
Apartments for Rent near Chestertown, MD with Swimming Pool (14 Rentals)


Total Monthly Price
Aberdeen Proving Ground on Post Housing

Seven Oaks Townhomes

Eagle Rock Apartments at Belcamp

Seneca Bay Apartment Homes

Woodsdale Apartments

Beacon Pointe Apartments and Townhomes
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

Essex Park Apartments and Townhomes

Chesapeake Village Apartments

Total Monthly Price
The Berkleigh

Total Monthly Price
Arbors Greenleigh

Riverside

Kingston Townhomes

Total Monthly Price
Enclave at Box Hill
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
What are amenity fees and are they optional? This guide breaks down everything you need to know about apartment amenity fees, including when you can opt out and how you might be able to lower your rent.
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 | $1,024 | $852 | $1,260 |
| Chestertown 1 Bedroom Apartments | $1,567 | $765 | $2,256 |
| Chestertown 2 Bedroom Apartments | $1,697 | $950 | $2,956 |
| Chestertown 3 Bedroom Apartments | $1,943 | $1,050 | $3,055 |
| Chestertown 4 Bedroom Apartments | $2,239 | $1,974 | $2,400 |
Browse Top Apartments 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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Pet Friendly Lifestyle
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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 Chestertown Apartments with Swimming Pool
What is the Cheapest Swimming Pool apartment in Chestertown?
Currently the most affordable Apartment in Chestertown with Swimming Pool is at Essex Park Apartments and Townhomes listed at $996.
How much is the average rent for Chestertown Apartments with Swimming Pool?
The average rent for a Apartment in Chestertown with Swimming Pool is $1,874.
What is the largest Chestertown Apartment for rent with Swimming Pool?
Today's Apartment with Swimming Pool and the most square footage in Chestertown is a 1,780 square feet unit starting from $1,887 at Enclave at Box Hill.
What is the average size for Chestertown Apartments for rent with Swimming Pool?
The average size for a rental with Swimming Pool in Chestertown is currently at 708 sq ft.
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

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.