
Homes for Rent in Chestertown, NY (36 Rentals)


29 Sunrise Ln

11 Keyes St

209 Ottawa St

11208 NY-22

108 Birdsall Rd

12 Seneca Dr

8 Carefree Ln

4819 NY-50
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.

4817 NY-50

40 Tom Sawyer Dr

31 Safford Rd

48 Atwell Rd

9 Muskett Dr

96 Walworth St

305 Nelson Ave

17 Granite St
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.

130 Van Dam St

30 Whistler Ct

30 Excelsior Spring Ave

101 Union Ave

77 Van Dam St

108 High Rock Ave

34 Ruggles Rd

275 Louden Rd

16 Claire Pass

148 Edie Rd
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.

117 Circular St

6 Pearl St

161 Excelsior Ave

22 Kendrick Hill Rd

305 Circular St

1 Cider Mill Way

30 Patricia Ln

31 East St

1487 County Hwy 110
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.
Chestertown, NY Local Guide

How much does it cost to rent a home in Chestertown?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Chestertown 2 Bedroom Homes for Rent | $5,227 | $1,845 | $10,000+ |
Chestertown 3 Bedroom Homes for Rent | $5,549 | $1,900 | $10,000+ |
Chestertown 4 Bedroom Homes for Rent | $3,858 | $2,650 | $7,500 |
Browse Top Homes for Rent in Chestertown
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Chestertown, NY Local Guide
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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.
Remember the 3 Rules of Real Estate:Location, Location, Location!
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Frequently Asked Questions about Chestertown
What type of rentals are currently available in Chestertown?
There are currently 46 Apartments for Rent in Chestertown, NY with pricing that ranges from $995 to $4,659. There are also 36 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $1,350 to $40,000.
What is the current price range for Rental Homes in Chestertown?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestertown ranges from $1,350 to $40,000 with an average monthly rent of $4,118.
How much are larger Three and Four Bedroom Rentals in Chestertown?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestertown range from $1,225 to $4,607, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,900 to $40,000. Four Bedroom Single-Family rentals are also available starting from $2,650 and Four Bedroom Apartments start at $2,500.
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.

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.

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.