
Cheap 1 Bedroom Apartments for Rent in Chestertown, MD from $765 (31 Rentals)


Brookmeadow Apartments

Windsor Valley Apartments

Kings Mill Apartments and Townhomes

The Greens Apartments and Townhomes

Hartland Village Apartments

Essex Park Apartments and Townhomes
Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Create a productive work-from-home apartment setup, even in a small space or studio. Discover layout ideas, desk solutions, and organization tips that actually work.

Hopkins Point by OneWall

Seneca Bay Apartment Homes

Hyde Park Apartments

Chesapeake Village Apartments

Fox Run Apartments

Harford Commons

Aberdeen Parke Apartments
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

Woodsdale Apartments

Annhurst (MD)

Beacon Pointe Apartments and Townhomes

The Waldon

Seven Oaks Townhomes

Total Monthly Price
Harborside Village Apartments

ReNew Belcamp
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

Riverside

Perryman Station Senior Apartments, 62+

Center Park Apartments

Brookside Station Apartments

The Village at Slippery Hill Senior Apartments- 62+

1304 2nd Rd

Edgewood Park Apartments
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.

Merion Village, 62+ Living

Stansbury Manor

722 Church Hill Rd
Chestertown, MD Local Guide

How much does it cost to rent an apartment in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chestertown Studio Apartments | $1,082 | $802 | $1,656 |
| Chestertown 1 Bedroom Apartments | $1,494 | $765 | $2,449 |
| Chestertown 2 Bedroom Apartments | $1,758 | $950 | $2,873 |
| Chestertown 3 Bedroom Apartments | $2,055 | $1,050 | $3,128 |
| Chestertown 4 Bedroom Apartments | $2,253 | $2,009 | $2,400 |
Explore Chestertown
Chestertown, MD Local Guide
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10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read ArticleDon't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Pet Friendly Lifestyle
Ranked #
Among cities in Maryland for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
Pet Friendly
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Chestertown, MD Rentals by Map
See the most popular apartments and homes in Chestertown, MD
Frequently Asked Questions about Cheap Chestertown Apartments
How much is rent for a Cheap One Bedroom Chestertown Apartment?
The lowest price for a Cheap One Bedroom Chestertown Apartment is $765 at Windsor Valley Apartments.
What is the lowest price for a Cheap Two Bedroom Chestertown Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Chestertown is starting from $765 at Windsor Valley Apartments.
What is the most affordable Chestertown Three Bedroom Apartment?
The best deal on a cheap Chestertown Three Bedroom Apartment rental is at Windsor Valley Apartments and starts from $765.
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

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.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.