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Vacation Homes in Chestertown

Historic Downtown Luxury • USNA • Waterfront

Historic District
$576 nightly
The price is $586
Nov 9 - Nov 10
Total with taxes and fees
Historic Downtown Luxury • USNA • Waterfront

Small House on Gentleman’s Farm

Bel Air
10.0 out of 10, Exceptional, (12)
"Great little getaway, very clean, and the bedding was so comfy! "
United States
Joan F.
$293 nightly
The price is $295
Dec 2 - Dec 3
Total with taxes and fees
Small House on Gentleman’s Farm

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
$264 nightly
The price is $280
Nov 16 - Nov 17
Total with taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Stevensville
9.6 out of 10, Exceptional, (31)
"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
$246 nightly
The price is $261
Nov 12 - Nov 13
Total with taxes and fees
❤️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
Berea
9.6 out of 10, Exceptional, (4)
"Crystal was a wonderful host with great communication! The check in process was simple and the house was tidy; would definitely recommend. "
United States
Mekiyah H.
$171 nightly
The price is $197
Nov 10 - Nov 11
Total with taxes and fees
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

Large 2 bedroom house with private parking in a nice neighborhood

Arnold
9.4 out of 10, Exceptional, (31)
"This was a great place to stay with everything you needed. I loved the furniture in the house and it was well decorated, not to mention the neighborhood was quiet and close to all these good restaurants. Parking was a breeze for us since we drove in two cars. We parked in the wrap around driveway. There is a small fenced in back yard so it was perfect to let the dog run around and do his business. The host was great and couldn’t have asked for a better stay. "
United States
Mateusz K.
$267 nightly
The price is $304
Nov 9 - Nov 10
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

Hidden Fells Point Gem / Private Courtyard Patio

Fells Point
9.6 out of 10, Exceptional, (89)
"Lenny’s apartment was the perfect base for our Baltimore visit! It’s just a short walk to the water where there are shops, restaurants and bars. The space is cozy, has everything you need to make meals and was very clean. Lenny was quick to respond to questions and was very accommodating. Thanks for a great stay! "
United States
Maureen S.
$174 nightly
The price is $201
Nov 10 - Nov 11
Total with taxes and fees
Hidden Fells Point Gem / Private Courtyard Patio

Hobbit House one of a kind home

Bel Air
10.0 out of 10, Exceptional, (7)
"We had a great stay! "
United States
Courtney H.
$303 nightly
The price is $305
Nov 17 - Nov 18
Total with taxes and fees
Hobbit House one of a kind home

Modern New Suite Close to US Capital and BWI Airport

Pasadena
7.0 out of 10, Good, (2)
"Great location but horrible noise level AT the property as well as someone else’s hair in the carpets in our room. The property manager communicated well, however, we shouldn’t have had to ask on more than one occasion for his tenant to stop playing his game so loudly at night. We also shouldn’t have had someone else hair in our room and on our belongings. Would not stay again. "
United States
Lenny J.
$129 nightly
The price is $147
Dec 6 - Dec 7
Total with taxes and fees
Modern New Suite Close to US Capital and BWI Airport

The Hideaway Spot- Waterfront w/ Dock on Long Cove

Glen Burnie
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."
United States
Jeffrey S.
$306 nightly
The price is $349
Nov 17 - Nov 18
Total with taxes and fees
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Glen Burnie
8.0 out of 10, Very Good, (2)
"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.
$110 nightly
The price is $125
Nov 8 - Nov 9
Total with taxes and fees
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Exclusive Sunken Living Room Soaring Exposed Brick

Patterson Place
10.0 out of 10, Exceptional, (6)
"Our stay was absolutely wonderful! The amenities that Matthew provided were great -- there were mints, lollypops, and granola bars for each of us upon arrival. The space is incredible! From the Master Suite with a king-sized bed that was adjustable to the other bedrooms that were comfortable and cozy. Also, we loved the small details, like the beautiful paintings and decorations, plus the "Baltimore Bucket List" to check-off. Everything was clean and neat, and anytime we had a question, Matthew...
United States
Julie B.
$267 nightly
The price is $308
Nov 16 - Nov 17
Total with taxes and fees
Exclusive Sunken Living Room Soaring Exposed Brick

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville
9.6 out of 10, Exceptional, (12)
"I was impressed with how spacious and clean the house was."
United States
Susan M.
$395 nightly
The price is $419
Nov 10 - Nov 11
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Aberdeen
$215 nightly
The price is $228
Nov 9 - Nov 10
Total with taxes and fees
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

High Tide Haven Suite

Kent County
$193 nightly
The price is $200
Nov 9 - Nov 10
Total with taxes and fees
High Tide Haven Suite

Neptune by the Water - Pet Friendly Fenced Yard

Cape Saint Claire
9.8 out of 10, Exceptional, (11)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
$472 nightly
The price is $502
Nov 12 - Nov 13
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville
10.0 out of 10, Exceptional, (7)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
$420 nightly
The price is $445
Nov 17 - Nov 18
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (1)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
$257 nightly
The price is $272
Nov 8 - Nov 9
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants

New! Stylish downtown home w/awesome outdoor area!

Stevensville
9.8 out of 10, Exceptional, (26)
"Great location and property for our purpose, friendly and accommodating owner."
United States
Chris
New! Stylish downtown home w/awesome outdoor area!

Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

Canton
9.8 out of 10, Exceptional, (65)
"This was the best VRBO experience we've ever had. The property was exactly as described, the location was fantastic, and the rental property was the best stocked property we've ever experienced. Absolutely perfect?"
United States
Bill H.
$242 nightly
The price is $280
Nov 18 - Nov 19
Total with taxes and fees
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
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 Vacation Homes information

Number of reviews
305
Accommodation
483 Vacation Homes
Lowest Price
$125
Highest Price
$502

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