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Vacation Homes in Chestertown

Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is ¥13,595
¥41,538 total
includes taxes & fees
Oct 19 - Oct 20
Relax on Kent Island in 3 Bedroom Home w/Waterview
Amazing Modern house with a full kitchen and parking
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
The price is ¥27,214
¥53,083 total
includes taxes & fees
Oct 19 - Oct 20
Amazing Modern house with a full kitchen and parking
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.6 out of 10, Exceptional, (30)
"Nice and peaceful stay for a quick local getaway. "
The price is ¥15,081
¥41,789 total
includes taxes & fees
Oct 21 - Oct 22
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
2.0 star property
9.6 out of 10, Exceptional, (4)
"Everything was great, easy check in and simple and clean space!!! Amazing thank you"
The price is ¥14,968
¥31,259 total
includes taxes & fees
Oct 16 - Oct 17
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (88)
"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!"
The price is ¥9,374
¥30,910 total
includes taxes & fees
Oct 15 - Oct 16
Hidden Fells Point Gem / Private Courtyard Patio
Chesapeake Bay Harbor View in a central location to events/restaurants
2.5 star property
The price is ¥34,018
¥41,187 total
includes taxes & fees
Oct 15 - Oct 16
Chesapeake Bay Harbor View in a central location to events/restaurants
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (5)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
The price is ¥29,065
¥77,590 total
includes taxes & fees
Oct 15 - Oct 16
Charming Pet-Friendly Stay - Near Bay & Beaches.
Modern New Suite Close to US Capital and BWI Airport
7.0 out of 10, Good, (2)
"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "
The price is ¥10,205
¥21,803 total
includes taxes & fees
Oct 15 - Oct 16
Modern New Suite Close to US Capital and BWI Airport
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is ¥26,458
¥54,328 total
includes taxes & fees
Oct 21 - Oct 22
Bayside Cottage steps from Rock Hall Harbor
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (12)
"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. "
The price is ¥37,798
¥62,182 total
includes taxes & fees
Oct 17 - Oct 18
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
High Tide Haven Suite
The price is ¥26,194
¥30,346 total
includes taxes & fees
Oct 20 - Oct 21
High Tide Haven Suite
HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (6)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
The price is ¥30,024
¥67,834 total
includes taxes & fees
Oct 27 - Oct 28
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (28)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
The price is ¥19,655
¥49,294 total
includes taxes & fees
Nov 3 - Nov 4
Large 2 bedroom house with private parking in a nice neighborhood
The Hideaway Spot- Waterfront w/ Dock on Long Cove
8.4 out of 10, Very Good, (7)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
The price is ¥16,465
¥53,068 total
includes taxes & fees
Oct 16 - Oct 17
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Close to Hospital & White Marsh! Rosedale Townhome
2.0 star property
The price is ¥32,052
¥97,442 total
includes taxes & fees
Oct 17 - Oct 18
Close to Hospital & White Marsh! Rosedale Townhome
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
8.0 out of 10, Very Good, (1)
"The property itself was very clean and cozy, and having our own private entry was also very nice. Towels and shower supplies were provided, and the bed was nice and comfortable. The host was also very kind and answered any questions we had. However, every morning we were woken up at around 7:30 am by someone (I assume children) stomping around right over our heads. There were also times we didn't really feel comfortable hanging out to watch TV in the living room area, because we could hear the...
The price is ¥13,607
¥18,959 total
includes taxes & fees
Oct 15 - Oct 16
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (145)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is ¥48,849
¥90,884 total
includes taxes & fees
Oct 15 - Oct 16
5-bedroom vacation home 5 minutes from historic Charlestown
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
10.0 out of 10, Exceptional, (4)
"The house was even better than I anticipated! It was very clean, quiet and comfy. The beds were amazing and we got the best nights sleep! Location was perfect for Ripken Experience. The owner was very helpful and quick to respond to my messages. "
The price is ¥25,309
¥38,045 total
includes taxes & fees
Oct 20 - Oct 21
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
John’s Hopkins Downtown free parking 3 bedroom 3 bth sleeps 8 rooftop deck
9.4 out of 10, Exceptional, (3)
"We had a wonderful stay at Deanna’s house, everything was clean and easy to get in with self instructions. We liked that the house was also close enough to inner harbor. The owner had great communication too, thank you we’ll plan to stay again soon!! "
The price is ¥25,717
¥71,963 total
includes taxes & fees
Oct 15 - Oct 16
John’s Hopkins Downtown free parking 3 bedroom 3 bth sleeps 8 rooftop deck
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
The price is ¥13,909
¥35,898 total
includes taxes & fees
Oct 30 - Oct 31
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
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

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Chestertown Vacation Homes information

Number of reviews
325
Accommodation
483 Vacation Homes
Lowest Price
¥18,959
Highest Price
¥90,884