Apartments in Chestertown for Rent

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chestertown apartments

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Every thing was great"
United States
lesia k.
The price is ¥15,701
¥25,192 total
includes taxes & fees
Apr 15 - Apr 16
First Floor Studio Apartment in Historic Chestertown

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (28 reviews)
"Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!""
United States
Maggie D.
The price is ¥52,645
¥77,476 total
includes taxes & fees
Apr 4 - Apr 5
Newly restored apartment in the heart of Chestertown

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 ¥10,848
¥19,954 total
includes taxes & fees
Apr 8 - Apr 9
Guest Suite for up to 2 in a Victorian on the Chester River

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 ¥24,089
¥33,144 total
includes taxes & fees
Apr 28 - Apr 29
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

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, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is ¥19,782
¥46,510 total
includes taxes & fees
Apr 9 - Apr 10
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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, (10 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is ¥21,537
¥35,931 total
includes taxes & fees
Apr 5 - Apr 6
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

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, (203 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
The price is ¥10,369
¥33,166 total
includes taxes & fees
Apr 14 - Apr 15
Cozy Fells Point Gem / In The Heart of Fells Point

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 ¥27,918
¥50,019 total
includes taxes & fees
Apr 20 - Apr 21
Waterfront Retreat with Private Dock and Beach

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 ¥39,484
¥74,292 total
includes taxes & fees
Apr 4 - Apr 5
Waterfront Oasis of Annapolis Star

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Great experience"
United States
David P.
The price is ¥38,128
¥68,381 total
includes taxes & fees
Apr 19 - Apr 20
18th Cent. Charm in Historic Downtown Annapolis

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is ¥27,477
¥31,664 total
includes taxes & fees
Apr 15 - Apr 16
High Tide Haven Suite

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
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 ¥19,825
¥61,654 total
includes taxes & fees
Apr 8 - Apr 9
Pool Loft Suite | Bay Access & Beach Passes

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
The price is ¥18,378
¥32,281 total
includes taxes & fees
Apr 14 - Apr 15
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
309
Accommodation
80 Apartments
Lowest Price
¥19,954
Highest Price
¥77,476

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?
Here are some of the more popular apartments in the area to choose from: 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. 18th Cent. Charm in Historic Downtown Annapolis: Located 28 mi/45.1 km away in Annapolis. Free WiFi, private patios, and fireplaces are included. Onsite laundry facilities and a game room are on site. Cozy Fells Point Gem / In The Heart of Fells Point: It's situated in Baltimore, 28.3 mi/45.5 km away. Includes free WiFi and Smart TVs. Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located 21.4 mi/34.4 km away in Pasadena. Free WiFi and Smart TVs are included. Access to an outdoor pool is available on site. Waterfront Oasis of Annapolis Star: Located in Annapolis, 25.8 mi/41.5 km from Chestertown. Includes a private pool, free WiFi, and fireplaces. Access to an outdoor pool 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 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.