Chestertown Vacation Rentals from $115: Search Short-Term Rentals

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

Adirondack Bungalow Getaway : Located near Chestertown, this vacation home rental is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind.

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In two weeks

In two months

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In four months

Our top choices for Chestertown vacation rentals

Lily Pad South at Loon Lake near Gore Mountain

Chestertown

louis

$213 nightly

Jun 8 - Jun 9

Total with taxes and fees

Lily Pad North at Loon Lake near Gore Mountain

Chestertown

T

The Lily Pad at Loon Lake near Gore Mountain

Chestertown

Sophia H.

$414 nightly

Jun 9 - Jun 10

Total with taxes and fees

Eagles Nest at Loon Lake near Gore Mountain

Chestertown

David S.

$632 nightly

Jun 10 - Jun 11

Total with taxes and fees

Authentic Log Cabin with Lake Views and Sauna

Chestertown

Joe F.

$380 nightly

Jul 5 - Jul 6

Total with taxes and fees

Tent in Indian Lake+Pet Friendly+Lake Front

Indian Lake

$100 nightly

Jun 12 - Jun 13

Total with taxes and fees

Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.

Hadley

Kerrie F.

$195 nightly

Jun 8 - Jun 9

Total with taxes and fees

Cabin, 1 Bedroom, Non Smoking, Lake View | Egyptian cotton sheets, premium bedding, individually decorated

Trout House Village Resort

Hague

Matthew

$189 nightly

Jun 5 - Jun 6

Total with taxes and fees

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Top Chestertown Hotel Reviews

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

10/10 Excellent

"j ai aimé mon sejour"

The Georgian Lakeside Resort

6/10 Okay

"The room was fine - basic and what you’d expect for $99/night. When we were told at check in that we were “upgraded”, I expected more than a view of the parking lot and a barebones room where the AC is manually operated and cuts out every 5 minutes. It certainly was a more motel feel than hotel or resort. The walls are very thin and if you have trouble with stairs, be sure to request a ground level floor. The restaurant is through the galley, in case you are wondering, as I spent 3 days looking for it despite the map. The staff was fine however the “breakfast” included doesn’t include coffee! When I mentioned it at check out, the staff’s response was “well we don’t really have control over the restaurant…”"

Six Flags Great Escape Lodge & Indoor Waterpark

2/10 Terrible

"The first of my two night stay was great - the second was horrible. We were placed in the middle of two different high school graduation celebrations - we have a 2 and 4 year old - no one in my family got any sleep- tried to contact management and received no response"

Depe Dene Lakeside Resort

8/10 Good

"We only stayed one night, but looked like a great property. Stunning views of the lake and mountains. We hung out on the small beach for a while and the patio next to it. The issue was the smell of pot everywhere. It was lingering around the beach and the worse was our neighbor smoking out front right next to our door (small table and chairs are setup next to front doors) and the smell crept into our room. There was a playground (also smelled) and heated outdoor pool (which we did not make it to). We visited the restaurant next door (walking distance) and had a delicious breakfast."

The Queensbury Hotel

10/10 Excellent

"It’s an old treasure. It could use some dark shades but otherwise its a great comfortable bed in a retro setting offering a touch of the past. We felt fortunate to get it at an unusually low price(off season) Ive been in similar hotels that had more of everything but the price point of those were $500 + . We kept extending our stay due to a family need and had no problem doing so. Martinis in the bar were very good"

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 $115 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?

Adirondack Bungalow Getaway: Located near Chestertown, this vacation home rental is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind.

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?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Hudson River and Loon Lake 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

Lily Pad South at Loon Lake near Gore Mountain

Lily Pad North at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Authentic Log Cabin with Lake Views and Sauna

Tent in Indian Lake+Pet Friendly+Lake Front

Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.

Trout House Village Resort

Boat, Fish, Hike! Schroon Lake Getaway

RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS

ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access

PET FRIENDLY Adirondacks Log Cabin! Lake George, Saratoga, SPAC, Sacandaga

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

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

GLAMP SUZANNE: CANVAS CABIN ON PRETTY ADIRONDACK FARM OFFERS PRIVACY AND VIEWS

Camp Lillian Gorgeous New Cabin with Mountain Views

Handcrafted mountain cabin with gorgeous views

< 1 Mi to Boat Launch! Schroon Lake Basecamp

Beautiful cottage on scenic Adirondack hobby farm

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

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

The Georgian Lakeside Resort

Six Flags Great Escape Lodge & Indoor Waterpark

Depe Dene Lakeside Resort

The Queensbury Hotel

Lodge at Schroon Lake

Scotty's Lakeside Resort

Courtyard by Marriott Lake George

La Quinta Inn & Suites by Wyndham Lake George

Find out more about Chestertown

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