Apartments for Rent in Chestertown, NY Under $2,000 (59 Rentals)

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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.

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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.

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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.

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property at 130 Van Dam St

$1,895

2 Bedroom Rentals

Available Now

130 Van Dam St

Saratoga SpringsNY12866
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45 State Route 9P
2 Bedroom Apartments

45 State Route 9P

45 New York 9PBallston Spa, NY 12020
  • Utilities Included
  • Smoke Free
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38 West
2 Bedroom Apartments

38 West

38 West StFair Haven, VT 05743
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Chestertown, NY Local Guide

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.

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The 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.

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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.

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Quick 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.

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Pet Friendly Lifestyle

Ranked #

Among cities in New York for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

Pet Friendly

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chestertown, NY Rentals by Map

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See the most popular apartments and homes in Chestertown, NY

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Chestertown, NY Apartments Map
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Chestertown, NY Rental Homes Map

Frequently Asked Questions about Chestertown

How much are Studio apartments in Chestertown?

There are currently 10 Studio Apartments in Chestertown with rent ranges from $816 to $2,234 with an average price of $1,807.

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 $3,055 with an average monthly rent of $1,792.

What does renting a Two Bedroom Apartment in Chestertown cost?

The monthly rent prices of Two Bedroom Apartments currently available in Chestertown range from $1,034 to $4,704. Today's average rental price for Two Bedrooms here is $2,209.

How expensive are Chestertown Three Bedroom Apartments?

There are currently 20 Three Bedroom Apartments listings available in Chestertown on ApartmentHomeLiving.com. The pricing ranges from $1,225 to $4,542 - averaging $2,548 for the location.

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

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How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips

Written by: Justin Habersaat

Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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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.

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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.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!