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$3,565 total

includes taxes & fees

9 Jun - 10 Jun

Eagles Nest at Loon Lake near Gore Mountain

Chestertown

David S.

HK$5,470 total

includes taxes & fees

10 Jun - 11 Jun

Adirondack Bungalow Getaway

Warrensburg

Evan S.

HK$1,600 total

includes taxes & fees

7 Jul - 8 Jul

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

Minerva

Christine T.

HK$2,125 total

includes taxes & fees

9 Jun - 10 Jun

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

North Creek

annie k.

HK$1,734 total

includes taxes & fees

10 Jun - 11 Jun

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

North Creek

Ryan H.

HK$1,908 total

includes taxes & fees

9 Jun - 10 Jun

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

Olmstedville

HK$6,621 total

includes taxes & fees

10 Jun - 11 Jun

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

Minerva

HK$2,046 total

includes taxes & fees

9 Jun - 10 Jun

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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Lake George

8/10 Good

"great location and great pool, nice free breakfast"

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

8/10 Good

"We stayed for the Belmont and the price was great for reserving 2 rooms. When we arrived, Nikita at the front desk said she insured we got 2 of the few rooms that adjoin. She also gave us bottled water and a bag of snacks. All good was the fridge with freezer, bathroom toiletries, shower and bed. Alas, in room coffee is usually a mediocre affair at this price point but they do supply free coffee in the lobby all day/evening with flavored creamers. The free breakfast choices were plenty. It was pretty quiet but we had rooms next to the pool which was closed due to weather so it is probably noisier when open. Overall we agreed we would definitely stay again."

The Georgian Lakeside Resort

8/10 Good

"My stay here was lovely. The staff was very friendly and helpful and the room was clean and spacious. The location is amazing - a minute walk to the busy lake George area (although I had no issue with noise at night). The only thing missing was complementary lotion to go with the bathroom stuff (they provided shampoo, conditioner, and body wash). Also, the room had minimal lighting which isn’t terrible but it was a it dark for my taste. Otherwise a great stay!"

Lodge at Schroon Lake

10/10 Excellent

"The place in general has amazing amenities, including a basketball court, mini golf, a game room, outdoor fire pits, live music, an indoor pool, etc. The downside of our recent day was that the beach area was not yet open for the season, even though it was already early June. So we were unable to rent kayaks and use the lake. Also, only one restaurant was open because the tavern was fully booked out by a wedding."

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