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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chestertown holiday rentals

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

1. Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.6 out of 10, Exceptional, (28 reviews)
"It was a great place, clean rooms, nice environment, cabins, family friendly, right on lake"
United States
Matthew
The price is Rp1.866.652
Rp2.519.459 total
includes taxes & fees
20 Oct - 21 Oct
Trout House Village Resort
A poolside area with a wooden deck, a grill, and a flower planter.

2. Lincoln Log Colony

Lincoln Log Colony
2.0 star property
Lake George
8.8 out of 10, Excellent, (25 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 Rp2.435.696
Rp2.703.623 total
includes taxes & fees
15 Oct - 16 Oct
Lincoln Log Colony
A sandy beach with a calm lake, trees, and a distant hill.

3. 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 Rp2.470.062
Rp3.038.534 total
includes taxes & fees
12 Oct - 13 Oct
Schroon Lake Room < 1 Mi to Marina & Beach!
A lakeside dock with boats and a picnic table.

4. 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 Rp5.638.185
Rp6.258.385 total
includes taxes & fees
11 Oct - 12 Oct
The Elms Waterfront Cottages
A beach with a stone wall, trees, and a calm lake.

5. 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 Rp2.470.062
Rp3.038.534 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Room Near Schroon Lake Marina, Town & Beach!
A stone building with a balcony overlooking a lake, a grassy lawn, and a tree.

6. 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 Rp3.239.719
Rp3.908.247 total
includes taxes & fees
12 Oct - 13 Oct
Walk to Main St & Schroon Lake! Cozy Upstate Gem
A beach with a stone wall, trees, and a clear sky.

7. 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 Rp2.470.062
Rp3.038.534 total
includes taxes & fees
12 Oct - 13 Oct
Close to Marina, Beach & Town! Schroon Lake Escape
A beach with a stone wall, trees, and a calm lake.

8. 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 Rp2.470.062
Rp3.038.534 total
includes taxes & fees
12 Oct - 13 Oct
Easy Schroon Lake Living! Close to Marina & Town
A sandy beach with a stone wall, trees, and a clear sky.

9. 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 Rp2.470.062
Rp3.038.534 total
includes taxes & fees
12 Oct - 13 Oct
Boat, Fish & Hike! All-season Schroon Lake Getaway
A lakeside view with a wooden deck leading to a sandy beach.

10. < 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 Rp3.239.719
Rp3.908.247 total
includes taxes & fees
12 Oct - 13 Oct
< 1 Mi to Boat Launch! Schroon Lake Basecamp
A landscaped garden with a fountain, flags, and a view of a body of water.

11. 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 Rp2.470.062
Rp3.038.534 total
includes taxes & fees
11 Oct - 12 Oct
Walk to Schroon Lake! Studio w/ Shared Fire Pit
A lakeside view with a wooden deck leading to a sandy beach.

12. Boat, Fish, Hike! Schroon Lake Getaway

Boat, Fish, Hike! Schroon Lake Getaway
3.0 star property
Schroon Lake
The price is Rp3.239.719
Rp3.908.247 total
includes taxes & fees
12 Oct - 13 Oct
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

Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

8/10 Good
"Breakfast wasn’t very good"
Robert 1-night trip
Posted 18 hours ago
Baymont by Wyndham Queensbury / Lake George

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia.co.id! 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 62 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?

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 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.