Photo by Julie Miller

Search Condos in Chestertown

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Condo Rentals in Chestertown

Peaceful Lakeside Retreat with Private Beach
Beach nearby, sun-loungers, beach towels

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (20)
"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

10.0 out of 10, Exceptional, (1)
"We had a wonderful two night stay. Enjoyed the Lake and attractions!"
Charming 2-bedroom condo with fitness room, WiFi in Wonderful Lake George
Serene getaway with fireplace, grill, kayaks & washer/dryer
Outdoor dining

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

9.6 out of 10, Exceptional, (9)
"Comfortable beds, quiet great views of the lake; Pickleball and kayaks available."
Serene getaway with fireplace, grill, kayaks & washer/dryer
Breathtaking Mountain Views Surround New Lakefront Condo
TV, fireplace

Breathtaking Mountain Views Surround New Lakefront Condo

9.8 out of 10, Exceptional, (91)
"Beautiful location will definitely be booking it next year. The staff was amazing."
Breathtaking Mountain Views Surround New Lakefront Condo
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Exterior

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

8.6 out of 10, Excellent, (20)
"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
Luxury Adirondack getaway with 4 private ensuites
Property grounds

Luxury Adirondack getaway with 4 private ensuites

Luxury Adirondack getaway with 4 private ensuites
Upscale Downtown Glens Falls Suite — Walk to Museums, Shops & Dining
Fridge, microwave, oven, stovetop

Upscale Downtown Glens Falls Suite — Walk to Museums, Shops & Dining

8.0 out of 10, Very good, (1)
"Beautifully decorated and lots of edible goodies! The robes were a nice touch. Couple of issues arose which were quickly addressed. We would definitely return. "
Upscale Downtown Glens Falls Suite — Walk to Museums, Shops & Dining
Lake View, Beautiful Condo, Private Beach and Pool
Marina

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
Tripp Lake retreat - monthly or seasonal rental only
Dining

Tripp Lake retreat - monthly or seasonal rental only

Tripp Lake retreat - monthly or seasonal rental only
Secluded gem with forest view, beach access & W/D
Exterior

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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Heritage of Lake George

Heritage of Lake George

10/10 Excellent
"close to town and all that goes with iy"
david 3-night trip
Posted 21 hours ago
Heritage of Lake George

Frequently asked questions

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.