Chestertown Vacation Homes

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Our top choices for Chestertown holiday homes

The Lily Pad at Loon Lake near Gore Mountain

Chestertown

Sophia H.

HK$4,619 total

includes taxes & fees

9 Jul - 10 Jul

Eagles Nest at Loon Lake near Gore Mountain

Chestertown

David S.

Adirondack Bungalow Getaway

Warrensburg

Evan S.

HK$1,523 total

includes taxes & fees

14 Jun - 15 Jun

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

Minerva

Christine T.

HK$2,125 total

includes taxes & fees

25 Jun - 26 Jun

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

North Creek

annie k.

HK$1,735 total

includes taxes & fees

15 Jun - 16 Jun

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

North Creek

Ryan H.

HK$2,083 total

includes taxes & fees

15 Jun - 16 Jun

10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home

Olmstedville

HK$6,623 total

includes taxes & fees

18 Jun - 19 Jun

Gorgeous Yurt in the Adirondacks for a Unique Glamping Getaway near Minerva, New York

Minerva

HK$2,073 total

includes taxes & fees

25 Jun - 26 Jun

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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent

"El lugar y su ubicación estan perfectas. El ambiente tranquilo y el personal atento."

Adirondack Retreat Inn & Suites

4/10 Poor

"We chose here for one reason, and one reason only... People claimed the beds were comfortable. Unfortunately, ours was terrible! After a very rough night for my wife with former back issues, I politely asked the desk for a remedy. I explained that we have grandchildren in the area and that if a solution could be found, they would have a regular customer returning every month. The nice lady at the desk said she would talk to the owner, but then called us a few minutes later to say there was nothing they could do. So we took it upon ourselves to go to walmart and buy their best 4 inch tempurpedic topper. This cost us $100 but gave us a great night sleep on the 2nd night. But here's the thing, we had already paid the hotel for that. If they had refunded our 2nd night, it would have paid for the topper. Better yet, if they had moved us or went out and bought the topper themselves, they would have had loyal customers that come every month even in the off-season. Two night stays, once a month, just $10 each night going towards that topper would have paid for itself in less than 3 months. Instead, they told us, "sorry, you will just have to suffer because you already paid us for the 2nd night"! Sad really...."

The Queensbury Hotel

10/10 Excellent

"We were in town for the Belmont races such a convenient location. Everything was amazing, from the beautiful entry to the nicely appointed room. Loved the convenience of breakfast downstairs and room service for the morning I didn’t feel like getting up early and the super cool bar. This was my first time in the lovely town of Glens Falls with its fun walkable downtown and top notch bars and restaurants we enjoyed every minute and will be back."

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