Chestertown Vacation Rentals from ￥20,363: Search Short-Term Rentals

Q: 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.

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.

Q: 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.

Q: 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.

Q: 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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Our top choices for Chestertown vacation rentals

1. The Lily Pad at Loon Lake near Gore Mountain

Chestertown

Sara Beth E.

￥65,992 total

includes taxes & fees

Sep 28 - Sep 29

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.

￥50,978 total

includes taxes & fees

Sep 28 - Sep 29

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

3. Adirondack Mountains Cottage Near Gore Mountain!

Warrensburg

Jennie M.

￥60,755 total

includes taxes & fees

Oct 4 - Oct 5

A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, a dishwasher, and a coffee maker.

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

Warrensburg

Matthew L.

￥28,909 total

includes taxes & fees

Sep 29 - Sep 30

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

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

North Creek

Michael

￥33,944 total

includes taxes & fees

Sep 28 - Sep 29

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

6. Trout House Village Resort

Hague

Matthew

￥22,139 total

includes taxes & fees

Oct 20 - Oct 21

A covered porch with a table and chairs, overlooking a residential area with houses and a street.

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

North Creek

Lynda N.

￥35,864 total

includes taxes & fees

Sep 28 - Sep 29

A sandy beach with a calm lake, trees, and a distant hill.

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

Schroon Lake

Kenneth

￥27,548 total

includes taxes & fees

Sep 28 - Sep 29

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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent

"Great location. Super friendly staff. Very clean hotel. Spacious rooms. Breakfast was good. Have stayed there before and will definitely be back."

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."

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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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?

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 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. Adirondack Mountains Cottage Near Gore Mountain!

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

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

6. Trout House Village Resort

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

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

9. Adirondack Bungalow Getaway

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

11. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

12. GLAMP RICHARD ON ADIRONDACK FLOWER FARM

13. Glamp Thomas On Adk Farm Offers Privacy, Stargazing And Mountain Views

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

15. Boat, Fish & Hike! All-Season Schroon Lake Getaway

16. Camp RiverWood on the Hudson River

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

18. Little Black Aframe by the Brook- 5m to Waterfall

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

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

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Lake George

Surfside On The Lake

Adirondack Retreat Inn & Suites

Nordick's Inn

Depe Dene Lakeside Resort

Lakefront Terrace Resort

Courtyard by Marriott Lake George

Pine Tree Motel & Cabins

The Georgian Lakeside Resort

Find out more about Chestertown

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