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Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select Chestertown Vacation Homes

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

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

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is CA $110
CA $381 total
includes taxes & fees
Aug 24 - Aug 25
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Amazing Modern house with a full kitchen and parking
Dining

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 CA $150
CA $378 total
includes taxes & fees
Aug 31 - Sep 1
Amazing Modern house with a full kitchen and parking
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is CA $145
CA $424 total
includes taxes & fees
Aug 27 - Aug 28
Relax on Kent Island in 3 Bedroom Home w/Waterview
Abingdon Haven Hideaway
Fridge, microwave, oven, stovetop

Abingdon Haven Hideaway

7.0 out of 10, Good, (2)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
The price is CA $162
CA $534 total
includes taxes & fees
Sep 3 - Sep 4
Abingdon Haven Hideaway
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Smart TV, fireplace

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 CA $125
CA $174 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Fridge, microwave, oven, stovetop

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

2.0 star property
10.0 out of 10, Exceptional, (2)
"Crystal responded very quickly (within an hour) to provide me with check-in instructions. The place looks exactly like the pictures, smelled amazing, and was very clean. I had a small get together for my partner’s birthday and we played pool as well as card games at the poker table. Everyone kept saying how much fun they were having at her place so I definitely recommend. 10/10 Crystal thank you so much!"
The price is CA $191
CA $352 total
includes taxes & fees
Sep 3 - Sep 4
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Modern New Suite Close to US Capital and BWI Airport
Fridge, microwave, oven, stovetop

Modern New Suite Close to US Capital and BWI Airport

10.0 out of 10, Exceptional, (1)
"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 CA $97
CA $205 total
includes taxes & fees
Aug 27 - Aug 28
Modern New Suite Close to US Capital and BWI Airport
Charming 2-bedroom apartment in fantastic Overlea with AC
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom apartment in fantastic Overlea with AC

The price is CA $173
CA $316 total
includes taxes & fees
Sep 3 - Sep 4
Charming 2-bedroom apartment in fantastic Overlea with AC
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
1 bedroom, iron/ironing board, WiFi, bed sheets

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

The price is CA $132
CA $333 total
includes taxes & fees
Sep 18 - Sep 19
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Interior

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

10.0 out of 10, Exceptional, (2)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
The price is CA $300
CA $424 total
includes taxes & fees
Sep 3 - Sep 4
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Charming Pet-Friendly Stay - Near Bay & Beaches.
Interior

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (3)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is CA $262
CA $704 total
includes taxes & fees
Aug 25 - Aug 26
Charming Pet-Friendly Stay - Near Bay & Beaches.
Hidden Fells Point Gem / Private Courtyard Patio
Marina

Hidden Fells Point Gem / Private Courtyard Patio

9.6 out of 10, Exceptional, (87)
"Property is clean and efficiently designed, tastefully decorated and located in a safe, walkable area.I would recommend this location to anyone wanting to visitBaltimore."
The price is CA $86
CA $284 total
includes taxes & fees
Aug 25 - Aug 26
Hidden Fells Point Gem / Private Courtyard Patio
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Fridge, microwave, oven, stovetop

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

10.0 out of 10, Exceptional, (4)
"The house was clean and the beds were comfortable. "
The price is CA $187
CA $296 total
includes taxes & fees
Sep 3 - Sep 4
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

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

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is CA $347
CA $581 total
includes taxes & fees
Aug 27 - Aug 28
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Hobbit House one of a kind home
Property grounds

Hobbit House one of a kind home

10.0 out of 10, Exceptional, (5)
"Our family had a fantastic weekend here. The house fit our needs and was very relaxing and enjoyable."
The price is CA $165
CA $430 total
includes taxes & fees
Aug 24 - Aug 25
Hobbit House one of a kind home
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

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

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is CA $274
CA $619 total
includes taxes & fees
Sep 1 - Sep 2
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop

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 CA $286
CA $541 total
includes taxes & fees
Sep 22 - Sep 23
Bayside Cottage steps from Rock Hall Harbor
Neptune by the Water - Pet Friendly Fenced Yard
Fridge, microwave, oven, stovetop

Neptune by the Water - Pet Friendly Fenced Yard

9.6 out of 10, Exceptional, (10)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is CA $260
CA $769 total
includes taxes & fees
Aug 27 - Aug 28
Neptune by the Water - Pet Friendly Fenced Yard
Exclusive Sunken Living Room Soaring Exposed Brick
Interior

Exclusive Sunken Living Room Soaring Exposed Brick

10.0 out of 10, Exceptional, (5)
"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...
The price is CA $236
CA $525 total
includes taxes & fees
Aug 24 - Aug 25
Exclusive Sunken Living Room Soaring Exposed Brick
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (46)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is CA $277
CA $413 total
includes taxes & fees
Sep 3 - Sep 4
BAYSIDE BUNGALOW
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"All the staff was very friendly and accommodating, and even treated us to a bottle of wine and some pastries for our anniversary"
Donna 1-night trip
Posted 2 days ago
Historic Inns of Annapolis