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Apartments for Rent in Chester, NY

Average rent

$2,300
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208 Glenmere Rd - Photo 1 of 1

5d+ ago

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208 glemere

208 Glenmere Rd, Chester, NY 10918

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

5 beds

3 baths

$3,400

$3,100

Price drop

Apartment for rent

Available Apr 17

Spacious Home with Huge Garage & 5 Bedrooms

This well-maintained 5-bedroom, 3-bathroom home offers spacious living in a peaceful setting. The bright living room is perfect for entertaining, while the large detached garage provides ample storage and workshop space. Enjoy modern conveniences along with a welcoming atmosphere — ready for immediate move-in. Ideal for families or anyone needing extra room to breathe!

4 Ayr Rd - Photo 1 of 1

23h ago

House for rent in Chester

4 Ayr Rd, Chester, NY 10918

Garage parking | Dishwasher

6 beds

4.5 baths

$4,300

House for rent

5 Laroc Rd - Photo 1 of 1

5d+ 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!

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

Contemporary Ranch with Stunning Mountain Views

Experience elevated living in this fully furnished 3,412 sq ft contemporary ranch nestled on 1.2 acres, featuring breathtaking mountain views. The chef's kitchen, bright open layout, and cozy fireplace make it perfect for year-round entertaining. Enjoy an expansive primary suite, a game room, and a lovely sunroom. Outdoor amenities include a hot tub, oversized deck, and firepit, ideal for relaxation. This home is a tranquil retreat just an hour from NYC, close to parks, breweries, and dining options.

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

Luxurious Estate with Horse Trails & Orchard

This stunning 4-bedroom, 3-bath Colonial home offers a unique blend of luxury and self-sufficiency. Spanning 3,348 sq. ft., the estate features expansive grounds with private horse trails and a mature fruit orchard. Practicalities include an oversized 3-car garage with high-clearance doors and an efficient outdoor wood-burning furnace. Retreat to this serene sanctuary in Orange County, while enjoying easy access to local transit and shopping. Perfect for horse lovers and outdoor enthusiasts alike.

204 Pine Hollow Way - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

1 bed

1 bath

$1,750

Apartment for rent

Bright and Spacious One-Bedroom Retreat

This highly desirable one-bedroom apartment boasts an open-concept layout filled with natural light and a private patio for serene outdoor relaxation. With a large bedroom offering great closet space and convenient in-unit laundry hook-ups, the 1,000 sq ft unit ensures comfort and ease. Located near shopping, dining, and the scenic beauty of the Hudson Valley, it's perfect for commuters with express bus access to NYC. Don't miss this must-see opportunity!

208 Glenmere Rd #1 - Photo 1 of 1

5d+ ago

House for rent in Chester

208 Glenmere Road - 1

208 Glenmere Rd #1, Chester, NY 10918

5 beds

2.5 baths

$3,400

House for rent

Available Mar 18

Charming Country Cottage with Updated Features

This delightful 5-bedroom, 2.5-bath country cottage spans nearly 1,815 square feet and is nestled on a tranquil one-acre lot. The property showcases an eat-in kitchen, a cozy dining room, and fresh renovations including updated flooring, windows, and appliances. Experience the unique charm of this "Hamptons" style cottage, complete with a spacious 3-car detached garage. Enjoy peaceful living on a lightly traveled road, perfect for relaxation and escape from the hustle and bustle.

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.

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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 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.

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Walk-In Closets

Hardwood Floor

Dishwasher

In-Unit Laundry

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

9 Summit Pl - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

9 SUMMITPl

9 Summit Pl, Monroe, NY 10950

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

4 beds

2 baths

$3,600

$3,300

Price drop

Apartment for rent

Available Apr 16

57 School Rd - Photo 1 of 1

1d ago

House for rent in Monroe

SINGLE_FAMILY - Colonial - Monroe, NY

57 School Rd, Monroe, NY 10950

In-unit laundry

4 beds

2 baths

$3,500

House for rent

7 Kennedy Ln #3 - Photo 1 of 1

1d ago

Apartment for rent in Monroe

1 Bedroom with Extra Room, Backyard & Parking

7 Kennedy Ln #3, Monroe, NY 10950

Hardwood floor | Storage | Outdoor space

1 bed

1 bath

$2,100

Apartment for rent

Available May 1

79 Quaker Hill Rd #2 - Photo 1 of 1

2d ago

Apartment for rent in Monroe

MULTI_FAMILY - Monroe, NY

79 Quaker Hill Rd #2, Monroe, NY 10950

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

4 beds

2 baths

$3,300

Apartment for rent

60 Evan Rd - Photo 1 of 1

5d+ ago

Townhouse for rent in Warwick

SINGLE_FAMILY - Warwick, NY

60 Evan Rd, Warwick, NY 10990

Garage parking | Hardwood floor | Storage

3 beds

2.5 baths

$2,900

House for rent

Find sweet deals near Chester

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

241 N Main St #2 - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Colonial - Monroe, NY

241 N Main St #2, Monroe, NY 10950

Outdoor space

2 beds

1 bath

$1,600

House for rent

111 N Main St #2 - Photo 1 of 1

5d+ ago

Apartment for rent in Monroe

APARTMENT - Colonial - Monroe, NY

111 N Main St #2, Monroe, NY 10950

Assigned parking

1 bed

1 bath

$1,250

Apartment for rent

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7 Autumn Trl #A - Photo 1 of 1

5d+ ago

Apartment for rent in Goshen

APARTMENT - Goshen, NY

7 Autumn Trl #A, Goshen, NY 10924

On-site laundry

3 beds

2 baths

$2,950

Apartment for rent

Listings within 10 miles
260 W Main St #16 - Photo 1 of 1

11h ago

Apartment for rent in Goshen

APARTMENT - Goshen, NY

260 W Main St #16, Goshen, NY 10924

In-unit laundry | Air conditioning | Assigned parking

2 beds

2 baths

$3,295

Apartment for rent

10 Candlewood Rd - Photo 1 of 1

3d ago

House for rent in Harriman

SINGLE_FAMILY - Split Level - Harriman, NY

10 Candlewood Rd, Harriman, NY 10926

In-unit laundry | Furnished | Garage parking

4 beds

3 baths

$3,900

House for rent

5 Woodland Cir S - Photo 1 of 1

5d+ ago

House for rent in Monroe

Charming 1-Bedroom Single Family Home with Large Yard

5 Woodland Cir S, Monroe, NY 10950

Fireplace | Outdoor space

1 bed

1 bath

$1,750

House for rent

Available Apr 20

28 Ford Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Monroe

CONDOS - Monroe, NY

28 Ford Ct, Monroe, NY 10950

In-unit laundry | Garage parking | Swimming pool

3 beds

2.5 baths

$3,700

House for rent

11 Upper Hillman Rd - Photo 1 of 1

5d+ ago

House for rent in Warwick

SINGLE_FAMILY - Warwick, NY

11 Upper Hillman Rd, Warwick, NY 10990

In-unit laundry | Storage | Outdoor space

2 beds

2 baths

$2,300

House for rent

90 Greenwich Ave #201 - Photo 1 of 1
New construction

5d+ ago

Apartment for rent in Goshen

APARTMENT - Goshen, NY

90 Greenwich Ave #201, Goshen, NY 10924

In-unit laundry | Dishwasher

1 bed

1 bath

$1,950

Apartment for rent

Showing 1 - 25 of 25 results
Home > Apartments in Chester
Updated: May 2, 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 772 square feet. The average size of a 2 bedroom apartment rental in Chester is 946 square feet. The average size of a 3 bedroom apartment rental in Chester is 1834 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 deal111 N Main St #2
Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos