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Apartments for Rent in Chester, NY

Average rent

$2,200
increased by9%

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35 Glenmere Rd Apt A #Apt A - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

APARTMENT - Chester, NY

35 Glenmere Rd Apt A #Apt A, Chester, NY 10918

In-unit laundry | Outdoor space

2 beds

1 bath

$2,100

Apartment for rent

Bright & Spacious Apartment with Modern Updates

Experience comfort in this freshly painted 2-bedroom apartment featuring new flooring and a generous living room. The eat-in kitchen includes newer appliances, and in-unit laundry enhances convenience. Enjoy the charm of Chester while being close to shops and restaurants. Plus, with included lawn care and snow removal, this cozy home ensures a hassle-free lifestyle. Perfect for those seeking both space and modern amenities in a lovely setting.

1818 Whispering Hls - Photo 1 of 1

5d+ ago

Condo for rent in Chester

CONDOS - Contemporary - Chester, NY

1818 Whispering Hls, Chester, NY 10918

In-unit laundry | Garage parking | Walk-in closets

2 beds

1 bath

$2,400

Condo for rent

Spacious Townhouse with Modern Upgrades & Garage

This contemporary townhouse features 2 bedrooms and 1.5 bathrooms across 1,086 sq ft of bright living space. Enjoy a private 2-car garage, convenient in-unit laundry, and modern updates like new LVP flooring. The layout includes a cozy living room with a fireplace, an airy dining area, and a well-equipped kitchen. The bedrooms offer walk-in closets, while the private patio adds outdoor enjoyment. Ideally located near local amenities and major highways, making it perfect for commuters.

118 Booth Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Contemporary - Chester, NY

118 Booth Rd, Chester, NY 10918

Swimming pool | Walk-in closets | Storage

4 beds

3 baths

$3,800

House for rent

Elegant Bi-Level Home on 3+ Serene Acres

This stunning 4-bedroom, 3-bath bi-level home offers over 2,457 sq. ft. of living space on a picturesque 3+ acre lot. Enjoy a stylish European kitchen with quartz countertops and marbled baths. The inviting open layout features high-end ceramics and restored oak floors, while the expansive outdoor space is perfect for a pool or tranquil sanctuary. With new mechanicals, windows, and roof, this exquisite property is ready to move in and enjoy a peaceful escape from the daily hustle.

82 High St Apt 5 #5 - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

APARTMENT - Contemporary, Modern - Chester, NY

82 High St Apt 5 #5, Chester, NY 10918

In-unit laundry | Air conditioning | Carpet

2 beds

1 bath

$2,200

Apartment for rent

Bright Penthouse with Open Layout & Deck

Experience vibrant living in this spacious top-floor penthouse featuring an open layout and abundant natural light. The updated kitchen boasts a new stainless steel refrigerator and dishwasher. The primary bedroom offers large double closets and accommodates a king-size bed. Enjoy a sun-filled living/dining area with access to an outside deck, plus the convenience of in-unit laundry. Central air and an oversized bathroom enhance comfort in this modern 900 sq. ft. apartment.

948 Craigville Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

948 Craigville Rd, Chester, NY 10918

Air conditioning | Hardwood floor | Fireplace

3 beds

3 baths

$4,250

House for rent

Charming 1850s Renovated Home on 11 Acres

Experience serene country living in this beautifully renovated 1850s home set on over 11 acres. With 2,840 sq ft of space, this property features radiant heated floors, central A/C, and a stand-by generator. The lush, fenced-in pasture includes run-in sheds, perfect for horses. This home offers three bedrooms, two offices, and a loft, making it ideal for those who seek tranquility and outdoor activities. Conveniently located near shopping, dining, and attractions, it’s a perfect blend of comfort and nature.

2507 Whispering Hls - Photo 1 of 1

5d+ ago

House for rent in Chester

Single Family Residence, Traditional - Chester, NY

2507 Whispering Hls, Chester, NY 10918

In-unit laundry | Garage parking | Swimming pool

2 beds

1 bath

$2,300

House for rent

Modern 2-Bed Retreat with Pool & Tennis Court

Experience comfort in this cozy 2-bedroom, 1.5-bath home featuring a welcoming fireplace and skylight. Enjoy modern conveniences with a new furnace and refrigerator, in-unit laundry, and a private fenced patio. Additional perks include a refreshing swimming pool, children's playground, and nearby hiking trails. With a 2-car garage and convenient access to outdoor activities, this rental offers an ideal lifestyle for relaxation and fun in the great outdoors.

8 Main St - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

Apartment - Chester, NY

8 Main St, Chester, NY 10918

High ceilings

1 bed

1 bath

$1,700

Apartment for rent

Bright Apartment with Unique Exposed Brick Charm

This spacious one-bedroom apartment features an inviting open floor plan on the 3rd floor, highlighted by stunning exposed brick walls that create a warm, rustic atmosphere. With plenty of natural light and a view of the mountains, this 700 sq ft unit combines comfort and character. Conveniently located near all amenities and Route 17, it provides easy access for a vibrant lifestyle in the Village of Chester. Enjoy high ceilings and a cozy ambiance in this charming space.

82 High St #2 - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

Apartment, Contemporary,Garden,Traditional - Chester, NY

82 High St #2, Chester, NY 10918

In-unit laundry | Air conditioning | Carpet

2 beds

1 bath

$2,200

Apartment for rent

Bright First-Floor Apartment with Spacious Living

This sun-filled ground-floor apartment features 2 bedrooms, including a primary suite with double closets, perfect for a king-sized bed. Enjoy an updated kitchen with stainless steel appliances and a cozy patio overlooking a wooded area. Comfort is assured with central air and in-unit laundry. Conveniently located near Rt 17 and shopping, this charming contemporary space offers everything you need for comfortable living in a pleasant setting.

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7 Greycourt Ave #6 - Photo 1 of 1
New construction

5d+ ago

Apartment for rent in Chester

Apartment - Chester, NY

7 Greycourt Ave #6, Chester, NY 10918

In-unit laundry | High ceilings | Business center

1 bed

1 bath

$2,100

Apartment for rent

Modern & Bright 1-Bedroom Apartment Awaits!

Experience the charm of Chester in this brand new 1-bedroom, 1-bathroom apartment. Spanning 675 sq ft, it features elegant vinyl plank flooring and a stunning kitchen with stainless steel appliances and quartz countertops. Enjoy abundant natural light, a full-size washer and dryer, and off-street parking. Perfectly located, this immaculate space is just a stroll away from local shops and restaurants, with easy access to parks and commuting options.

7 Greycourt Ave #5 - Photo 1 of 1
New construction

5d+ ago

Apartment for rent in Chester

Apartment - Chester, NY

7 Greycourt Ave #5, Chester, NY 10918

In-unit laundry | High ceilings | Business center

1 bed

1 bath

$2,200

Apartment for rent

Bright New 1-Bedroom Apartment in Chester!

This stunning 1-bedroom, 1-bath apartment features fresh modern finishes and vinyl plank flooring throughout. Enjoy a stylish kitchen with stainless steel appliances and quartz countertops. Natural light fills the space, complemented by a full-size washer and dryer for convenience. With off-street parking and a prime location near shops, restaurants, and parks, this immaculate, move-in-ready home is perfect for a vibrant lifestyle.

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Dishwasher

Air Conditioning

In-Unit Laundry

High Ceilings

3917 Whispering Hls - Photo 1 of 1

5d+ ago

Condo for rent in Chester

CONDOS - Chester, NY

3917 Whispering Hls, Chester, NY 10918

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

2 beds

1 bath

$2,400

Condo for rent

Charming Two-Level Condo with Modern Amenities

This beautifully maintained two-level condo features a galley kitchen with stainless steel appliances and in-unit laundry. Enjoy cozy evenings by the fireplace or relax on your private patio. Upstairs, find two inviting bedrooms, including a primary suite with a walk-through closet. The skylight brightens the space, and residents enjoy access to great amenities like pools, a clubhouse, and tennis courts. A delightful lifestyle awaits in this pet-friendly home!

44 High St Apt 134 #134 - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

APARTMENT - Chester, NY

44 High St Apt 134 #134, Chester, NY 10918

In-unit laundry | Air conditioning | High ceilings

1 bed

1 bath

$2,000

Apartment for rent

Bright & Spacious 1-Bed Apartment with Scenic Views

Experience comfort and style in this inviting 1-bedroom, 1.5-bathroom apartment boasting 970 sq ft of living space. The third-floor unit features soaring 9-foot ceilings, gorgeous granite counters in the kitchen, and in-unit laundry for convenience. Relax on the deck and savor stunning views of the Sugar Loaf Mountains. Enjoy central A/C, large closets, and proximity to shopping and transportation, all just an hour from NYC.

338 Clove Rd - Photo 1 of 1

15m ago

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Verified

338 Clove Rd, Monroe, NY 10950

In-unit laundry | Furnished | Air conditioning

3 beds

3 baths

$6,102

Apartment for rent

457 Clove Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

457 clove

457 Clove Rd, Monroe, NY 10950

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

4 beds

2 baths

$3,100

Apartment for rent

Available Mar 5

321 Museum Village Rd - Photo 1 of 1

15m ago

Our team has verified this company

Verified

321 Museum Village Rd, Monroe, NY 10950

In-unit laundry | Furnished | Air conditioning

5 beds

4 baths

$16,003

$12,775

Price drop

Apartment for rent

1099 State Route 17m - Photo 1 of 1

20m ago

Our team has verified this company

Verified

1099 State Route 17m, Monroe, NY 10950

In-unit laundry | Furnished | Air conditioning

4 beds

2 baths

$8,679

Apartment for rent

Find sweet deals near Chester

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

23 Laurel Trl - Photo 1 of 1

7h ago

House for rent in Monroe

23 Laurel Trl, Monroe, NY 10950

In-unit laundry | Hardwood floor | Fireplace

4 beds

2 baths

$2,300

House for rent

Available Mar 16

4 Sunrise Trl - Photo 1 of 1

7h ago

House for rent in Monroe

4 Sunrise Trl, Monroe, NY 10950

In-unit laundry | Balcony | Hardwood floor

3 beds

1 bath

$2,300

House for rent

Available Mar 16

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35 Peddler Hill Rd - Photo 1 of 1

18h ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

35 Peddler Hill Rd, Monroe, NY 10950

In-unit laundry | Hardwood floor | Storage

3 beds

1 bath

$2,700

House for rent

1d ago

Condo for rent in Monroe

20 Peddler Hill Rd Apt 2002, Monroe, NY 10950

1 bed

1 bath

$1,800

Condo for rent

157 State Route 17m - Photo 1 of 1

3d ago

House for rent in Harriman

SINGLE_FAMILY - Harriman, NY

157 State Route 17m, Harriman, NY 10926

In-unit laundry | Storage | Fireplace

3 beds

1 bath

$3,350

House for rent

210 Cromwell Hill Rd #2 - Photo 1 of 1

5d+ ago

Apartment for rent in Monroe

Water Etc. Studio In Monroe! Move-In Ready

210 Cromwell Hill Rd #2, Monroe, NY 10950

Hardwood floor | Outdoor space

1 bed

1 bath

$1,400

Apartment for rent

Available Mar 31

129 Spring St - 127 Spring St. 202 - Photo 1 of 1

5d+ ago

Apartment for rent in Monroe

The Clove at Spring Street LLC - 127 Spring St. 202

129 Spring St - 127 Spring St. 202, Monroe, NY 10950

3 beds

2 baths

$3,200

Apartment for rent

Available Apr 1

83 Lake Region Blvd - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

83 Lake Region Blvd, Monroe, NY 10950

In-unit laundry | On-site laundry | Fitness center

3 beds

2 baths

$4,200

$3,850

Price drop

House for rent

234 Prospect Rd - Photo 1 of 1

5d+ ago

Apartment for rent in Monroe

234 prospcts

234 Prospect Rd, Monroe, NY 10950

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

1 bed

1 bath

$1,700

Apartment for rent

Available Mar 10

Showing 1 - 25 of 25 results
Home > Apartments in Chester
Updated: March 17, 2026

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Learn more about renting in Chester, NY

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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.

Chester, NY apartment availability

Chester's rental market has a relatively limited selection of listings, with an average of 24 available per month. The most common apartment sizes are 2-bedroom and 1-bedroom units, each accounting for approximately 33% and 29% of the total market, respectively, followed closely by 3-bedroom apartments at 29%. Studios are relatively scarce, making up only 4% of the market. Many Chester apartments offer desirable amenities, with in-unit laundry being a standout feature, available in 71% of listings. Air conditioning and dishwashers are also common perks, found in 54% of apartments. These figures are based on historical data, but they should give you a sense of what to expect in the current market. Renters in Chester will need to be prepared to act quickly when a suitable apartment becomes available.

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 2024 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.

Apartment rentals Chester, NY FAQ

What is the average size of an apartment in Chester, NY?

The average size of a 1 bedroom apartment rental in Chester is 799 square feet. The average size of a 2 bedroom apartment rental in Chester is 1000 square feet. The average size of a 3 bedroom apartment rental in Chester is 2840 square feet.

Can I afford an apartment for rent in Chester, NY?

To help you better understand how much rent you can afford, check out Zumper's rent calculator. Our rent calculator can help you learn more about Chester average rent prices.

Looking for apartments in Chester, NY near you?

🔑Available apartment rentals25
💰Best rent deal210 Cromwell Hill Rd #2
Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos