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Check prices for these dates

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18 Jul - 20 Jul
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25 Jul - 27 Jul
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8 Aug - 10 Aug
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5 Sep - 7 Sep

Villas in Chestertown

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

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

10.0 out of 10, Exceptional, (2)
"We had such a relaxing time here! Absolutely beautiful location and property. Lots of fun on the river and in the pool. Owners were fantastic and quick to respond. Very sweet arrival basket for us with all things Maryland! "
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, (19)
"My family stayed at The Beach Club for our yearly vacation. In 6th"
The price is SAR 9,376
SAR 13,062 total
includes taxes & fees
30 Jul - 31 Jul
Blake House Historic Estate with Private Inn
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
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, (14)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.
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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Frequently asked questions

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How can I find cheap villas in Chestertown?
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