Chestertown Holiday Rentals - Holiday Homes in Chestertown

Q: Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

Q: How many vacation rentals will I find in Chestertown?

With 62 Expedia vacation rentals, you're sure to find just the right place for your Chestertown stay.

Q: What’s there to see and do in Chestertown?

Friends Lake and Loon Lake are a couple of lovely local spots to get outside and enjoy nature. Hudson River and Loon Lake Beach are other places to visit while you're in town.

Q: What’s a vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.

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In two weeks

In two months

In three months

In four months

Our top choices for Chestertown vacation rentals

A lakeside cabin with a wooden deck and a view of the lake.

1. Trout House Village Resort

Hague

Matthew

P8,794 total

includes taxes & fees

Oct 20 - Oct 21

A sandy beach with a calm lake, trees, and a distant hill.

2. Schroon Lake Room < 1 Mi to Marina & Beach!

Schroon Lake

Kevin

P10,606 total

includes taxes & fees

Sep 27 - Sep 28

A poolside area with a wooden deck, a grill, and a flower planter.

3. Lincoln Log Colony

Lake George

David

P8,089 total

includes taxes & fees

Sep 30 - Oct 1

A landscaped garden with a fountain, flags, and a view of a body of water.

4. Walk to Schroon Lake! Studio w/ Shared Fire Pit

Schroon Lake

P10,606 total

includes taxes & fees

Oct 5 - Oct 6

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Top Chestertown Hotel Reviews

Courtyard by Marriott Lake George

10/10 Excellent

"Helpful staff"

Pine Tree Motel & Cabins

8/10 Good

"Charming old fashion Adirondack rustic style / decor individual small cabins (also has motel-styled rooms) - parking either in front of rooms or between cabins, a couple of minutes outside Chestertown, NY, 30 minutes from Schroon Lake, and 45 minutes from Ticonderoga (StarTrek Museum & Fort). Very nice, friendly, and accomidating owners / operators. Breakfast / coffee place "Two Sparrows" 5 minutes down the road. Driveway very well lite / marked at night, although wish those lights had either dimmed or turned off post midnight for a better / darker sleep . . . As it was a very wet / rainy, and cold night - heat worked very qickly / well and found extra pillows and blanket. Plenty of hot water in sink / shower, soap, shampoo, small college refrigerator and microwave provided, however no hairdryer for partner . . . Did not test WiFi as we only stayed for 8 hours total time. Would have wished to have had more time to explore grounds and Chestertown itself."

Surfside On The Lake

10/10 Excellent

"The property was very well maintained and the room was also well maintained and clean. The reservation stated a view of the lake and it was a partial view which I expected. Overall...Nice. The reason I'm writing this review is to what happened on the 1st night/early morning of our stay. Around 5am the fire alarm woke us up! We could smell burning (plastic?) no smoke yet, but proceeded to evacuate the building. We waited outside for First Responders after my husband and the staff called 911. After they arrived, extinguished the fire, and cleared the building, Kris from the office found us and apologized. She let us know that the room would be "comped" for the night and set us up in a different building with an even better room. The rest of our stay was wonderful. We loved the new room better than the one that we originally booked! Thanks Kris!! When we make reservations to return to the Surfside next year....we will definitely be booking the better room, funny how things work out😊 Thanks again M. Bonestell"

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chestertown!

Frequently asked questions

Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

How many vacation rentals will I find in Chestertown?

With 62 Expedia vacation rentals, you're sure to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

Friends Lake and Loon Lake are a couple of lovely local spots to get outside and enjoy nature. Hudson River and Loon Lake Beach are other places to visit while you're in town.

What’s a vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.

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