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

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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

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 ₹19,592
₹37,891 total
includes taxes & fees
17 Sept - 18 Sept
Adirondack Mountains Cottage Near Gore Mountain!
Cabin, 1 Bedroom, Non Smoking, Lake View | Egyptian cotton sheets, premium bedding, iron/ironing board, free WiFi

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 ₹12,649
₹16,418 total
includes taxes & fees
13 Sept - 14 Sept
Trout House Village Resort
WiFi

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 ₹15,603
₹17,318 total
includes taxes & fees
21 Sept - 22 Sept
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 ₹11,093
₹12,314 total
includes taxes & fees
15 Sept - 16 Sept
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 ₹29,870
₹33,156 total
includes taxes & fees
23 Sept - 24 Sept
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 ₹13,086
₹16,097 total
includes taxes & fees
14 Sept - 15 Sept
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 ₹13,086
₹16,097 total
includes taxes & fees
23 Sept - 24 Sept
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 ₹13,086
₹16,097 total
includes taxes & fees
23 Sept - 24 Sept
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 ₹13,086
₹16,097 total
includes taxes & fees
23 Sept - 24 Sept
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 ₹13,086
₹16,097 total
includes taxes & fees
23 Sept - 24 Sept
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 ₹13,086
₹16,097 total
includes taxes & fees
23 Sept - 24 Sept
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 ₹17,163
₹20,705 total
includes taxes & fees
23 Sept - 24 Sept
< 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 ₹17,163
₹20,705 total
includes taxes & fees
23 Sept - 24 Sept
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 ₹17,163
₹20,705 total
includes taxes & fees
23 Sept - 24 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

8/10 Good
"Great place to stop on my way to Canada. Staaf at front desk was very inviting. Place was quiet and safe for a single traveler. Rooms are older but well kept. Breakfast was good just missing some fresh fruit. Price was very affordable."
Jennifer 1-night trip
Posted 4 hours ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Find out more about Chestertown

Holiday Rentals in 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
  • Use the map to find apartments and other holiday homes in the Chestertown neighbourhood you prefer
  • 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.