
3 Bedroom Homes for Rent in Chestertown, MD (20 Rentals)


1523 Charlestown Dr

962 Topview Dr

980 Topview Dr

1857 Simons Ct

410 Melvin Ave
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

1250 Independence Square

106 Johnstown Ln

313 Winterberry Dr

502 Brighton Pl

2902 Indian Summer Ct

7199 Cunning Cir
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

82 Basin Rd

11415 Eastern Ave

4307 Greys Run Cir

3184 Ebbtide Dr

29 Queen Mary Ct

106 Blenny Ln
Renting Smart: Lease Basics Every Renter Needs
Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

2513 Barrison Point Rd

2926 WATERFRONT Way
Chestertown, MD Local Guide

How much does it cost to rent a home in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chestertown 2 Bedroom Homes for Rent | $1,767 | $1,095 | $2,500 |
| Chestertown 3 Bedroom Homes for Rent | $2,396 | $1,195 | $4,500 |
| Chestertown 4 Bedroom Homes for Rent | $2,495 | $2,100 | $3,275 |
| Chestertown 5 Bedroom Homes for Rent | $2,395 | $2,395 | $2,395 |
Browse Top Homes for Rent in Chestertown
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Chestertown, MD Local Guide
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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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Among cities in Maryland for Apartment listings with Pet Friendly Amenities.
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Remember the 3 Rules of Real Estate:Location, Location, Location!
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See the most popular apartments and homes in Chestertown, MD
Frequently Asked Questions about Chestertown
What type of rentals are currently available in Chestertown?
There are currently 57 Apartments for Rent in Chestertown, MD with pricing that ranges from $677 to $3,624. There are also 36 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $995 to $4,500.
What is the current price range for Rental Homes in Chestertown?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestertown ranges from $995 to $4,500 with an average monthly rent of $2,060.
How much are larger Three and Four Bedroom Rentals in Chestertown?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestertown range from $1,050 to $3,624, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,195 to $4,500. Four Bedroom Single-Family rentals are also available starting from $2,100 and Four Bedroom Apartments start at $1,954.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Articles, How-To's, and Tips

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.