Apartments in Chestertown for Rent

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

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)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is ￥15,117
￥24,255 total
includes taxes & fees
Feb 23 - Feb 24
First Floor Studio Apartment in Historic Chestertown
Pool

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Chestertown
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."
United States
Jason
The price is ￥38,343
￥64,438 total
includes taxes & fees
Feb 21 - Feb 22
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
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 ￥20,615
￥29,136 total
includes taxes & fees
Feb 18 - Feb 19
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
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 ￥18,091
￥44,041 total
includes taxes & fees
Feb 18 - Feb 19
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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 ￥26,723
￥47,878 total
includes taxes & fees
Feb 18 - Feb 19
Waterfront Retreat with Private Dock and Beach
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 ￥29,013
￥56,749 total
includes taxes & fees
Feb 28 - Mar 1
18th Cent. Charm in Historic Downtown Annapolis
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, (201 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
The price is ￥8,857
￥30,513 total
includes taxes & fees
Feb 22 - Feb 23
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 ￥31,609
￥63,190 total
includes taxes & fees
Feb 19 - Feb 20
Waterfront Oasis of Annapolis Star
Exterior detail

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Historic District
9.6 out of 10, Exceptional, (27 reviews)
"Very clean, spacious, and located right by everything we wanted to visit. 10/10 would definitely stay here again with my family."
United States
David M.
The price is ￥32,067
￥56,749 total
includes taxes & fees
Feb 19 - Feb 20
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is ￥26,455
￥31,134 total
includes taxes & fees
Feb 27 - Feb 28
High Tide Haven Suite
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 ￥20,615
￥34,393 total
includes taxes & fees
Feb 23 - Feb 24
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
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 ￥21,346
￥62,850 total
includes taxes & fees
Mar 1 - Mar 2
Luxury Pool Loft sleeps 4
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"It is my favorite hotel during my stay al Balto/Wash"
Hilda 5-night trip
Posted 8 hours ago
Fairfield Inn & Suites by Marriott White Marsh

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
404
Accommodation
80 Apartments
Lowest Price
￥24,255
Highest Price
￥64,438

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 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.