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

Our top choices for Chestertown holiday rentals

A wooden deck with a grill, two red chairs, and a welcome sign.

1. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
3.0 star property
Warrensburg
The price is RM837
RM1,620 total
includes taxes & fees
25 Sept - 26 Sept
Adirondack Mountains Cottage Near Gore Mountain!
A lakeside cabin with a wooden deck and a view of the lake.

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 RM541
RM702 total
includes taxes & fees
30 Sept - 1 Oct
Trout House Village Resort
A wooden cabin with a porch and a deck, surrounded by trees.

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 RM668
RM741 total
includes taxes & fees
21 Sept - 22 Sept
Lake George Escape - Campground
A poolside area with a wooden deck, a grill, and a flower planter.

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 RM474
RM526 total
includes taxes & fees
30 Sept - 1 Oct
Lincoln Log Colony
A lakeside dock with boats and a picnic table.

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 RM1,280
RM1,421 total
includes taxes & fees
12 Oct - 13 Oct
The Elms Waterfront Cottages
A landscaped garden with a fountain, flags, and a view of a body of water.

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 RM562
RM691 total
includes taxes & fees
13 Sept - 14 Sept
Walk to Schroon Lake! Studio w/ Shared Fire Pit
A sandy beach with a calm lake, trees, and a distant hill.

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 RM561
RM690 total
includes taxes & fees
13 Sept - 14 Sept
Schroon Lake Room < 1 Mi to Marina & Beach!
A beach with a stone wall, trees, and a calm lake.

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 RM562
RM691 total
includes taxes & fees
14 Sept - 15 Sept
Cozy Room Near Schroon Lake Marina, Town & Beach!
A beach with a stone wall, trees, and a clear sky.

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 RM562
RM691 total
includes taxes & fees
14 Sept - 15 Sept
Close to Marina, Beach & Town! Schroon Lake Escape
A beach with a stone wall, trees, and a calm lake.

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 RM562
RM691 total
includes taxes & fees
24 Sept - 25 Sept
Easy Schroon Lake Living! Close to Marina & Town
A sandy beach with a stone wall, trees, and a clear sky.

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 RM562
RM691 total
includes taxes & fees
14 Sept - 15 Sept
Boat, Fish & Hike! All-season Schroon Lake Getaway
A lakeside view with a wooden deck leading to a sandy beach.

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 RM737
RM889 total
includes taxes & fees
24 Sept - 25 Sept
< 1 Mi to Boat Launch! Schroon Lake Basecamp
A stone building with a balcony overlooking a lake, a grassy lawn, and a tree.

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 RM737
RM889 total
includes taxes & fees
24 Sept - 25 Sept
Walk to Main St & Schroon Lake! Cozy Upstate Gem
A lakeside view with a wooden deck leading to a sandy beach.

14. Boat, Fish, Hike! Schroon Lake Getaway

Boat, Fish, Hike! Schroon Lake Getaway
3.0 star property
Schroon Lake
The price is RM737
RM889 total
includes taxes & fees
24 Sept - 25 Sept
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

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

10/10 Excellent
"Clean room, good breakfast , very friendly staff"
vismand 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Find out more about Chestertown

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

  • View our selection of featured holiday rentals in Chestertown
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  • Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

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

Frequently asked questions

Can I find holiday rentals in Chestertown?

Yes, there are holiday rentals close to the most popular sights in Chestertown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffee shops and forests during your trip.

How many holiday rentals will I find in Chestertown?

With 63 Expedia holiday rentals, you're guaranteed 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 holiday rental in Chestertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chestertown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.