
Apartments for Rent in Chestertown, NY Under $2,000 (48 Rentals)


The Paddocks of Saratoga

The Hamlet at Saratoga Springs

Enclave 50

Perennial

The Ellsworth
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.

Winner's circle

Schermerhorn - South Glens Falls

Steeplechase at Malta

English Village Apartments

Williamsburg Court
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.

Glen Street Associates

14 Bowman St

Bridgewater Apartments

Regency Park North

Skidmore Apartments

Whispering Pines

Reserve at Saratoga Springs

The Landings at Kingsbury

Robert Gardens North

Canfield Apartments, LLC
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.

11 Keyes St

130 Van Dam St

238 N Main St

305 Nelson Ave

123 Circle Dr

5 Church St

14 A Kirby Rd

14 Kirby Rd

10 C Kirby 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.

122 South St
Chestertown, NY Local Guide

How much does it cost to rent an apartment in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chestertown Studio Apartments | $1,689 | $1,131 | $2,022 |
| Chestertown 1 Bedroom Apartments | $1,529 | $985 | $2,682 |
| Chestertown 2 Bedroom Apartments | $1,971 | $1,050 | $4,309 |
| Chestertown 3 Bedroom Apartments | $2,315 | $1,225 | $4,263 |
| Chestertown 4 Bedroom Apartments | $2,500 | $2,500 | $2,500 |
Browse Top Apartments in Chestertown
See all Apartments in ChestertownExplore Chestertown
Chestertown, NY Local Guide
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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.
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 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, NY Rentals by Map
See the most popular apartments and homes in Chestertown, NY
Getting Around Chestertown, NY
Walk Score®
15 / 100
Car-Dependent
Almost all errands require a car
Bike Score®
23 / 100
Somewhat Bikeable
Minimal 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 Chestertown
How much are Studio apartments in Chestertown?
There are currently 6 Studio Apartments in Chestertown with rent ranges from $1,131 to $2,022 with an average price of $1,689.
What is the current price range for One Bedroom Chestertown Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Chestertown ranges from $985 to $2,682 with an average monthly rent of $1,529.
What does renting a Two Bedroom Apartment in Chestertown cost?
The monthly rent prices of Two Bedroom Apartments currently available in Chestertown range from $1,050 to $4,309. Today's average rental price for Two Bedrooms here is $1,971.
How expensive are Chestertown Three Bedroom Apartments?
There are currently 18 Three Bedroom Apartments listings available in Chestertown on ApartmentHomeLiving.com. The pricing ranges from $1,225 to $4,263 - averaging $2,315 for the location.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

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.

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.
















