Chestertown Holidays

Photo by Julie Miller

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Chestertown Beach Holiday

Escape the stresses of daily life and let your body, mind and soul completely relax during your Chestertown holiday. Few things are more invigorating than the cool sea breeze and the soothing sound of waves lapping at the shore. Organise your trip to Chestertown the quick and easy way by locking in one of our Chestertown holiday deals. Many visitors opt to base themselves near Loon Lake Beach, a must-see only 3 kilometres from the downtown area.

Top hotels in Chestertown

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8, Chestertown, NY
The price is S$248 per night from 21 Sept to 22 Sept
S$248
21 Sept - 22 Sept
includes taxes & fees
9.2/10 Wonderful! (140 reviews)
"Came here for the weekend with my husband and my dog! The place is really nice, clean"

Reviewed on 2 Sept, 2025

Pine Tree Motel & Cabins
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd, Chestertown, NY
The price is S$316 per night from 19 Sept to 20 Sept
S$316
19 Sept - 20 Sept
includes taxes & fees
8.6/10 Excellent! (100 reviews)
"Staff was great. The inn is unique. Perfect!"

Reviewed on 7 Sept, 2025

Friends Lake Inn
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St, Glens Falls, NY
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,353 reviews)
"Beautiful 1920s restored hotel in a very clean and safe City of Glen Falls."

Reviewed on 15 Sept, 2025

Get rates
The Queensbury Hotel
See all 1,551 properties in Chestertown
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.