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Apartments for Rent in Chester, NY

Average rent

$2,925
increased by55%

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45 Conklingtown Rd - Photo 1 of 1

1d ago

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45 Conklingtown Rd, Chester, NY 10918

In-unit laundry | Furnished | Air conditioning

7 beds

6 baths

$18,879

Apartment for rent

Furnished 7-bed retreat with private pool

Set in Chester, NY, this pet-friendly 7-bed, 6-bath apartment offers a fully furnished retreat with a private summer pool and spacious outdoor living areas. The state-of-the-art kitchen features granite countertops, a 6-burner gas stove, and Nespresso machine, while amenities include a gas fireplace, pool table, and dedicated workspace areas with high-speed internet.

5 Laroc Rd - Photo 1 of 1

2d ago

House for rent in Chester

Spacious 6BR/2BA Single Family Home in Chester, NY

5 Laroc Rd, Chester, NY 10918

Air conditioning | Garage parking | Storage

6 beds

2 baths

$4,000

House for rent

Available Mar 27

Spacious Home with Massive Yard and Ample Storage

This stunning 6-bedroom, 2-bath home offers a massive backyard perfect for outdoor entertaining and enjoyable gatherings on the spacious deck. With central air conditioning and heating for year-round comfort, the interior boasts huge living spaces ideal for relaxation. The property also includes a garage for secure parking and two sheds for all your storage needs. Don't miss this incredible opportunity for comfortable living!

1502 Whispering Hls - Photo 1 of 1

5d+ ago

Condo for rent in Chester

CONDOS - Chester, NY

1502 Whispering Hls, Chester, NY 10918

In-unit laundry | Garage parking | Swimming pool

3 beds

2 baths

$2,900

Condo for rent

3-bed condo with pool, gym, and tennis courts

Quietly set in Chester, NY, this updated 3-bed, 2-bath condo features vaulted ceilings, a fireplace, and fresh paint throughout. The 1,316 sqft layout includes in-unit laundry, central air, and attached garage parking. Resort-style amenities include pools, tennis courts, fitness center, clubhouse, and playgrounds, with easy highway access for commuting.

168 Pine Hill Rd #1 - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

APARTMENT - Other - Chester, NY

168 Pine Hill Rd #1, Chester, NY 10918

In-unit laundry | Assigned parking | Hardwood floor

3 beds

1.5 baths

$2,900

Apartment for rent

3-bed Chester apartment with utilities included

A apartment in Chester, NY, this 3-bed, 1.5-bath two-level unit includes utilities, heat, and hot water in the rent. The 1,600 sqft layout features an eat-in kitchen with stainless appliances, in-unit laundry, hardwood floors, and central air. A private deck and patio add outdoor space, with assigned parking steps from the door and lawn care covered by the landlord.

1403 Kings Hwy - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

MULTI_FAMILY - Other - Chester, NY

1403 Kings Hwy, Chester, NY 10918

In-unit laundry | Hardwood floor | Fireplace

3 beds

2.5 baths

$3,900

$3,750

Price drop

Apartment for rent

3-bed farmhouse with mountain views & pizza oven

Set in Chester, NY, this 3-bed, 2.5-bath farmhouse apartment offers 3,200 sqft of luxury living with soaring 18-foot ceilings and authentic barn beams. The gourmet kitchen features a commercial-grade range, granite counters, and imported brick pizza oven, while the great room showcases a floor-to-ceiling fireplace and wide-plank hardwood floors throughout.

28 Academy Ave #2 - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

MULTI_FAMILY - Colonial - Chester, NY

28 Academy Ave #2, Chester, NY 10918

Storage

3 beds

1 bath

$2,695

Apartment for rent

Spacious 3-bed colonial apartment with attic

This 3-bed, 1-bath apartment in Chester features a finished attic that works as a home office or extra living space. The 2,386 sqft colonial-style unit includes storage and baseboard heating across six rooms on the second floor. Close to shopping, restaurants, parks, schools, and major commuter routes in the Village of Chester.

2722 Whispering Hls - Photo 1 of 1

5d+ ago

Condo for rent in Chester

CONDOS - Chester, NY

2722 Whispering Hls, Chester, NY 10918

In-unit laundry | Garage parking | Swimming pool

3 beds

2.5 baths

$2,950

Condo for rent

Updated 3-bed end unit condo with 2-car garage

Located in Chester, NY, this fully refreshed 3-bed, 2.5-bath end unit condo features new designer paint, luxury vinyl plank flooring, and stainless steel appliances throughout its 1,331 sqft layout. The two-car garage with new doors adds convenience, while community amenities include a clubhouse with gym, tennis and basketball courts, playgrounds, and two pools.

1208 Whispering Hls - Photo 1 of 1

5d+ ago

Condo for rent in Chester

CONDOS - Chester, NY

1208 Whispering Hls, Chester, NY 10918

In-unit laundry | Garage parking | On-site laundry

2 beds

1.5 baths

$2,490

Condo for rent

2-bed condo with garage and pool access

Set in Chester, NY, this 2-bed, 1.5-bath condo offers 1,053 sqft with a 1-car garage and central air. The updated kitchen pairs with laminate flooring downstairs and in-unit laundry. Upstairs features a primary suite with vaulted ceilings, walk-in closet, and skylight. Pool access and guest parking add convenience for this commuter-friendly location.

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66 Murray Dr - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Ranch - Chester, NY

66 Murray Dr, Chester, NY 10918

In-unit laundry | Furnished | Hardwood floor

4 beds

2 baths

$5,300

House for rent

Furnished 4-bed ranch with mountain views & hot tub

Set in Chester, NY, this fully furnished ranch-style house offers 4-bed, 2-bath living on 1.2 acres with Hudson Valley mountain views. The 3,412 sqft layout features a chef's kitchen with double ovens, open living areas with fireplace, and a primary suite with sunroom access. A hot tub, fire pit, and oversized deck create an outdoor retreat just one hour from NYC.

20 Goshen Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Colonial - Chester, NY

20 Goshen Rd, Chester, NY 10918

In-unit laundry | Garage parking | Hardwood floor

4 beds

2.5 baths

$6,000

House for rent

Colonial 4-bed estate with horse trails & orchard

Quietly set in Chester, NY, this colonial-style 4-bed, 2.5-bath house spans 3,348 sqft on expansive grounds with private horse trails and a mature fruit orchard. The custom home features hardwood floors, high ceilings, central air, and a 3-car garage with 10-foot doors. An outdoor wood-burning furnace adds cost savings, while the brick exterior and 14 rooms provide ample space for those seeking a self-sufficient lifestyle with modern amenities.

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Garage Parking

Dishwasher

In-Unit Laundry

204 Pine Hollow Way - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

1 bed

1 bath

$1,750

Apartment for rent

1-bed Chester apartment with private patio

Set in Chester, NY, this 1-bed, 1-bath apartment offers 1,000 sqft of open-concept living with abundant natural light and a private patio. The unit includes a large bedroom with ample closet space, private laundry hookups, and sits just 60 minutes from NYC via express bus. Close to Hudson Valley wineries, apple picking, and shopping with easy access to rail transit and major highways.

82 High St #5 - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

APARTMENT - Contemporary, Modern - Chester, NY

82 High St #5, Chester, NY 10918

In-unit laundry | Air conditioning | Carpet

2 beds

1 bath

$2,200

Apartment for rent

Bright 2-bed penthouse with deck and parking

Set in Chester, NY, this top-floor 2-bed, 1-bath penthouse apartment offers an open layout with plenty of natural light and an outside deck. The 900 sqft modern unit features an updated kitchen with stainless steel appliances, in-unit washer and dryer, central air, and large double closets in the primary bedroom. Water included in rent, plus 2 parking spaces and easy access to Route 17.

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

Condo for rent

Available Aug 1

2-bed condo with garage and community pool

This 2-bed, 1.5-bath condo in Chester features a cozy fireplace, in-unit laundry, and second-floor skylight across 1,086 sqft. The unit includes a 2-car garage and private fenced patio, plus community amenities like a swimming pool, tennis court, and playground. Close to hiking and biking trails with top-rated schools nearby.

283 Prospect Rd - Photo 1 of 1

1d ago

Our team has verified this company

Verified

283 Prospect Rd, Monroe, NY 10950

In-unit laundry | Furnished | Air conditioning

7 beds

4 baths

$27,997

Apartment for rent

4370 Route 94 - Photo 1 of 1

4h ago

House for rent in Goshen

In-unit laundry | Garage parking | On-site laundry

3 beds

3 baths

$3,500

House for rent

101 Tondo Cir - Photo 1 of 1

2d ago

Apartment for rent in Harriman

APARTMENT - Harriman, NY

101 Tondo Cir, Harriman, NY 10926

In-unit laundry | Air conditioning | Hardwood floor

2 beds

2 baths

$2,450

Apartment for rent

Find sweet deals near Chester

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

120 Orchard St - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Cape Cod - Monroe, NY

120 Orchard St, Monroe, NY 10950

In-unit laundry | Garage parking | Hardwood floor

2 beds

1 bath

$3,000

House for rent

18 Lexington Hl #12 - Photo 1 of 1

5d+ ago

Condo for rent in Harriman

CONDOS - Other - Harriman, NY

18 Lexington Hl #12, Harriman, NY 10926

In-unit laundry | Balcony | Swimming pool

2 beds

2 baths

$2,600

Condo for rent

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129 Spring St - 127 Spring St. 201 - Photo 1 of 1

5d+ ago

Apartment for rent in Monroe

The Clove at Spring Street LLC - 127 Spring St. 201

129 Spring St - 127 Spring St. 201, Monroe, NY 10950

3 beds

2 baths

$3,200

Apartment for rent

Available Aug 25

11 Peterson Rd - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Colonial - Monroe, NY

11 Peterson Rd, Monroe, NY 10950

Garage parking | Hardwood floor | Walk-in closets

4 beds

2.5 baths

$4,000

House for rent

108 Circle Dr - Photo 1 of 1

5d+ ago

House for rent in Monroe

108 Circle Dr, Monroe, NY 10950

Furnished | Air conditioning | Garage parking

5 beds

0 baths

$5,500

House for rent

Listings within 10 miles
11 Webster Ave #7 - Photo 1 of 1

3h ago

Apartment for rent in Goshen

Large Studio Apartment with Village Views - ALL Utilities Included

11 Webster Ave #7, Goshen, NY 10924

Carpet | Outdoor space

1 bed

1 bath

$1,800

Apartment for rent

Available Jun 17

155 Main St #6 - Photo 1 of 1

2d ago

Apartment for rent in Goshen

APARTMENT - Colonial - Goshen, NY

155 Main St #6, Goshen, NY 10924

1 bed

1 bath

$1,750

Apartment for rent

24 Ford Ct #A1 - Photo 1 of 1

5d+ ago

Townhouse for rent in Monroe

CONDOS - Monroe, NY

24 Ford Ct #A1, Monroe, NY 10950

In-unit laundry | Swimming pool | Walk-in closets

3 beds

2.5 baths

$3,800

House for rent

9 Emerald Trl - Photo 1 of 1

5d+ ago

House for rent in Monroe

3-Bed, 1-Bath Renovated Home for Rent - Move-In Ready!

9 Emerald Trl, Monroe, NY 10950

In-unit laundry | Hardwood floor | Dishwasher

3 beds

1 bath

$2,350

House for rent

Available Jul 1

Showing 1 - 25 of 25 results
Home > Apartments in Chester
Updated: June 18, 2026

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Learn more about renting in Chester, NY

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.

Are utilities usually included in rent in Chester, NY?

Chester rental properties rarely include utilities as part of the rent package. Less than 1% of total listings include utilities in their monthly rent, with only occasional 1-bedroom and 3-bedroom units offering this arrangement.

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

Chester's rental market features primarily older architectural styles from the mid-20th century. Ranch-style homes dominate at 35% of properties, reflecting the post-World War II suburban development era of the 1950s and 1960s. Contemporary architecture represents 27% of the market, also emerging from the mid-20th century period.

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?

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💰Best rent deal204 Pine Hollow Way
Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
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