
Homes for Rent near Chestertown, NY (42 Rentals)


575 N Broadway

52 Trottingham Rd

5 Loughberry Rd

11 Keyes St

4259 NY-50

2484 VT-30

3 Colonial Court
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

209 N Greenfield Rd

234 Colebrook Rd

8 Geer Rd

24 Elizabeth Ln

66 Warren St

75 Coolidge Hill Rd

13 Pheasant Walk

182 Excelsior Ave
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.

79 Locust Grove Rd

101 King Rd

48 Smith Bridge Rd

29 Quail Ct

4264 NY-50

569 N Broadway

7 James Ct

13 Old Deer Camp Rd
Neighborhood & Market Insights: How to Choose the Right Area to Rent
Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

80 Murray Hill S Rd

33 Chuckwagon Trail

155 Dorr Dr

7 N Circular St

157 Louden Rd

3 Ashleigh Ln

12 Seneca Dr

57 Taconic 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.

238 N Main St

83 Prospect Ave

20.5 Lexington Ave

260 Clark Rd

16 Newton St

3320 Travis Point Way

134 Pickle Hill Rd

7457 NY-8
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.

32 Gooseneck Rd

32 Flat Rock Rd
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 | $6,086 | $1,950 | $10,000+ |
| Chestertown 3 Bedroom Homes for Rent | $2,919 | $1,450 | $6,000 |
| Chestertown 4 Bedroom Homes for Rent | $6,709 | $2,800 | $10,000+ |
| Chestertown 5 Bedroom Homes for Rent | $4,166 | $3,000 | $6,000 |
| Chestertown 6 Bedroom Homes for Rent | $23,000 | $3,000 | $10,000+ |
Browse Top Homes for Rent in Chestertown
Explore Chestertown
Chestertown, NY Local Guide
- Nearby Cities
- ZIP codes
- Local Counties
A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.
Read Article18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.
Read ArticleNavigating 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.
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 New York 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, NY Rentals by Map
See the most popular apartments and homes in Chestertown, NY
Frequently Asked Questions about Chestertown
What type of rentals are currently available in Chestertown?
There are currently 67 Apartments for Rent in Chestertown, NY with pricing that ranges from $869 to $5,139. There are also 42 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $850 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 $850 to $40,000 with an average monthly rent of $4,237.
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 $1,275 to $5,139, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,450 to $6,000. Four Bedroom Single-Family rentals are also available starting from $2,800 and Four Bedroom Apartments start at $2,550.
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

How Commercial-to-Residential Property Conversions Help the Housing Crisis
Written by: Robin Stewart
Many housing markets throughout America share a common complaint: a lack of affordable rental properties.

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.