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Search Condo Rentals in Chestertown

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Compare 16 Condo Rentals in Chestertown with updated reviews, rates, and availability.

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

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

9.0 out of 10, Wonderful, (16)
"Beautiful place wood location"
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Peaceful Lakeside Retreat with Private Beach
Lake

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (17)
"It was clean, nicely decorated, everything was new and in working order. Would suggest adding some face/wash cloths and top sheet for bed. Also, bed was comfortable but squeaked every time you made a move. All in all nice property and enjoyed our time :)"
Peaceful Lakeside Retreat with Private Beach
Serene getaway with fireplace, grill, kayaks & washer/dryer

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

9.8 out of 10, Exceptional, (7)
"A lovely get away"
Serene getaway with fireplace, grill, kayaks & washer/dryer
Condo with private community beach/pond access - on-site tennis & golf nearby

Condo with private community beach/pond access - on-site tennis & golf nearby

9.2 out of 10, Wonderful, (7)
"The stay was great! The property had all basic necessities to last our time there. There was a bit of confusion about trash disposal but the neighbors were kind. Our WiFi service was a bit spotty but otherwise no other complaints. Would recoommend!"
Condo with private community beach/pond access - on-site tennis & golf nearby
Discover fall in the Adirondacks
Miscellaneous

Discover fall in the Adirondacks

9.8 out of 10, Exceptional, (12)
"Great responsiveness... clean unit... Great Location!"
Discover fall in the Adirondacks
Secluded gem with forest view, beach access & W/D

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

7.8 out of 10, Good, (15)
"Overall the online listing is a very accurate representation of the property. It has a very rustic cabin feel. The pond that you can visit is wonderful and well staffed and taken care of. My only complaint is there was no air conditioning in the apartment and it got very hot."
Secluded gem with forest view, beach access & W/D
Luxury Adirondack getaway with 4 private ensuites
Living area

Luxury Adirondack getaway with 4 private ensuites

Luxury Adirondack getaway with 4 private ensuites
Beautiful waterfront 2-bedroom 2-bathroom condo with pool and beach access
Marina

Beautiful waterfront 2-bedroom 2-bathroom condo with pool and beach access

9.4 out of 10, Exceptional, (3)
"Our Family of 5 travels to Lake George every summer for a week of fun on the water and relaxing time with extended family. This property is centrally located to Great Restaurants and activities in Diamond Point and Village of Lake George. Only a 15minute drive to the most popular hiking trails. This property is not only a summer getaway but would be a great place to stay in the Winter to Ski Gore Mountain. It has a beautiful wood burning fireplace in the family room. "
Beautiful waterfront 2-bedroom 2-bathroom condo with pool and beach access
Breathtaking Mountain Views Surround New Lakefront Condo
Livingroom with natural stone fireplace and panoramic views of the lake!

Breathtaking Mountain Views Surround New Lakefront Condo

9.8 out of 10, Exceptional, (90)
"My family and I stayed here for 5 nights and it was a comfy, cozy and good experience. Home is kept up very nicely, rooms are large and clean."
Breathtaking Mountain Views Surround New Lakefront Condo
Lake View, Beautiful Condo, Private Beach and Pool
Boat Dock

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 Pond Retreat, Unit E | Condo in Warrensburg

Tripp Pond Retreat, Unit E | Condo in Warrensburg

10.0 out of 10, Exceptional, (1)
"Perfect for us - we traveled with 2 grandchildren, 8 and 12. The condo was very clean, has a well equipped kitchen, and the tennis courts, pickle ball courts and basketball court were right outside the door. The grill in the outdoor porch worked well. Beach, with chairs, umbrellas and boats was a 3 minute walk down from the condo. Would definitely return!"
Tripp Pond Retreat, Unit E | Condo in Warrensburg
Tripp Lake retreat - monthly or seasonal rental only
Interior

Tripp Lake retreat - monthly or seasonal rental only

Tripp Lake retreat - monthly or seasonal rental only
Magnificent Glens Falls Retreat
Master Bedroom w/ large ensuite bathroom

Magnificent Glens Falls Retreat

Magnificent Glens Falls Retreat
Lakeside Condo on beautiful Lake George
Property grounds

Lakeside Condo on beautiful Lake George

Lakeside Condo on beautiful Lake George
MOTEL & COTTAGES
Room

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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Other property types in Chestertown

Peaceful Lakeside Retreat with Private Beach
Lake

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (17)
"It was clean, nicely decorated, everything was new and in working order. Would suggest adding some face/wash cloths and top sheet for bed. Also, bed was comfortable but squeaked every time you made a move. All in all nice property and enjoyed our time :)"
Peaceful Lakeside Retreat with Private Beach
Cozy retreat with fireplace, kayaks, and shared beach/pond access

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

9.0 out of 10, Wonderful, (16)
"Beautiful place wood location"
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Great Room

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (53)
"Host John was like best of friends. Couldn’t have done more for us. Sue too was very nice. Pearl and ruby, their do"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
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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