Chestertown Vacation Rentals from ￥22,152: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Chestertown?

Elizabeth. 15 minutes to Lake George.Seasonal Heated Pool. : This highly rated vacation home rental in Chestertown is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Our travelers also rate Eagles Nest at Loon Lake near Gore Mountain as a favorite home for rent in Chestertown.

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Our top choices for Chestertown vacation rentals

Private lakefront access just down the road with two docks, a cozy firepit, and comfortable outdoor seating. Perfect for fishing, enjoying the view, or unwinding by the water.

1. The Lily Pad at Loon Lake near Gore Mountain

Chestertown

Sara Beth E.

￥69,899 total

includes taxes & fees

Oct 5 - Oct 6

A log cabin interior with a stone fireplace, wooden ceiling beams, and a large leather sofa.

2. Authentic Log Cabin with Lake Views and Sauna

Chestertown

Joe F.

￥53,997 total

includes taxes & fees

Oct 4 - Oct 5

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

3. Trout House Village Resort

Hague

Matthew

￥22,152 total

includes taxes & fees

Oct 22 - Oct 23

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

4. Adirondack Mountains Cottage Near Gore Mountain!

Warrensburg

Pamela L.

￥63,782 total

includes taxes & fees

Oct 4 - Oct 5

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

5. Lincoln Log Colony

Lake George

David

￥23,770 total

includes taxes & fees

Oct 6 - Oct 7

A two-story building with a balcony and a flag.

6. Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6

North Creek

Michael

￥34,850 total

includes taxes & fees

Oct 5 - Oct 6

A spacious living area with a leather sofa, wooden ceiling, and large windows.

7. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

Warrensburg

Teresa B.

￥96,810 total

includes taxes & fees

Oct 5 - Oct 6

A cozy room with a bed, a sofa, and a balcony with chairs.

8. Secluded Adirondack Chalet/7 mins to Gore Mountain/ Fire pit/Fast Wi-Fi.

North Creek

Michael G.

￥38,604 total

includes taxes & fees

Oct 20 - Oct 21

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Top Chestertown Hotel Reviews

The Georgian Lakeside Resort

8/10 Good

"Fine establishment for families"

Adirondack Retreat Inn & Suites

10/10 Excellent

"We had a fantastic stay at Adirondack Retreat Inn & Suites and were really impressed with how much you get for the price. We rented one of their Deluxe Three Bedroom Houses, and at only $275 per night, it was an incredible value for a large family or group. The location is hard to beat. We were just a short walk from all the restaurants, shops and attractions along Canada Street, so once we arrived, we really didn’t need the car to enjoy downtown Lake George. Our house had three bedrooms, two bathrooms and plenty of room to spread out, with two queen beds and three double beds. The full kitchen was actually a FULL kitchen — pots, pans, dishes, silverware and everything you would need to cook a meal rather than just a microwave and mini fridge pretending to be a kitchen. Upstairs was probably our favorite part of the house. The bathroom had a beautiful Jacuzzi tub, and one of the bedrooms had its own private balcony with chairs and a small table. It was the perfect spot to sit outside and take in the incredible views of the mountains surrounding Lake George. The amenities around the property were another pleasant surprise. The enclosed heated pool is open year-round, stays open until 10 p.m. and was a perfect 86 degrees during our stay. There’s also a beautiful fire pit surrounded by Adirondack chairs, and they even provide bundles of firewood for guests at no charge — such a nice touch."

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."

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

10/10 Excellent

"The property is immense! We ended up being 7 adults and 6 children and there was no problem with sleeping/playing space. The pool is immaculately maintained. Although there were a couple of bumps in the road, the owner and staff were quick to remedy. I particularly enjoyed the screened in porch! A true pleasure for a gal not into dealing with the negative parts of nature, i.e. bugs, bees, etc.! I would heartily recommend this property for fun loving families...with a shout out to The Remington Restaurant who accomodated our large family with wonderful food and drink!"

Find out more about Chestertown

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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.

What are some of the best vacation home rentals in Chestertown?

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.: This highly rated vacation home rental in Chestertown is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Our travelers also rate Eagles Nest at Loon Lake near Gore Mountain as a favorite home for rent in Chestertown.

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.

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Check prices for these dates

Our top choices for Chestertown vacation rentals

1. The Lily Pad at Loon Lake near Gore Mountain

2. Authentic Log Cabin with Lake Views and Sauna

3. Trout House Village Resort

4. Adirondack Mountains Cottage Near Gore Mountain!

5. Lincoln Log Colony

6. Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6

7. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

8. Secluded Adirondack Chalet/7 mins to Gore Mountain/ Fire pit/Fast Wi-Fi.

9. Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6

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

11. Lovely 3-bedroom house close to Gore Mountain for skiing.

12. Gore Mountain Lift View: North Creek Main St Apt 2

13. Camp RiverWood on the Hudson River

14. Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8

15. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

16. Beautiful cottage on quiet country road walking distance to charming North Creek

17. The Office at North Creek All Season Rental

18. The Elms Waterfront Cottages

19. Gorgeous Mountain Top Cabin with Beautiful Views

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

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

The Georgian Lakeside Resort

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

Great Escape Lodge & Indoor Waterpark

Adirondack Retreat Inn & Suites

Super 8 by Wyndham Lake George/Downtown

Baymont by Wyndham Queensbury / Lake George

Nordick's Inn

Pine Tree Motel & Cabins

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Find out more about Chestertown

Frequently asked questions

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