
Apartments for Rent in Chestertown, NY (109 Rentals) Page 2 of 3


32 Flat Rock Rd

16 Newton St

21 Hall Rd

1809 Ridge Rd

134 Pickle Hill Rd

12 Seneca Dr

33 Chuckwagon Trail

38 Henry St

93 Curtis Ln

189 Blissville Rd

139 Traver Rd

7 James Ct

260 Clark Rd

57 Goose Hollow Rd

29 Quail Ct

157 Louden Rd

4264 NY-50

182 Excelsior Ave

48 Smith Bridge Rd

79 Locust Grove Rd

101 King Rd

13 Old Deer Camp Rd

569 N Broadway

3 Ashleigh Ln

7 N Circular St

116 Catherine St

18 Granite St

106 Greenfield Ave

155 Dorr Dr

16-18 Division St

80 Murray Hill S Rd

57 Taconic Rd

20.5 Lexington Ave

238 N Main St

83 Prospect Ave

38 West St

45 State Route 9P

6317-6321 State Route 9

Panther Mountain Senior

Schermerhorn - Queensbury

80 Main St

18 Luzerne Rd

20 Grove Ave

Schermerhorn - Hudson Falls Deer Run

Reserve at Saratoga Springs

464 Maple Ave

Williamsburg Court

14 Bowman St

Oakhaven Acres
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 | $1,908 | $1,081 | $2,506 |
| Chestertown 1 Bedroom Apartments | $1,807 | $869 | $3,166 |
| Chestertown 2 Bedroom Apartments | $2,274 | $1,050 | $4,699 |
| Chestertown 3 Bedroom Apartments | $2,672 | $1,275 | $5,139 |
| Chestertown 4 Bedroom Apartments | $2,603 | $2,550 | $2,656 |
How much does it cost to rent a home in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| 2 Bedroom Homes | $7,756 | $1,850 | $10,000+ |
| 3 Bedroom Homes | $4,330 | $1,300 | $10,000+ |
| 4 Bedroom Homes | $11,110 | $3,000 | $10,000+ |
| 5 Bedroom Homes | $3,250 | $3,000 | $3,500 |
| 6 Bedroom Homes | $33,000 | $10,000 | $10,000+ |
Browse Top Apartments in Chestertown
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Frequently Asked Questions about Chestertown
What is the current pricing and availability for apartments for rent in Chestertown, NY?
As of today, August 29, 2026, there are currently 109 available Chestertown apartments priced from $869 to $5,139, with an average monthly rent of $2,118.
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 $869 to $3,166 with an average monthly rent of $1,807.
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 $4,699. Today's average rental price for Two Bedrooms here is $2,274.
How expensive are Chestertown Three Bedroom Apartments?
There are currently 19 Three Bedroom Apartments listings available in Chestertown on ApartmentHomeLiving.com. The pricing ranges from $1,275 to $5,139 - averaging $2,672 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

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.

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.