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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Villas in Chestertown

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Indoor pool

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

10.0 out of 10, Exceptional, (10)
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Blake House Historic Estate with Private Inn
Pool

Blake House Historic Estate with Private Inn

10.0 out of 10, Exceptional, (21)
"My family stayed at The Beach Club for our yearly vacation. In 6th"
Blake House Historic Estate with Private Inn
Stunning waterfront villa with indoor pool and kids swing set and play area.
Spa

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (17)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.
Cozy Waterfront 3-bedroom villa with fitness/theater/game room, WiFi in Dundalk
Smart TV, fireplace, foosball

Cozy Waterfront 3-bedroom villa with fitness/theater/game room, WiFi in Dundalk

10.0 out of 10, Exceptional, (2)
"The property is clean, newly updated and spacious with an open concept floor plan. The A/C is more than adequate. The property is located on a picturesque inlet off of the bay with plenty of backyard space, a hot tub, decks with outdoor furniture and a game room downstairs."
Cozy Waterfront 3-bedroom villa with fitness/theater/game room, WiFi in Dundalk
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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Top Chestertown Hotel Reviews

Frequently asked questions

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