Holiday Homes in Chestertown

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Our top choices for Chestertown holiday homes

9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is NZ$458
includes taxes & fees
19 Jan - 20 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (8 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is NZ$603
includes taxes & fees
15 Jan - 16 Jan
Amazing Modern house with a full kitchen and parking
9.6 out of 10, Exceptional, (32 reviews)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is NZ$466
includes taxes & fees
18 Jan - 19 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
The price is NZ$473
includes taxes & fees
25 Jan - 26 Jan
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
8.0 out of 10, Very good, (2 reviews)
"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"
United States
James D.
The price is NZ$219
includes taxes & fees
18 Jan - 19 Jan
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Holiday Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is NZ$1,017
includes taxes & fees
15 Jan - 16 Jan
Neptune by the Water - Pet Friendly Fenced Yard
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is NZ$973
includes taxes & fees
15 Jan - 16 Jan
Charming Pet-Friendly Stay - Near Bay & Beaches.

Holiday Home in Bel Air

Hobbit House one of a kind home
10.0 out of 10, Exceptional, (8 reviews)
"We had a great stay! "
United States
Courtney H.
The price is NZ$496
includes taxes & fees
15 Jan - 16 Jan
Hobbit House one of a kind home
10.0 out of 10, Exceptional, (8 reviews)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is NZ$768
includes taxes & fees
27 Jan - 28 Jan
HGTV quality, private guest suite, country getaway with hot tub & fire pit
2.0 star property
The price is NZ$913
includes taxes & fees
19 Jan - 20 Jan
Heated Pool • Private Backyard • Home Theater

Holiday Home in Upper Fells Point

Johns Hopkins Historic Renovated home - Location!
9.4 out of 10, Exceptional, (14 reviews)
"Location was perfect and the place was great"
United States
Sharon P.
Johns Hopkins Historic Renovated home - Location!
2.0 star property
The price is NZ$226
includes taxes & fees
1 Feb - 2 Feb
Spacious Private 2BR Suite in Abingdon with Separate Entrance
9.4 out of 10, Exceptional, (36 reviews)
"Just as advertised. Clean and quiet."
United States
Robert B.
The price is NZ$554
includes taxes & fees
20 Jan - 21 Jan
Large 2 bedroom house with private parking in a nice neighborhood
10.0 out of 10, Exceptional, (20 reviews)
"We enjoyed this property so much that we stayed here again just 4 months later."
United States
Kim C.
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
9.6 out of 10, Exceptional, (5 reviews)
"Everything was great, easy check in and simple and clean space!!! Amazing thank you"
United States
michael t.
The price is NZ$594
includes taxes & fees
5 Feb - 6 Feb
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
9.6 out of 10, Exceptional, (94 reviews)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"
United States
Edward J.
The price is NZ$352
includes taxes & fees
18 Jan - 19 Jan
Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is NZ$723
includes taxes & fees
27 Jan - 28 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (73 reviews)
"Great location!"
United States
Burton S.
The price is NZ$560
includes taxes & fees
20 Jan - 21 Jan
Cozy 2br home w/ parking in downtown Annapolis
8.6 out of 10, Excellent, (8 reviews)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
United States
Jeffrey S.
The price is NZ$592
includes taxes & fees
19 Jan - 20 Jan
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Holiday Home in Kent County

High Tide Haven Suite
The price is NZ$346
includes taxes & fees
25 Jan - 26 Jan
High Tide Haven Suite
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

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
327
Accommodation
485 Holiday Homes
Lowest Price
NZ$219
Highest Price
NZ$1,017