
Pet Friendly Apartments for Rent in Chestertown, MD (49 Rentals)
Apartments for rent in Chestertown that love your dogs or cats as much as you do!


Chestertown Cove Apartments

Hopkins Point by OneWall

Total Monthly Price
Harborside Village Apartments

Seven Oaks Townhomes

Eagle Rock Apartments at Belcamp

Middle River Overlook

Seneca Bay Apartment Homes

Woodsdale Apartments
Pet-Friendly Renting: Everything You Need to Know Before You Move
Finding a pet-friendly apartment is with ease. Learn how to navigate the rental process as a pet owner and build trust with your landlord from day one.

Hyde Park Apartments

Kings Mill Apartments and Townhomes

Hartland Village Apartments

The Greens Apartments and Townhomes

Total Monthly Price
Aberdeen Proving Ground on Post Housing

Beacon Pointe Apartments and Townhomes

Essex Park Apartments and Townhomes

Chesapeake Village Apartments

Total Monthly Price
The Berkleigh
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.

Total Monthly Price
Arbors Greenleigh

Carriage Court Apartments

Riverside

Fox Run Apartments

Magnolia Farms

Kingston Townhomes

Village Of Carrollwood

Windsor Valley Apartments
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

The Waldon

Holly Oaks

Foxridge Townhomes

Total Monthly Price
Enclave at Box Hill

The Willows at Cecilton

Harford Commons

The Promenade at Red Apple Town Center

215 Thompson Ave
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

903 Woodbridge Ct

28 Ebbing Ct

3924 Cutty Sark Rd

10 Blackfoot Ct

5 Homeland Ave

314 Old Post Rd

470 Washington St

4927 Bristle Cone Cir

Edgewood Park Apartments
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

Merion Village, 62+ Living

Stansbury Manor

Perryman Station Senior Apartments, 62+

Winston's Choice Family Townhomes
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 | $969 | $687 | $1,048 |
| Chestertown 1 Bedroom Apartments | $1,521 | $765 | $2,118 |
| Chestertown 2 Bedroom Apartments | $1,762 | $950 | $2,956 |
| Chestertown 3 Bedroom Apartments | $2,052 | $1,050 | $3,264 |
| Chestertown 4 Bedroom Apartments | $2,239 | $1,974 | $2,400 |
Browse Top Apartments in Chestertown
See all Apartments in ChestertownExplore Chestertown
Chestertown, MD Local Guide
- Chestertown Neighborhoods
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Cheapest Pet Friendly Apartment Rentals in Chestertown , MD and nearby
The lowest priced Chestertown apartment at a property that allows pets is the Studio Studio Model at The Greens Apartments and Townhomes in the Hopewell Point neighborhood starting from $687. The second cheapest Chestertown Pet Friendly apartment is the Studio 1 Bathroom Model at Hyde Park Apartments, which is a Studio starting at $988 in the Hopewell Point neighborhood. Here are the most affordable Pet Friendly Chestertown apartments.
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| The Greens Apartments and Townhomes | Studio | $687 |
| Hyde Park Apartments | Studio 1 Bathroom | $988 |
| Seneca Bay Apartment Homes | One Bedroom | $1,040 |
| Middle River Overlook | 2BD/1BA | $1,119 |
| Magnolia Farms | 2 Bedroom Apt | $1,190 |
| Arbors Greenleigh | 1 Bed/1 Bath Jr-A9-Beckley | $1,623 |
| Kingston Townhomes | 3 Bedrooms 1 Bath | $1,682 |
| Foxridge Townhomes | 3 Bedrooms 1 Bath | $1,723 |
| Riverside | The Annapolitan | $1,849 |
| The Berkleigh | 1 Bed/1 Bath-A3-Magothy | $1,946 |
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 ArticleReal 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.
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 Pet Friendly Chestertown Apartments
What is the Cheapest Pet Friendly apartment in Chestertown?
Currently the most affordable Pet Friendly Apartment in Chestertown is at Chesapeake Village Apartments listed at $997.
How much is the average rent for a Pet Friendly Chestertown Apartment?
The average rent for a Pet Friendly Apartment in Chestertown is $1,895.
What is the largest Pet Friendly Chestertown Apartment for rent?
Today's Pet Friendly apartment with the most square footage in Chestertown is a 1,780 square feet unit starting from $1,609 at Enclave at Box Hill.
What is the average size for Chestertown Pet Friendly Apartments for rent?
The average size for a Pet Friendly rental in Chestertown is currently at 712 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

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.

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.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

