Photo by Julie Miller

Find Romantic Hotels in Chestertown, NY

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Romantic Hotels

Tonight
5 Aug - 6 Aug
Tomorrow
6 Aug - 7 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Chestertown Romantic Hotels

We don't have any properties that match your exact search

Recommended hotels in Chestertown

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, (94)
"Very nice location. Would have enjoyed more activity like hiking or a pool or something on site. But it met our requirements for a beautiful place to stay with good food"
The price is £186
includes taxes & fees
7 Aug - 8 Aug
Friends Lake Inn
Pine Tree Motel & Cabins
Cabins with front porches and lawns set amidst dense coniferous trees.

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (133)
"Excellent location and staff was very friendly."
The price is £146
includes taxes & fees
17 Aug - 18 Aug
Pine Tree Motel & Cabins
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
Charming 2-bedroom cabin in welcoming Chestertown with Lake Views and WiFi
Cozy cabin interior with a stone fireplace, wooden beams, and a sloped ceiling.

Charming 2-bedroom cabin in welcoming Chestertown with Lake Views and WiFi

The price is £496
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom cabin in welcoming Chestertown with Lake Views and WiFi
Lakefront Rustic 1930s dog friendly Cabin w/lg screened porch near Lake George
Cozy cabin interior with a dining table, bench, and wicker chair.

Lakefront Rustic 1930s dog friendly Cabin w/lg screened porch near Lake George

10.0 out of 10, Exceptional, (27)
"Amazing view, so peaceful and relaxing! The hosts were fantastic"
The price is £413
includes taxes & fees
4 Sept - 5 Sept
Lakefront Rustic 1930s dog friendly Cabin w/lg screened porch near Lake George
Silver Bay YMCA Inn and Conference Center
Enjoy a leisurely swim in the calm waters, surrounded by a lifeguard tower and scenic views.

Silver Bay YMCA Inn and Conference Center

3.0 star property
8.6 out of 10, Excellent, (101)
"Beautiful area , very close to the lake . "
The price is £114
includes taxes & fees
10 Aug - 11 Aug
Silver Bay YMCA Inn and Conference Center
Trout House Village Resort
Cozy cabin interior with a stone fireplace, dining area, and comfortable seating.

Trout House Village Resort

3.0 star property
9.8 out of 10, Exceptional, (12)
"Absolutely wonderful place and super friendly staff "
The price is £138
includes taxes & fees
2 Sept - 3 Sept
Trout House Village Resort
The Queensbury Hotel
Experience the classic charm of Maple Street, where a grand fireplace, elegant chandelier, and checkered floor create a sophisticated atmosphere.

The Queensbury Hotel

3.0 star property
9.2 out of 10, Wonderful, (1310)
"Lovely historic hotel in lovely Glens Falls"
The Queensbury Hotel
Days Inn by Wyndham Queensbury/Lake George
Two single beds with matching headboards and pillows, each covered in a patterned bedspread, are accompanied by a nightstand with a lamp.

Days Inn by Wyndham Queensbury/Lake George

2.0 star property
5.8 out of 10, (1008)
"The property was working on improvements while we were there, which is great to see that they are continuously working on providing an accommodating place. We would stay here again. Thank you for your time. "
The price is £55
includes taxes & fees
2 Sept - 3 Sept
Days Inn by Wyndham Queensbury/Lake George
Red Roof Inn Queensbury
In-room safe, desk, laptop workspace, blackout curtains

Red Roof Inn Queensbury

2.5 star property
7.0 out of 10, Good, (1006)
"Just an average hotel, a place to stay nothing fancy nothing extra. If you need a place to sleep and nothing else then this place is fine. "
The price is £87
includes taxes & fees
2 Sept - 3 Sept
Red Roof Inn Queensbury
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

Tiki Resort

Tiki Resort

10/10 Excellent
"The sorroundings are good: the reception area offers excellent costumer service.THANK YOU . The ceilings,carperts,wall, bathroom need up grade assap. There is a strong , mustly smell .. PAY ATTENTION ..You have excellent location) Everything else is Fine."
Javier 2-night trip
Posted 9 hours ago
Tiki Resort

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.