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Apartments in Chestertown for Rent

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Apartments in Chestertown

First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (102)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
$144 nightly
The price is $159
Oct 13 - Oct 14
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

9.6 out of 10, Exceptional, (19)
"The staff was great"
$110 nightly
The price is $117
Oct 9 - Oct 10
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
$282 nightly
The price is $311
Oct 9 - Oct 10
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Luxury Pool Loft sleeps 4
Pool

Luxury Pool Loft sleeps 4

10.0 out of 10, Exceptional, (3)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
$334 nightly
The price is $359
Oct 21 - Oct 22
Total with taxes and fees
Luxury Pool Loft sleeps 4
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, (7)
"This property was decorated beautifully. Roomy and functional. We enjoyed coffee on the rear deck. Neighborhood restaurants were great. We had great communication with our host. This trip far exceeded our expectations."
$195 nightly
The price is $225
Oct 9 - Oct 10
Total with taxes and fees
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (16)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
$260 nightly
The price is $287
Oct 10 - Oct 11
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Cozy Fells Point Gem / In The Heart of Fells Point
Marina

Cozy Fells Point Gem / In The Heart of Fells Point

9.8 out of 10, Exceptional, (197)
"Great place close to eveything"
$177 nightly
The price is $204
Oct 13 - Oct 14
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards
Smart TV

1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards

$281 nightly
The price is $325
Oct 9 - Oct 10
Total with taxes and fees
1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (79)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
$434 nightly
The price is $495
Oct 13 - Oct 14
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Hidden Fells Point Gem / Private Courtyard Patio
Marina

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!"
$177 nightly
The price is $204
Oct 13 - Oct 14
Total with taxes and fees
Hidden Fells Point Gem / Private Courtyard Patio
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.0 out of 10, Wonderful, (12)
"Property description is accurate, host is quickly responsive."
$326 nightly
The price is $372
Oct 19 - Oct 20
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Loved it"
Beata 1-night trip
Posted 1 day ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
429
Accommodation
87 Apartments
Lowest Price
$117
Highest Price
$495

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 8 apartments in Chestertown for your vacation.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
First Floor Studio Apartment in Historic Chestertown: Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. Historic Downtown Garden Oasis with Private Patio: Free WiFi, outdoor space, and separate dining areas are included.
How many apartments can I expect to find in Chestertown?
Expedia has 8 apartments to book in Chestertown.
What can I expect from the weather during my trip to Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What should I see and do in Chestertown?
Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Chestertown Dog Park and Urieville Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Rolphs Wharf Marina and Chestertown Historic District.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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Explore a world of travel with Expedia