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?

Eagles Nest at Loon Lake near Gore Mountain : This highly rated vacation home rental in Chestertown is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 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.

Q: How many vacation rentals will I find in Chestertown?

With 59 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chestertown vacation rentals

1. Authentic Log Cabin with Lake Views and Sauna

Chestertown

Joe F.

$309 nightly

Aug 19 - Aug 20

Total with taxes and fees

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

Schroon Lake

Kevin

$150 nightly

Aug 5 - Aug 6

Total with taxes and fees

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

North Creek

annie k.

$227 nightly

Aug 5 - Aug 6

Total with taxes and fees

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

North Creek

Michael

$219 nightly

Aug 5 - Aug 6

Total with taxes and fees

5. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

Warrensburg

Teresa B.

$562 nightly

Aug 5 - Aug 6

Total with taxes and fees

6. The Office at North Creek All Season Rental

North Creek

Brandon A.

$235 nightly

Aug 5 - Aug 6

Total with taxes and fees

7. Camp RiverWood on the Hudson River

North Creek

Paul N.

$225 nightly

Aug 5 - Aug 6

Total with taxes and fees

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

North Creek

Lynda N.

$237 nightly

Aug 5 - Aug 6

Total with taxes and fees

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Top Chestertown Hotel Reviews

Adirondack Retreat Inn & Suites

10/10 Excellent

"Loved our stay at this hotel. Great location to main strip, walking distance to restaurants, shops and Shepard park. Indoor pool was a great amenity as we had some rain. Had a minor issue with our AC on the second night and notified the staff in the office first thing the next morning. The owner was at our room 10 minutes later fixing the issue in no time. Great customer service and will definitely stay here again our next time in Lake George!"

Baymont by Wyndham Queensbury / Lake George

8/10 Good

"Our rooms were clean and the beds were comfortable, mattresses were definitely fairly new. The furniture was dated but when just basically sleeping in the rooms with only being in them from basically 8pm-8am that doesn’t really matter. The mini fridge worked well and kept waters good and cold."

The Georgian Lakeside Resort

10/10 Excellent

"We went to dinner on Friday and lunch on Saturday and they were out of a lot of things on the menu. Ex: chicken wings, clams. Parking is a problem, not sure if they have enough spots for each room. The staff at the desk and restaurant were not the friendliest and service was slow at the restaurant. Pool section and beach was very nice."

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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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?

Eagles Nest at Loon Lake near Gore Mountain: This highly rated vacation home rental in Chestertown is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 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.

How many vacation rentals will I find in Chestertown?

With 59 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.

Room 1

Check prices for these dates

Our top choices for Chestertown vacation rentals

1. Authentic Log Cabin with Lake Views and Sauna

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

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

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

5. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

6. The Office at North Creek All Season Rental

7. Camp RiverWood on the Hudson River

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

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

10. Lake George Escape - Campground

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

12. Walk to Schroon Lake! Studio w/ Shared Fire Pit

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

14. Adirondack Bungalow Getaway

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

16. Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied

17. Little Red Cabin by the Brook- 5m to Waterfall

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

19. ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

20. Lincoln Log Colony

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

Adirondack Retreat Inn & Suites

Baymont by Wyndham Queensbury / Lake George

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

Six Flags Great Escape Lodge & Indoor Waterpark

Tiki Resort

The Georgian Lakeside Resort

Holiday Inn Resort Lake George - Adirondack Area by IHG

Peaceful Lakeside Retreat with Private Beach

Find out more about Chestertown

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