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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Chestertown apartments

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Everything was clean and neat and welcoming "
United States
Iriana J.
The price is CA $135
CA $217 total
includes taxes & fees
Mar 5 - Mar 6
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (13 reviews)
"Great experience"
United States
David P.
The price is CA $234
CA $472 total
includes taxes & fees
Feb 28 - Mar 1
18th Cent. Charm in Historic Downtown Annapolis
Living area

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is CA $185
CA $262 total
includes taxes & fees
Mar 1 - Mar 2
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is CA $239
CA $430 total
includes taxes & fees
Mar 1 - Mar 2
Waterfront Retreat with Private Dock and Beach
Exterior

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is CA $93
CA $171 total
includes taxes & fees
Mar 24 - Mar 25
Guest Suite for up to 2 in a Victorian on the Chester River
Beach

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $161
CA $392 total
includes taxes & fees
Feb 28 - Mar 1
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Marina

Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (202 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
The price is CA $85
CA $281 total
includes taxes & fees
Mar 18 - Mar 19
Cozy Fells Point Gem / In The Heart of Fells Point
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is CA $283
CA $563 total
includes taxes & fees
Feb 28 - Mar 1
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop

Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is CA $171
CA $532 total
includes taxes & fees
Feb 28 - Mar 1
Luxury Pool Loft sleeps 4
Interior

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

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.6 out of 10, Exceptional, (9 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is CA $185
CA $313 total
includes taxes & fees
Mar 8 - Mar 9
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is CA $237
CA $277 total
includes taxes & fees
Mar 1 - Mar 2
High Tide Haven Suite
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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Very clean hotel, friendly staff, and near restaurants. Perfect place for us to stay while on the road."
Bridget 1-night trip
Posted 3 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
467
Accommodation
80 Apartments
Lowest Price
CA $171
Highest Price
CA $563

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 6 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 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access: Free WiFi, private balconies, and Smart TVs are included. Access to onsite laundry facilities is available on site.
How many apartments can I expect to find in Chestertown?
Expedia has 6 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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