Photo by Julie Miller

Search Lakeside Hotels in Chestertown

Most hotels are fully refundable. Because flexibility matters.

Save 10% or more on select stays with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Top Chestertown Lakeside Hotels

The Fern Lodge
3.5 out of 5
46 Fiddlehead Bay Rd., Chestertown, NY, 12817
The price is Rs42,657 per night from 4 Jul to 5 Jul
4.9/5 Exceptional! (26 reviews)
"I would highly recommend The Fern Lodge. The is amazing. My husband describes it as a peaceful place. And it’s extremely clean. Sharon is great! She gave us a tour. We will definitely be back!!"

Reviewed on 14 Aug 2020

The Fern Lodge
Pine Tree Motel & Cabins
2 out of 5
5537 State Route 8, Chestertown, NY, 12817
The price is Rs12,927 per night from 29 Jun to 30 Jun
4.5/5 Wonderful! (91 reviews)
Cozy and Cute lodgings.
"Cozy, cute and clean lodgings. Owner was super friendly and beds were comfy. My daughter and I stayed here for a quick overnight. It’s conveniently located and set back off of Rt 8 in Chestertown. We had a quiet and restful stay."

Reviewed on 12 Oct 2021

Pine Tree Motel & Cabins
Friends Lake Inn
4 out of 5
963 Friends Lake Rd, Chestertown, NY, 12817
The price is Rs13,240 per night from 28 Jun to 29 Jun
4.4/5 Wonderful! (59 reviews)
"We enjoyed everything about the property, especially the sauna. Staff is amazing especially Nicole, very vibrant and lively. Will definitely be back again."

Reviewed on 10 Apr 2022

Friends Lake Inn
Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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.

Chestertown Hotel Reviews
expedia verified reviews

Plan your trip in a snap on the app

From home or hammock, organise your entire escape and explore app offers

Text yourself a download link for easy access

By providing your number, you agree to receive a one-time automated text message with a link to get the app. Standard text message rates may apply.
QR code