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Check prices for these dates

Next weekend
Jun 27 - Jun 29
In two weeks
Jul 4 - Jul 6
In one month
Jul 18 - Jul 20
In two months
Aug 15 - Aug 17

Condo Rentals in Chestertown

Cozy retreat with fireplace, kayaks, and shared beach/pond access
Outdoor dining

Cozy retreat with fireplace, kayaks, and shared beach/pond access

9.0 out of 10, Wonderful, (17)
"We love the house super clean , the we love the area very peace and quiet , we love the private beach and the fresh air , definitely we be back again "
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Breathtaking Mountain Views Surround New Lakefront Condo
TV, fireplace

Breathtaking Mountain Views Surround New Lakefront Condo

9.8 out of 10, Exceptional, (90)
"Beautiful location will definitely be booking it next year. The staff was amazing."
Breathtaking Mountain Views Surround New Lakefront Condo
Serene getaway with fireplace, grill, kayaks & washer/dryer
Aerial view

Serene getaway with fireplace, grill, kayaks & washer/dryer

9.6 out of 10, Exceptional, (8)
"Comfortable beds, quiet great views of the lake; Pickleball and kayaks available."
Serene getaway with fireplace, grill, kayaks & washer/dryer
Peaceful Lakeside Retreat with Private Beach
Beach nearby, sun loungers, beach towels

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (17)
"The area was quiet and house was nice. Perfect for our needs."
Peaceful Lakeside Retreat with Private Beach
Charming 2-bedroom condo with fitness room, WiFi in Wonderful Lake George
A heated pool

Charming 2-bedroom condo with fitness room, WiFi in Wonderful Lake George

Charming 2-bedroom condo with fitness room, WiFi in Wonderful Lake George
Luxury Adirondack getaway with 4 private ensuites
Property grounds

Luxury Adirondack getaway with 4 private ensuites

Luxury Adirondack getaway with 4 private ensuites
Secluded gem with forest view, beach access & W/D
Aerial view

Secluded gem with forest view, beach access & W/D

8.0 out of 10, Very Good, (16)
"The property was excellent. The place had everything we needed to have a awesome thanksgiving. Clean and very comfortable.Close to all the stores. It snowed so we didn't get to go to the lakes but we sure enjoyed every moment here and we will visit again in the spring."
Secluded gem with forest view, beach access & W/D
Belmont Stakes Getaway – Stylish 2BR Suite Minutes from Saratoga!
Fridge, microwave, oven, stovetop

Belmont Stakes Getaway – Stylish 2BR Suite Minutes from Saratoga!

Belmont Stakes Getaway – Stylish 2BR Suite Minutes from Saratoga!
Tripp Lake retreat - monthly or seasonal rental only
Fridge, microwave, oven, stovetop

Tripp Lake retreat - monthly or seasonal rental only

Tripp Lake retreat - monthly or seasonal rental only
Lake View, Beautiful Condo, Private Beach and Pool

Lake View, Beautiful Condo, Private Beach and Pool

8.8 out of 10, Excellent, (10)
"Easy Peasy! Good communication. Clean and well stocked. Easy check in. Great location. Would gladly stay here again!"
Lake View, Beautiful Condo, Private Beach and Pool
Cozy Adirondack condo in quaint Chestertown, near Lake George & Gore Mountain
Fireplace

Cozy Adirondack condo in quaint Chestertown, near Lake George & Gore Mountain

$269 nightly
The price is $299
Jun 19 - Jun 20
Total includes taxes and fees
Cozy Adirondack condo in quaint Chestertown, near Lake George & Gore Mountain
Lakeside Condo on beautiful Lake George
Outdoor pool, a heated pool

Lakeside Condo on beautiful Lake George

Lakeside Condo on beautiful Lake George
MOTEL & COTTAGES
1 bedroom

MOTEL & COTTAGES

MOTEL & COTTAGES
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Why book your condo in Chestertown with Expedia?
Reserving a condo in Chestertown is as easy as deciding on your travel dates and picking an option that checks your boxes. In search of something affordable or luxurious, or a stay that also comes with a kitchen and laundry? Use Expedia’s search filters to narrow your results even further and find the perfect pad.
How can I find cheap condos in Chestertown?
With Expedia’s handy filter tool, locating cheap condos in Chestertown is easy. To find accommodations that are easy on your bank balance, narrow down your search by budget, amenities and star rating.
What is there to do in Chestertown near my condo?
If you’re eager to explore the best of Chestertown, find your way to Loon Lake Beach. It’s a hit with visitors and locals alike.