Cheap Apartments for Rent in Chestertown, NY from $900 (37 Rentals)

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Search the lowest-cost Apartments available for rent right now in Chestertown.

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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The Residences at 628 Maple
$1,395 - $2,100
Total Monthly Price

Total Monthly Price

Base Rent
$1,395 - $2,100
Total Monthly Price
$1,395 - $2,100
1 to 2 Bedroom Apartments Contact Us For Availability

The Residences at 628 Maple

628 Maple AveSaratoga Springs, NY 12866
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14 Bowman St
Rent Specials
$1,500
Total Monthly Price

Total Monthly Price

Base Rent
$1,500
Total Monthly Price
$1,500
1 Bedroom Apartments Available Now

14 Bowman St

14 Bowman StSaratoga Springs, NY 12866
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McGregor Village
Rent Specials
$1,575
Total Monthly Price

Total Monthly Price

Base Rent
$1,515
Required Monthly Fees
$60
Total Monthly Price
$1,575
2 Bedroom Apartments Available Now

McGregor Village

1 Mountain Ledge DrWilton, NY 12831
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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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Schermerhorn - Queensbury
1 to 2 Bedroom Apartments

Schermerhorn - Queensbury

44 Willowbrook RdQueensbury, NY 12804
Corporate Housing
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13 Church St
1 Bedroom Apartments

13 Church St

13 Church StRutland, VT 05701
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20 Grove Ave
Studio to 2 Bedroom Apartments

20 Grove Ave

20 Grove AveGlens Falls, NY 12801
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80 Main St
1 to 2 Bedroom Apartments

80 Main St

80 Main StQueensbury, NY 12804
  • Utilities Included

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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district425
Studio to 3 Bedroom Apartments

district425

425 Glen StGlens Falls, NY 12801
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38 West
2 Bedroom Apartments

38 West

38 West StFair Haven, VT 05743
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Otterside Apartments
1 to 2 Bedroom Apartments

Otterside Apartments

39 Otterside Ct NMiddlebury, VT 05753
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23 Washington St
Studio to 1 Bedroom Apartments

23 Washington St

23 Washington StRutland, VT 05701
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246 West Ave
1 to 2 Bedroom Apartments

246 West Ave

246 West AveSaratoga Springs, NY 12866
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45 State Route 9P
2 Bedroom Apartments

45 State Route 9P

45 New York 9PBallston Spa, NY 12020
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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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Showing Results 1-37, Page 1 of 1

Chestertown, NY Local Guide

Cheapest Available Chestertown Apartments for Rent and Nearby

 

The cheapest available apartment rental in Chestertown, NY is a 2 Beds unit found at 25 LaRose priced from $1,034. The Landings at Kingsbury has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,050. Here is today’s list of the most affordable Chestertown apartments for rent:

Apartment ListingModel NameBed/BathPriced From
25 LaRose2BR2BR,1BA$1,034
The Landings at KingsburyB11BR,1BA$1,050
Reserve at Saratoga SpringsB22BR,1BA$1,099
Whispering Pines1 Bedroom (Section B)1BR,1BA$1,110
Glen Street AssociatesStudioStudio,1BA$1,125
Sherwood Terrace ApartmentsStudioStudio,1BA$1,136
13 Church St1 bedroom1BR,1BA$1,275
Schermerhorn - South Glens FallsTownhome Two Bedroom One Bath2BR,1BA$1,410
Williamsburg Court2 BEDROOM2BR,1BA$1,450
35-53-79 Meadow Ln2 br / 1 ba2BR,1BA$1,450

Best Value Apartments for Rent in Chestertown, NY and Nearby

As of February 21, 2026 the best value apartment in the Chestertown area is the $1.42 price per square foot Phase 2 Model at English Village Apartments in the starting from $1,748. The second greatest value Chestertown apartment is the 2BD/2BA - (W) Model at Park Place at Wilton, LLC starting at $2,100 with a $1.81 price per square foot . Here is today’s list of the best values for Chestertown apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
English Village ApartmentsPhase 22BR,1BA$1.42
Park Place at Wilton, LLC2BD/2BA - (W)2BR,2BA$1.81
Oakhaven AcresBuilding 52BR,1BA$1.60
McGregor Village2 Beds/1 Bath + Balcony & W/D2BR,1BA$1.64
Williamsburg Court2 BEDROOM2BR,1BA$1.53
The Landings at KingsburyB1BR,1BA$1.15
Schermerhorn - South Glens FallsTownhome Two Bedroom One Bath2BR,1BA$1.57
35-53-79 Meadow Ln2 br / 1 ba2BR,1BA$1.71
25 LaRose2BR2BR,1BA$1.22
Reserve at Saratoga SpringsA11BR,1BA$1.70

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

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

Pet Friendliness Lifestyle Score

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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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Frequently Asked Questions about Cheap Chestertown Apartments

What is the Cheapest Studio apartment in Chestertown?

Currently the most affordable Cheap Studio Apartment in Chestertown is at Glen Street Associates listed at $1,125.

How much is rent for a Cheap One Bedroom Chestertown Apartment?

The lowest price for a Cheap One Bedroom Chestertown Apartment is $1,050 at The Landings at Kingsbury.

What is the lowest price for a Cheap Two Bedroom Chestertown Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Chestertown is starting from $1,034 at 25 LaRose.

What is the most affordable Chestertown Three Bedroom Apartment?

The best deal on a cheap Chestertown Three Bedroom Apartment rental is at Reserve at Saratoga Springs and starts from $1,669.

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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Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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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.