjoyable experience. The bartender went out of his way to make my drink (had to substitute one ingredient), and came over to check to see if I was happy- I was!"
Russell 1-night trip
Posted 5 hours ago
The Queensbury Hotel

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.
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 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.