
Pet Friendly Apartments for Rent in Chestertown, MD (41 Rentals)
Apartments for rent in Chestertown that love your dogs or cats as much as you do!


Chestertown Cove Apartments

Hopkins Point by OneWall

Seneca Bay Apartment Homes

Kings Mill Apartments and Townhomes

Woodsdale Apartments

The Greens Apartments and Townhomes
Cash 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.

Hartland Village Apartments

Beacon Pointe Apartments and Townhomes

Harborside Village Apartments
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.

Kingston Townhomes

Village Of Carrollwood

Perryman Station Senior Apartments, 62+
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.

73 Cattail Ln

903 Woodbridge Ct

821 Magnolia Ridge Ct

3922 Cutty Sark Rd
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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 | $1,331 | $777 | $1,650 |
| Chestertown 1 Bedroom Apartments | $1,548 | $668 | $2,539 |
| Chestertown 2 Bedroom Apartments | $1,766 | $950 | $2,900 |
| Chestertown 3 Bedroom Apartments | $1,927 | $1,050 | $3,200 |
| Chestertown 4 Bedroom Apartments | $2,285 | $1,989 | $2,400 |
Browse Top Apartments in Chestertown
See all Apartments in ChestertownExplore Chestertown
Chestertown, MD Local Guide
- Chestertown Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
Cheapest Pet Friendly Apartment Rentals in Chestertown , MD and nearby
The lowest priced Chestertown apartment at a property that allows pets is the One Bedroom One Bath 1 Bed Model at Hyde Park Apartments in the Hopewell Point neighborhood starting from $1,007. The second cheapest Chestertown Pet Friendly apartment is the 1x1 Premium - W&D Model at Edgewood Park Apartments, which is a 1 Bed starting at $1,130 in the Trimble Meadows neighborhood. Here are the most affordable Pet Friendly Chestertown apartments.
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Hyde Park Apartments | One Bedroom One Bath | $1,007 |
| Edgewood Park Apartments | 1x1 Premium - W&D | $1,130 |
| Seneca Bay Apartment Homes | Two Bedroom - 853 sqft | $1,320 |
| Verona at Middle River | Sicily | $1,324 |
| Winston's Choice Family Townhomes | UNIT A-INTERIOR UNIT | $1,339 |
| Kingston Townhomes | 3 Bedrooms 1 Bath | $1,573 |
| The Berkleigh | Studio-S2-Bird | $1,600 |
| Arbors Greenleigh | 1 Bed/1 Bath-A8-Dover | $1,650 |
| Riverside | 2 Bedroom | $1,759 |
| The Enclave at Box Hill | 1 Bed/1 Bath-A | $1,796 |
Don'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 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.
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
Getting Around Chestertown, MD
Walk Score®
47 / 100
Car-Dependent
Most errands require a car
Bike Score®
55 / 100
Bikeable
Some bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
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 Hopkins Point by OneWall listed at $1,175.
How much is the average rent for a Pet Friendly Chestertown Apartment?
The average rent for a Pet Friendly Apartment in Chestertown is $1,963.
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 $1,789 at The 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

Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.























