Photo by Julie Miller

Find Romantic Hotels in Chestertown from S$317

    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
26 Jul - 27 Jul
Tomorrow
27 Jul - 28 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

Top Romantic Hotels in Chestertown

Friends Lake Inn
1 bedroom, premium bedding, individually decorated

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (90)
"Quiet lodging and friendly staff"
The price is S$317
includes taxes & fees
27 Jul - 28 Jul
Friends Lake Inn
The Fern Lodge
Lake view

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
"A really great old school hotel from days gone by upgraded to modern standards. Pool and hot tub were great. Easy parking and right in the downtown. "
Randolph S 1-night trip
Posted 2 days ago
The Queensbury Hotel

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.
What's the best hotel for couples in Chestertown?
Friends Lake Inn is a favourite 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 will we be able to find 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, 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.