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Search Motels in Chestertown

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Check prices for these dates

Compare Motels in Chestertown with updated reviews, rates, and availability.

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (86)
"Quiet lodging and friendly staff"
The price is SARĀ 836
SARĀ 928 total
includes taxes & fees
13 Feb - 14 Feb
Friends Lake Inn

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (45)
"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 price is SARĀ 2,179
SARĀ 2,418 total
includes taxes & fees
18 Feb - 19 Feb
The Fern Lodge

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

10.0 out of 10, Exceptional, (27)
"My family and friends would like to thank Tony and Kristi (the owners) for such a great vacation at their home in Chestertown. Everything on the description of the house was accurate. The house was super cozy and comfortable. It was clean and ready for us when we arrived. The owners were helpful with a few questions we had early in our stay and quick to respond. We brought our furry buddy Willow with us, and we are pretty sure she did not want to leave. There was plenty of room for her to...
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

1970s acreage surrounded by trees with deck, grill, & internet

8.0 out of 10, Very Good, (2)
"Our family booked a 2-night stay for a ski trip for President's Weekend. What mattered to us the most was cleanliness and comfort of a home as we were looking to cook dinners in the property (i.e., we were focused on a property with a full kitchen, grill, woodstove, etc.). 1. The property was generally clean and charming ("rustic", as advertised!) and we were impressed upon entering. Check-in was very easy. 4-5 star experience! 2. Unfortunately the charm wore off quickly as we noticed a...
1970s acreage surrounded by trees with deck, grill, & internet

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
"very friendly and helpful owners. rooms were very clean and comfortable. good location as well"
Pine Tree Motel & Cabins

The Loft at The Remington

3.5 star property
The Loft at The Remington

Stock Farm, an Adirondack Gem

Stock Farm, an Adirondack Gem
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.
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Other property types in Chestertown

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (106)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
Eagles Nest at Loon Lake near Gore Mountain

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Lakefront cabin with beautiful loft, game room, views, private dock

9.2 out of 10, Wonderful, (35)
"Loved everything from the coffee maker to the views at this place. Fantastic!"
Lakefront cabin with beautiful loft, game room, views, private dock
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.

Frequently asked questions

What can I expect from a motel trip to Chestertown?
If youā€™re having a hard time finding motels in Chestertown, consider some of the motels we suggest around the area or let Expedia help you find a similar property from over 116 hotels and other lodging options. Simply use our search tools to filter by price per night or cost-effective amenities such as free breakfast and free airport transportation.
What's it like to stay in a motel?
At most motels, youā€™ll often find an outdoor pool and free parking. When you stay at a motel, youā€™ll usually access your room directly from the parking lot. The word ā€œmotelā€ was coined in 1925 by the owner of the Milestone Mo-Tel in San Luis Obispo, California.
What are the best motels in Chestertown?
Here youā€™ll find some of Expedia customersā€™ favorite motels in the larger area. Super 8 by Wyndham Queensbury Glen Falls, Lake George Area is located 25.3 mi (40.7 km) from the heart of Chestertown. Enjoy access to the 24-hour front desk, and freebies including breakfast, WiFi, and parking. Super 8 by Wyndham Lake George/Warrensburg Area: A 24-hour front desk along with freebies like breakfast, WiFi, and parking are available during your stay. Central Chestertown is 11.7 mi (18.8 km) away. Maple Leaf Motel: Enjoy access to the golf course, and freebies including WiFi and parking. Located 14.2 mi (22.9 km) from the heart of Chestertown. Howard Johnson by Wyndham Lake George: Central Chestertown is 16.6 mi (26.6 km) away. Free WiFi, free parking, and a 24-hour front desk are available during your stay. Mohican Resort Motel: 20.1 mi (32.3 km) from the heart of Chestertown. Enjoy access to the fitness center, and freebies including WiFi and parking.
What things can I to do in Chestertown?
Those whoā€™ve visited Chestertown like the lakeside. As youā€™re sightseeing around the area, be sure to enjoy all there is to see and do. These are some of the parks and outdoorsy places: Loon Lake Beach, Friends Lake, and Loon Lake. Youā€™ll find these family-friendly sights in the area: Garnet Hill Lodge and Ski Resort, House of Frankenstein Wax Museum, and Dr. Morbidā€™s Haunted House. Other places worth a visit include Hudson River and Tripp Pond.
What's the weather like in Chestertown?
Weather can make or break a roadtrip, so hereā€™s some data about year-round temperatures in Chestertown to help you plan yours: The hottest months are usually July and August with an average temp of 65Ā°F, while the coldest months are January and February with an average of 25Ā°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What are my options for getting around Chestertown when staying in a motel?
Weā€™ve gathered some information about local transportation options in Chestertown to help you navigate your stay: Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) away from the heart of the city. If youā€™d like to venture out around the area, you may want to rent a car for your trip.