Chestertown Vacation Rentals from $151: 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 61 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

A wooden table with a bottle and glasses of beer, set against a backdrop of a house with a balcony and a mountain view.

1. Lily Pad South at Loon Lake near Gore Mountain

Chestertown

louis

$239 nightly

Sep 20 - Sep 21

Total with taxes and fees

2. The Lily Pad at Loon Lake near Gore Mountain

Chestertown

Sophia H.

$449 nightly

Sep 20 - Sep 21

Total with taxes and fees

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

3. Authentic Log Cabin with Lake Views and Sauna

Chestertown

Joe F.

$307 nightly

Aug 23 - Aug 24

Total with taxes and fees

A two-story wooden house with a balcony, a front porch, and a staircase leading to the upper level.

4. Eagles Nest at Loon Lake near Gore Mountain

Chestertown

David S.

$680 nightly

Sep 13 - Sep 14

Total with taxes and fees

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

5. Adirondack Mountains Cottage Near Gore Mountain!

Warrensburg

Roy M.

$367 nightly

Aug 25 - Aug 26

Total with taxes and fees

A wooden cabin with a porch and a deck, surrounded by trees.

6. Lake George Escape - Campground

Diamond Point

Brittany

$164 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

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

Schroon Lake

Kevin

$150 nightly

Aug 23 - Aug 24

Total with taxes and fees

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

8. Trout House Village Resort

Hague

Matthew

$172 nightly

Sep 14 - Sep 15

Total with taxes and fees

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Top Chestertown Hotel Reviews

Tiki Resort

8/10 Good

"Room was well kept and spacious. Outside of property could use some attention. Laurie in the bar was awesome. We would stay again"

Lodge at Schroon Lake

8/10 Good

"Great amenities and a super fun game room. Some of the common hallways with carpeting in the main lodge definitely had a pet smell to them and I am not sensitive to smells. The room itself was very clean and well-maintained. Food at the Brown Swan was amazing. One warning - if you rent boats be sure to get a receipt! I was charged more than I’d expected after charging boat rentals to the room and haven’t been able to get to the bottom of it yet."

The Georgian Lakeside Resort

10/10 Excellent

"We had a wonderful stay at the hotel and truly enjoyed every part of it! The location was absolutely perfect, and the views were beautiful. We especially loved the pool — it was a great place to relax and enjoy our time. The food was also delicious, and everything was well prepared. Overall, the hotel had a great atmosphere, beautiful surroundings, and everything we needed for a relaxing getaway. We really enjoyed our stay and would definitely recommend this hotel to others. We would love to come back again! ❤️"

Lakefront Terrace Resort

10/10 Excellent

"Absolutely Amazing Stay! ⭐⭐⭐⭐⭐ We had such a wonderful stay at this motel! The place is absolutely beautiful, peaceful, and very clean. The view was breathtaking and honestly one of the best parts of our stay — we could have sat there for hours just enjoying the scenery! 😍 The swimming pool was also extremely clean and well maintained, which made it even more enjoyable, especially for the kids. Everything was neat, comfortable, and welcoming. The whole property has such a relaxing atmosphere, and you can really tell that they care about keeping the place nice for their guests. We had a fantastic experience and would definitely recommend this motel to anyone looking for a beautiful, clean, and relaxing place to stay. We would absolutely come back again! ❤️"

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 $151 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 61 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.

Chestertown Vacation Rentals

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Check prices for these dates

Our top choices for Chestertown vacation rentals

1. Lily Pad South at Loon Lake near Gore Mountain

2. The Lily Pad at Loon Lake near Gore Mountain

3. Authentic Log Cabin with Lake Views and Sauna

4. Eagles Nest at Loon Lake near Gore Mountain

5. Adirondack Mountains Cottage Near Gore Mountain!

6. Lake George Escape - Campground

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

8. Trout House Village Resort

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

10. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

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

12. Camp RiverWood on the Hudson River

13. Adirondack Bungalow Getaway

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

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

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

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

18. The Office at North Creek All Season Rental

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

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

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

Tiki Resort

Find out more about Chestertown

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