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Apartments for Rent in Chester, NY

All rentals

44 High St #125 - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

Residential Lease, Chester, NY

44 High St #125, Chester, NY 10918

In-unit laundry | Air conditioning | High ceilings

2 beds

2 baths

$2,300

105 Pine Hollow Way - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

105 Pine Hollow Way, Chester, NY 10918

In-unit laundry | Air conditioning | On-site laundry

1 bed

1 bath

$1,750

53 Main St #4 - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

Charming Single Unit on Main St in Chester, NY - Available 09/01 - $2100

53 Main St #4, Chester, NY 10918

In-unit laundry | Assigned parking | Hardwood floor

2 beds

1 bath

$2,100

3 Brookside Ave - Photo 1 of 1

5d+ ago

House for rent in Chester

Residential Lease, Chester, NY

3 Brookside Ave, Chester, NY 10918

In-unit laundry | Business center

3 beds

2.5 baths

$4,200

3102 Whispering Hls #678 - Photo 1 of 1

5d+ ago

Condo for rent in Chester

Residential Lease, Chester, NY

3102 Whispering Hls #678, Chester, NY 10918

In-unit laundry | Furnished | Air conditioning

1 bed

1 bath

$1,600

20 Goshen Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

Residential Lease, Chester, NY

20 Goshen Rd, Chester, NY 10918

In-unit laundry | Garage parking | Hardwood floor

4 beds

2.5 baths

$6,000

2507 Whispering Hls - Photo 1 of 1

5d+ ago

Condo for rent in Chester

Condominium, Condo,Townhouse - Chester, NY

2507 Whispering Hls, Chester, NY 10918

In-unit laundry | Air conditioning | Garage parking

2 beds

1.5 baths

$2,450

12 Lexington Hl #2 - Photo 1 of 1

3d ago

Condo for rent in Harriman

Residential Lease, Harriman, NY

12 Lexington Hl #2, Harriman, NY 10926

In-unit laundry | Assigned parking | Swimming pool

2 beds

2 baths

$2,400

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17 Brookside Rd - Photo 1 of 1

4d ago

House for rent in Monroe

Residential Lease, Monroe, NY

17 Brookside Rd, Monroe, NY 10950

In-unit laundry | Storage | Dishwasher

3 beds

2 baths

$2,850

16 Stage Rd - Photo 1 of 1

5d+ ago

Apartment for rent in Monroe

Residential Lease, Monroe, NY

16 Stage Rd, Monroe, NY 10950

2 beds

1 bath

$1,900

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Find rentals with popular amenities

Assigned Parking

Air Conditioning

In-Unit Laundry

Dishwasher

246 Orchard Dr - Photo 1 of 1

5d+ ago

House for rent in Monroe

Residential Lease, Monroe, NY

246 Orchard Dr, Monroe, NY 10950

Package service

2 beds

1 bath

$2,500

14 Lexington Hl #2 - Photo 1 of 1

5d+ ago

Condo for rent in Harriman

Residential Lease, Harriman, NY

14 Lexington Hl #2, Harriman, NY 10926

In-unit laundry | Assigned parking | Swimming pool

2 beds

2 baths

$2,400

129 Spring St - 127 Spring St. 208 - Photo 1 of 1

5d+ ago

Apartment for rent in Monroe

The Clove at Spring Street LLC - 127 Spring St. 208

129 Spring St - 127 Spring St. 208, Monroe, NY 10950

3 beds

2 baths

$3,200

13 Maple Ln - Photo 1 of 1

5d+ ago

House for rent in Monroe

Top floor for rent

13 Maple Ln, Monroe, NY 10950

In-unit laundry | On-site laundry | Balcony

3 beds

1 bath

$3,000

57 Wedgewood Dr - Photo 1 of 1

5d+ ago

House for rent in Goshen

Residential Lease, Goshen, NY

57 Wedgewood Dr, Goshen, NY 10924

In-unit laundry | On-site laundry | Hardwood floor

4 beds

2 baths

$3,600

1 Pinehurst Cir - Photo 1 of 1

5d+ ago

Townhouse for rent in Monroe

Residential Lease, Monroe, NY

1 Pinehurst Cir, Monroe, NY 10950

In-unit laundry | Garage parking | Swimming pool

3 beds

3.5 baths

$4,600

Find sweet deals near Chester

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$2,100

Chester

$1,900

Monroe

$1,600

Monroe

$3,600

Goshen

320 High St - Photo 1 of 1

5d+ ago

House for rent in Monroe

nice house on a flat property

320 High St, Monroe, NY 10950

Hardwood floor | Fireplace | Dishwasher

3 beds

1 bath

$2,800

12 Lexington Hl #7 - Photo 1 of 1

5d+ ago

Condo for rent in Harriman

Residential Lease, Harriman, NY

12 Lexington Hl #7, Harriman, NY 10926

In-unit laundry | On-site laundry | Swimming pool

2 beds

2 baths

$2,575

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Listings within 10 miles
7 Parkway #2 - Photo 1 of 1

5d+ ago

Apartment for rent in Goshen

Residential Lease, Goshen, NY

7 Parkway #2, Goshen, NY 10924

In-unit laundry | Hardwood floor | Ceiling fan

2 beds

1 bath

$2,850

76 Spring St #NA - Photo 1 of 1

5d+ ago

Apartment for rent in Goshen

$1,750 - 1 Bedroom 1 Bathroom House In Goshen With Great Amenities

76 Spring St #NA, Goshen, NY 10924

Assigned parking | Ceiling fan | Carpet

1 bed

1 bath

$1,750

260 W Main St #11 - Photo 1 of 1

5d+ ago

Apartment for rent in Goshen

Residential Lease, Goshen, NY

260 W Main St #11, Goshen, NY 10924

In-unit laundry | Air conditioning | Assigned parking

2 beds

2 baths

$3,195

42 Underhill Trl - Photo 1 of 1

5d+ ago

House for rent in Monroe

Residential Lease, Monroe, NY

42 Underhill Trl, Monroe, NY 10950

Hardwood floor | Ceiling fan | Storage

1 bed

1 bath

$1,600

73 Webster Ave #A - Photo 1 of 1

5d+ ago

Apartment for rent in Goshen

Residential Lease, Goshen, NY

73 Webster Ave #A, Goshen, NY 10924

Dishwasher

1 bed

1 bath

$1,650

131 Conklin Rd - Photo 1 of 1

5d+ ago

House for rent in Monroe

Residential Lease, Monroe, NY

131 Conklin Rd, Monroe, NY 10950

In-unit laundry | On-site laundry | Storage

2 beds

5 baths

$2,450

112 Green St #2 - Photo 1 of 1

5d+ ago

Apartment for rent in Goshen

Residential Lease, Goshen, NY

112 Green St #2, Goshen, NY 10924

Hardwood floor

1 bed

1 bath

$1,850

Showing 1 - 25 of 25 results
Home > Apartments in Chester
Updated: September 16, 2026

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Chester, NY apartments for rent

Renting in Chester, NY at a glance

As of today, Chester's median rent price is $2,350 per month.

Median rent

$2,350

Rentals, last 30 days

20

Rent by unit type
SizeValueYoY
All bedrooms$2,350N/A
1 bedroom$2,100N/A
2 bedroom$2,400N/A
Not sure what you can afford? Try our rent calculator

Local insights: What it's like to live in Chester, NY

Chester, NY, is appreciated for its scenic views and access to outdoor activities like hiking and fishing, making it a desirable spot for nature enthusiasts. Residents often mention the friendly atmosphere and the quiet, laid-back lifestyle that comes with living in a small town. While many enjoy the slower pace, some express concerns about limited shopping and dining options, which can make day-to-day life a bit inconvenient for renters. Overall, locals find it a pleasant place to live, particularly for those who value tranquility and natural surroundings.

Frequently asked questions

Are utilities usually included in rent in Chester, NY?

Based on our current listings, utilities-included rentals are extremely rare in Chester, appearing in under 1% of units. One-bedrooms show the highest rate at just 0.09% of listings.

Are most apartments in Chester, NY largely older buildings or new developments?

Based on Zumper's listings data, Chester's rental market is dominated by ranch-style homes, which make up 34.2% of all properties. These single-story homes with open floor plans and horizontal lines became popular in post-World War II America, reflecting the area's mid-20th century suburban development.

Methodology: How we got this data

Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.

Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.

Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.

Looking for apartments in Chester, NY near you?

Chester, NY rental availability
🔑Available apartment rentals25
💰Best rent deal3102 Whispering Hls #678
✨Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos