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Chester, NY Homes for Rent

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  • /29

    $2,400 per month

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Townhouse for Rent

    3917 Whispering Hills, Chester, NY 10918

    TWO-LEVEL RENTAL in Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances as well as a convenient in-unit washer and dryer. The first level offers a stylish half bath and brand-new flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio.

    Agent Photo

    Hazel Cello

    Keller Williams Hudson Valley

    (845) 460-1589

    3917 Whispering Hills, Chester, NY 10918
  • /20

    $12,024 per month

    • 7 Beds
    • 6 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

    The advertised rate of $12,025/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 7, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918
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    $1,750 per month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    204 Pine Hollow Way, Chester, NY 10918

    Highly desirable one bedroom apartment for rent! Spacious open concept unit with lots of natural light! Relax on your own private patio and enjoy the peaceful surroundings of the outdoors. Large bedroom with great closet space! This unit has a private laundry room with hook ups. Close to all shopping, restaurants, apple picking, wineries, breweries & everything the beautiful Hudson Valley has to

    Kristie Jacques Century 21 Full Service Realty

    204 Pine Hollow Way, Chester, NY 10918
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    $3,400 per month

    • 5 Beds
    • 2.5 Baths
    • 1,815 Sq Ft
    • House for Rent

    208 Glenmere Rd, Chester, NY 10918

    A charming country cottage is available for rent and is situated on a picturesque country road. The main level features an eat-in kitchen, dining room, and two bedrooms, while the upper level has three bedrooms. The cottage boasts updated flooring, windows, kitchen, and heating. The interior has been freshly painted, and new appliances and flooring have been added in 2021. The older "Hamptons"

    Abraham Schwartz Priority Management

    208 Glenmere Rd, Chester, NY 10918
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    $3,200 per month

    • 3 Beds
    • 2.5 Baths
    • 1,670 Sq Ft
    • Townhouse for Rent

    404 Mountain Laurel Dr, Monroe, NY 10950

    Welcome to this beautifully maintained and updated 3 bedroom 2 and a half bath end-unit condo offering comfort, style, and scenic surroundings. This spacious home features a bright and open layout designed for both everyday living and entertaining. Step inside the sun drenched living space and notice the large family room which flows seamlessly into the dining area and kitchen. Your kitchen is

    Nicholas Carbone HomeSmart Homes & Estates

    404 Mountain Laurel Dr, Monroe, NY 10950
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    $2,800 per month

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • House for Rent

    71 Greycourt Rd, Chester, NY 10918

    Lovely and Private! Welcome to 71 Greycourt rd. this house is conveniently located just in the right location being close to major highways and shopping! This home was recently renovated with lots of upgrades. nice size kitchen, upgraded electricity, and much more! This house is private, sitting on a 2-acre property and a fenced-in yard for total privacy. This house is your dream rental! Don't

    Mordechai Ungar HFA Realty Group

    71 Greycourt Rd, Chester, NY 10918
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    $3,800 per month

    • 4 Beds
    • 3 Baths
    • 2,457 Sq Ft
    • House for Rent

    118 Booth Rd, Chester, NY 10918

    A tastefully, restored 2-story, 4BR, 3BTH, bi-level style home set on over 3+ prestine acres at the end of a quaint cul-de-sac. Enjoy the large open fields, secluded from all the stresses of the day. Plenty of room for an athletic field, in-ground pool or just a peaceful sanctuary. The exquisite touches throughout add to its elegance, from high-end ceramics to restored oak floors. The

    Chris Scibelli Keller Williams Realty

    118 Booth Rd, Chester, NY 10918
  • /10

    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Townhouse for Rent

    82 High St Unit 5, Chester, NY 10918

    Very bright and spacious top-floor Penthouse apartment! Come see this open layout floorplan. The updated kitchen has a new stainless steel refrigerator and dishwasher. The Primary bedroom has large double closets and can accommodate a king-size bed. The living room/dining room combination is bright and sun-filled, with plenty of windows and an outside deck. You’ll appreciate the convenience of

    Lynda Hoss Weichert Realtors

    82 High St Unit 5, Chester, NY 10918
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    $1,500 per month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    8 Main St, Chester, NY 10918

    Located in Historic Downtown Chester. This is a 1 bedroom apartment located on the 2nd floor. Open floor plan with exposed brick walls and lots of natural light. Walking distance to shops, restaurants, brewery, and the Heritage Trail. Close to public transportation and Route 17.

    Jeanmarie Valentin HomeSmart Homes & Estates

    8 Main St, Chester, NY 10918
  • /9

    $2,000 per month

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    1396 Kings Hwy, Chester, NY 10918

    Newly renovated 3 bedroom unit located in the heart of Sugar Loaf and within the Warwick School District. This second-floor walkup features a bright white kitchen with stainless steel appliances, including an in-unit washer/drier, and offers a large private balcony with scenic views of Sugar Loaf Mountain. The unit is situated above a restaurant; music may be audible as late as 11 PM on Friday

    Roxanne Hartman Timothy W. Kramer

    1396 Kings Hwy, Chester, NY 10918
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    $3,050 per month

    • 4 Beds
    • 1.5 Baths
    • 1,605 Sq Ft
    • House for Rent

    98 Main St, Chester, NY 10918

    Welcome to 98 Main St: a gracious Colonial in the center of the village of Chester!A huge "wrap-around" front porch greets you when you arrive. Once inside, you will be impressed with the "old world" charm of the stained-glass windows, dark wood trim, Hardwood floors and the pocket doors in the Living Room. Many large windows downstairs let in plenty of sunlight! Upstairs there are 4 nice

    Eveline White Hudson Valley Griffith

    98 Main St, Chester, NY 10918
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    $2,850 per month

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Townhouse for Rent

    4321 Whispering Hills, Chester, NY 10918

    This is a beautiful rental, If you are looking to rent, here it is!! plenty of room,3 bedrooms 2.5 baths, 2 car garage, close to amenities, new bathrooms, close to shopping, close to major highways and rail for commuters. Freshly painted, new carpets, hardwood floors redone. Must see if you are looking to rent!!! Additional Information: ParkingFeatures:1 Car Attached.

    Dan Neil Field Pointe Realty LLC

    4321 Whispering Hills, Chester, NY 10918
  • /19

    $1,900 per month

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    2 Oak St, Chester, NY 10918

    Freshly updated and well-maintained 2 bedroom unit in a multi-family home. Open concept living space with kitchen, dining space and living room. Beautiful view of the Chester farmlands from the living room. Two nicely sized bedrooms with large closets. Separate entrance for tenant, access to side yard in front of unit, tenant gets space in the driveway for 2 cars. Landlord pays heat, hot water,

    Elissa Elliott Howard Hanna Rand Realty

    2 Oak St, Chester, NY 10918
  • /2

    $3,850 per month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Apartment for Rent

    408 Bull Mill Rd Unit 2, Chester, NY 10918

    Experience peaceful country living at 408 Bull Mill Rd, Unit 2, a Victorian-style retreat set on sprawling acreage and surrounded by nature. This 1,800 sq. ft. home offers exceptional privacy, quiet, and seclusion while providing the space and charm of a classic design. Inside, you’ll find three spacious bedrooms and two full bathrooms, thoughtfully laid out to maximize comfort and natural light.

    Robert Addon Keller Williams Realty

    408 Bull Mill Rd Unit 2, Chester, NY 10918
  • /20

    $2,700 per month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Property for Rent

    112 Scott St, Monroe, NY 10950

    A truly charming place to call home! Beautiful open concept home for rent featuring an airy floor plan with abundant windows that fill the space with natural light. This inviting property offers a lovely dining area, a spacious primary bedroom with its own private bath, and generous closet space thru-out, a washer/dryer, a nice relaxing deck and so much more. The home can be rented partially

    Sy Mujovic I Realty LLC

    112 Scott St, Monroe, NY 10950
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    $3,650 per month

    • 3 Beds
    • 2 Baths
    • 1,793 Sq Ft
    • House for Rent

    83 Lake Region Blvd, Monroe, NY 10950

    3 bedroom, 2 bathroom house for rent in the perfect location near Walton Lake. 4th room can be used as a bedroom, office or gym. Huge fenced in yard. 2 driveways with plenty space and storage. Central Air, Laundry, ring surveillance, corner lot, walking distance to lake. Fully furnished!

    Wendy Todoric Keller Williams Realty

    83 Lake Region Blvd, Monroe, NY 10950
  • /7

    $2,700 per month

    • 3 Beds
    • 2.5 Baths
    • 1,452 Sq Ft
    • House for Rent

    47 Helene Rd, Warwick, NY 10990

    Great spacious end unit townhouse in Kings Estates ! Freshly painted with professionally cleaned carpets makes this townhouse move in ready! This unit has been renovated within the last few years and includes newer stainless steel appliances and hardwood floors throughout the living and dining room. Back deck off of the dining room and kitchen area offers a GREAT view. Must see to appreciate !

    Christina Biagini Weichert Realtors

    47 Helene Rd, Warwick, NY 10990

Why Live in Chester

Chester, NY, is a rural town with a rich history in the dairy industry, famously known as the birthplace of Philadelphia-style cream cheese. Located minutes from Hudson Valley attractions and retail centers in Woodbury, Chester offers a mix of small-town single-family homes and larger farmhouses on multi-acre lots. The town is accessible via Route 17, making it a convenient location with relatively lower home prices compared to nearby towns like Monroe. Chester features diverse recreational options, including the family-friendly Castle Fun Center with carnival rides, mini golf, and an indoor roller-skating rink. Carpenter Community Park serves as the town's central green space, offering a playground, picnic pavilion, and sports courts, while Goosepond Mountain State Park provides 1,500 acres of trails for hiking and horseback riding. The Orange Heritage Trail, accessible from the historic Erie Depot, runs almost 20 miles through the county. Local attractions include Legoland in nearby Goshen and the Capelli Sports Complex. Chester Mall offers grocery shopping at ShopRite and movies at Flagship Premium Cinemas, while the Chester Agricultural Center provides farm-fresh produce. Dining options include the Rustic Wheelhouse Restaurant, known for its Italian cuisine. Homes in Chester range from older, smaller houses to larger contemporary and Craftsman-style homes on spacious lots. The Windridge Mews condo subdivision offers two to three-bedroom units. The Chester Union Free School District serves the town, with Chester Elementary and Chester Academy providing various after-school activities. Commuters can reach New York City or Newark in about an hour and a half via Interstate 87 or Coach USA buses.

Frequently Asked Questions

What are the most popular zip codes in Chester, NY for renters?
The most popular zip codes in Chester, NY for renters include 10918, 10990, 10950, 10924 and 10987.
How to Rent a Home