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Villas in Chestertown

Compare 3 Villas in Chestertown with updated reviews, rates, and availability.

Balcony
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Property grounds
Stunning waterfront villa with indoor pool and kids swing set and play area.
10.0 out of 10, Exceptional, (3)
"Great weekend with friends in this beautiful home. Plenty of space for the 14 of us. Indoor pool/bar area was the perfect space for us to hang out together."
Stunning waterfront villa with indoor pool and kids swing set and play area.
Property grounds
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
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View from property
Blake House Historic Estate with Private Inn
10.0 out of 10, Exceptional, (16)
"We had a wonderful time at Blake House with our extended family. Lots of room for everyone and we all loved the property, pool and offerings. The elevated welcome package, yoga session (for 11 of us!) and Chef Erica and team dinner were such incredible experiences. It was a perfect vacation. Highly recommend!!"
Blake House Historic Estate with Private Inn
Fridge, microwave, oven, stovetop
Exquisite 14,000 sq ft Waterfront Mansion with Pool
Exquisite 14,000 sq ft Waterfront Mansion with Pool
View from property
Come enjoy our luxurious 10,000 sq
9.2 out of 10, Wonderful, (10)
"We are two families with small kids (ages 1-5) from the DC area, and we thoroughly enjoyed our weekend. It took us exactly 2 hours to drive from the DC suburbs which made it very doable as a weekend trip. Instacart delivered groceries, which we appreciated - at other more rural VRBOs that we’ve stayed in it requires 30+ minutes round trip to the nearest store if we forget something, so it was nice to avoid that. The pool was in great condition and we swam in it 3x a day, which thoroughly tired...
Come enjoy our luxurious 10,000 sq
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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.

Other property types in Chestertown

Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (51)
"Had an excellent time at this beautiful and secluded property on the Chester River. Although very private and a lot of outside space to roam, we were still very close to all that Chestertown has to offer. So, it was the best of both worlds. Plenty of amazing scenery and wildlife to enjoy around the property, and Beth is an excellent communicator. If you're a wine drinker, check out a number of close-by wineries like: Casa Carmen, Bu-De, Broken Spoke and Crow Vineyards. Would highly recommend...
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is $629
$1,417 total
includes taxes & fees
Jun 4 - Jun 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Beach nearby, sun loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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.

Chestertown Villas information

Number of reviews
34
Accommodation
3 Villas
Lowest Price
Highest Price

Frequently asked questions

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Use Expedia to find your dream villa in Chestertown. Taking the kids on a break? Take advantage of our filters to look for stays with perks like a pool. If you have a budget in mind, click on how much you’d like to spend and the star rating of the property. We’ll help you find the right place in tune with your taste and style.
How can I find cheap villas in Chestertown?
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What is there to do near my villa in Chestertown?
The ultimate travel accessory is a well-planned schedule. Historical Society of Kent County Maryland is an excellent place to begin your exploration of Chestertown.

Recent reviews of Chestertown hotels
Expedia verified reviews

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

5/5 Excellent
Great Room
"The room was spotless. The front desk was helpful. The complementary breakfast was delicious. I would definitely stay there again. "
A verified traveler stayed at Fairfield Inn & Suites by Marriott White Marsh
Posted 16 hours ago
Fairfield Inn & Suites by Marriott White Marsh