A waterfront town with a pier, dock, and several buildings.

Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Chestertown vacation rentals

Cottage (2 Bedrooms) | Interior

1. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
3.0 star property
Warrensburg
The price is NT$6,492
NT$12,556 total
includes taxes & fees
Sep 17 - Sep 18
Adirondack Mountains Cottage Near Gore Mountain!
Cabin, 1 Bedroom, Non Smoking, Lake View

2. Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.6 out of 10, Exceptional, (25 reviews)
"It was a great place, clean rooms, nice environment, cabins, family friendly, right on lake"
United States
Matthew
The price is NT$4,185
NT$5,432 total
includes taxes & fees
Sep 13 - Sep 14
Trout House Village Resort
Room

3. Lake George Escape - Campground

Lake George Escape - Campground
2.0 star property
Diamond Point
8.4 out of 10, Very Good, (204 reviews)
"Love coming here each year."
United States
Kristen
The price is NT$5,170
NT$5,739 total
includes taxes & fees
Sep 21 - Sep 22
Lake George Escape - Campground
Exterior

4. Lincoln Log Colony

Lincoln Log Colony
2.0 star property
Lake George
9.0 out of 10, Wonderful, (20 reviews)
"The grounds are very well kept. The cottage we stayed in was nice. It has a smell but was quite clean and there is one air conditioner to the whole cottage it worked well as long as the bedroom doors stayed open."
United States
David
The price is NT$4,282
NT$4,753 total
includes taxes & fees
Sep 16 - Sep 17
Lincoln Log Colony
Sports facility

5. The Elms Waterfront Cottages

The Elms Waterfront Cottages
2.5 star property
Lake Luzerne
8.6 out of 10, Excellent, (20 reviews)
"The kids had fun using the rowboat and paddle boats. The staff was very friendly and helpful."
United States
Colleen
The price is NT$9,912
NT$11,002 total
includes taxes & fees
Sep 23 - Sep 24
The Elms Waterfront Cottages
Apartment (0 Bedroom) | Interior

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

Walk to Schroon Lake! Studio w/ Shared Fire Pit
3.0 star property
Schroon Lake
The price is NT$4,349
NT$5,350 total
includes taxes & fees
Sep 13 - Sep 14
Walk to Schroon Lake! Studio w/ Shared Fire Pit
Apartment (0 Bedroom) | Interior

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

Schroon Lake Room < 1 Mi to Marina & Beach!
3.0 star property
Schroon Lake
10.0 out of 10, Exceptional, (1 review)
"Clean, comfortable room. Very friendly and welcoming hosts."
United States
Kevin
The price is NT$4,342
NT$5,342 total
includes taxes & fees
Sep 17 - Sep 18
Schroon Lake Room < 1 Mi to Marina & Beach!
Apartment (0 Bedroom) | Interior

8. Cozy Room Near Schroon Lake Marina, Town & Beach!

Cozy Room Near Schroon Lake Marina, Town & Beach!
3.0 star property
Schroon Lake
6.0 out of 10, (2 reviews)
"Help!! We didn’t stay at this property due to the property stating it was lakefront and marina. The property was in complete disrepair condition. Junk cars, high weeds, room smelled of smoke. I would request a refund."
United States
Pamela
The price is NT$4,349
NT$5,350 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Room Near Schroon Lake Marina, Town & Beach!
Apartment (0 Bedroom) | Interior

9. Close to Marina, Beach & Town! Schroon Lake Escape

Close to Marina, Beach & Town! Schroon Lake Escape
3.0 star property
Schroon Lake
The price is NT$4,349
NT$5,350 total
includes taxes & fees
Sep 13 - Sep 14
Close to Marina, Beach & Town! Schroon Lake Escape
Apartment (0 Bedroom) | Interior

10. Easy Schroon Lake Living! Close to Marina & Town

Easy Schroon Lake Living! Close to Marina & Town
3.0 star property
Schroon Lake
The price is NT$4,349
NT$5,350 total
includes taxes & fees
Sep 13 - Sep 14
Easy Schroon Lake Living! Close to Marina & Town
Apartment (0 Bedroom) | Interior

11. Boat, Fish & Hike! All-season Schroon Lake Getaway

Boat, Fish & Hike! All-season Schroon Lake Getaway
3.0 star property
Schroon Lake
The price is NT$4,349
NT$5,350 total
includes taxes & fees
Sep 14 - Sep 15
Boat, Fish & Hike! All-season Schroon Lake Getaway
Apartment (0 Bedroom) | Interior

12. < 1 Mi to Boat Launch! Schroon Lake Basecamp

< 1 Mi to Boat Launch! Schroon Lake Basecamp
3.0 star property
Schroon Lake
The price is NT$5,704
NT$6,882 total
includes taxes & fees
Sep 13 - Sep 14
< 1 Mi to Boat Launch! Schroon Lake Basecamp
Apartment (0 Bedroom) | Interior

13. Walk to Main St & Schroon Lake! Cozy Upstate Gem

Walk to Main St & Schroon Lake! Cozy Upstate Gem
3.0 star property
Schroon Lake
The price is NT$5,704
NT$6,882 total
includes taxes & fees
Sep 14 - Sep 15
Walk to Main St & Schroon Lake! Cozy Upstate Gem
Apartment (0 Bedroom) | Interior

14. Boat, Fish, Hike! Schroon Lake Getaway

Boat, Fish, Hike! Schroon Lake Getaway
3.0 star property
Schroon Lake
The price is NT$5,704
NT$6,882 total
includes taxes & fees
Sep 14 - Sep 15
Boat, Fish, Hike! Schroon Lake Getaway
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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Top Chestertown Hotel Reviews

Lakefront Terrace Resort

Lakefront Terrace Resort

8/10 Good
"The room was clean and the lake view was great. Stayed here before. Great location. It is quiet and away from the hustle and bustle."
Robert 2-night trip
Posted 3 hours ago
Lakefront Terrace Resort

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?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River 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.