Apartments in Chestertown for Rent

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Dec 12 - Dec 14
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Dec 19 - Dec 21
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Jan 2 - Jan 4
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Jan 30 - Feb 1

Apartments in Chestertown

Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 4 - Dec 5
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Apartment in Millington

9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
Dec 4 - Dec 5
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Apartment in Annapolis

10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Dec 4 - Dec 5
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Beach
Waterfront Retreat with Private Dock and Beach

Apartment in Worton

10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
$282 nightly
The price is $311
Dec 4 - Dec 5
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in Rock Hall

10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
$258 nightly
The price is $285
Dec 4 - Dec 5
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Apartment in Greektown

10.0 out of 10, Exceptional, (7)
"The house was clean and the beds were comfortable. "
United States
Karen B.
$195 nightly
The price is $225
Dec 4 - Dec 5
Total with taxes and fees
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Marina
Cozy Fells Point Gem / In The Heart of Fells Point

Apartment in Fells Point

9.8 out of 10, Exceptional, (200)
"Great place all around "
United States
Sophia F.
$174 nightly
The price is $201
Dec 9 - Dec 10
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
Apartment (4 Bedrooms) | Interior
Close to Hospital & White Marsh! Rosedale Townhome

Apartment in Nottingham

3.0 star property
$462 nightly
The price is $534
Dec 14 - Dec 15
Total with taxes and fees
Close to Hospital & White Marsh! Rosedale Townhome
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
"Amazing "
Breonah 2-night trip
Posted 3 days ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
378
Accommodation
93 Apartments
Lowest Price
$125
Highest Price
$534

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 5 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?
Here's a favorite apartment in the area to consider: Trendy Baltimore Townhome: 2 Mi to Downtown!: Located in Baltimore, 27.5 mi/44.3 km from Chestertown. Includes private balconies. Free parking and a marina are on site.
How many apartments can I expect to find in Chestertown?
Expedia has 5 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 Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.
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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