Chestertown Vacation Rentals from $168: 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?

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.

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.

Check prices for these dates

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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.

$406 nightly

Oct 5 - Oct 6

Total with taxes and fees

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.

$309 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

3. Adirondack Mountains Cottage Near Gore Mountain!

Warrensburg

Pamela L.

$365 nightly

Oct 4 - Oct 5

Total with taxes and fees

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.

$178 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

$203 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

6. Trout House Village Resort

Hague

Matthew

$153 nightly

Oct 20 - Oct 21

Total with taxes and fees

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.

$219 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

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

Schroon Lake

Kenneth

$155 nightly

Oct 5 - Oct 6

Total with taxes and fees

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Top Chestertown Hotel Reviews

Great Escape Lodge & Indoor Waterpark

10/10 Excellent

"Had a great trip can't wait to come back"

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

Everything you need to know about Chestertown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chestertown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chestertown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $168 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Things to do in Lake George

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.

Room 1

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

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

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