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Search Villas in Chestertown

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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 4 Villas in Chestertown with updated reviews, rates, and availability.

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

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

9.8 out of 10, Exceptional, (13)
"The house was beautiful. We enjoyed the pool. The kitchen was wonderful. We did wish we could warm up the house a little more. We loved that the house had so many bathrooms. The only improvement would be to state that there are 5 bedrooms with en-suites."
Stunning waterfront villa with indoor pool and kids swing set and play area.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Exterior

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (32)
"Beautiful home, beautiful property! My family meets up annually and the house fit us perfectly. Plenty of room to spread out and congregate together. The home also provides so much to do with all the amenities! Thanks for the memories "
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Blake House Historic Estate with Private Inn

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"
Blake House Historic Estate with Private Inn
Exquisite 14,000 sq ft Waterfront Mansion with Pool
Exterior

Exquisite 14,000 sq ft Waterfront Mansion with Pool

Exquisite 14,000 sq ft Waterfront Mansion with Pool
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

'At Fells Point' CitySide - 'Tons better than a hotel!'
CitySide Living Room & Sofa Bed

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (185)
"The property is compact but cute. They have a door that slides across doorway between the bedroom and the living room that blocks noise from the outside. We did find the property chilly but when we contacted the owner, he had one of his staff come over, wait a few minutes for us outside, and provide us with space heaters that warmed the place up very effectively and quietly. We felt valued and cared for. I highly recommend this cozy little place and the people who manage it!"
The price is SARĀ 330
SARĀ 762 total
includes taxes & fees
25 Feb - 26 Feb
'At Fells Point' CitySide - 'Tons better than a hotel!'
Cass-N-Reel Luxury Houseboat
Exterior

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Chesapeake Houseboat Getaway on Kent Island, Maryland
Exterior

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.6 out of 10, Exceptional, (20)
"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
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.

Frequently asked questions

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