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Chester, NY Homes for Rent

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  • /20

    $6,920 per month

    • 7 Beds
    • 5 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918

    Escape to this luxurious 7-bedroom retreat in the heart of Chester, NY! Designed for ultimate relaxation, the home boasts upscale outdoor spaces with a sparkling pool, porch lounge, and covered dining area. Inside, enjoy stylish furnishings, a chic home office, and elegant touches throughout. A game room with a pool table adds a fun element, making this the perfect mix of comfort and

    45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918
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    $2,100 per month

    • 2 Beds
    • 1 Bath
    • 1,258 Sq Ft
    • Apartment for Rent

    15 Railroad Ave Unit 2, Chester, NY 10918

    FANTASTIC and huge 2 bedroom apartment in the heart of the historic Village of Chester. A third floor unit in the historic American House (a former hotel) -- and with either first or second floor access -- with lots of windows for great natural light, and hardwood floors throughout. CENTRAL AIR! Approx. 1,258 square feet, along with a HUGE walk-up attic. There's a small third room which can be an

    Dean Diltz Keller Williams Realty

    15 Railroad Ave Unit 2, Chester, NY 10918
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    $1,700 per month

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

    13 Railroad Ave, Chester, NY 10918

    FANTASTIC and huge 1 bedroom apartment in the heart of the historic Village of Chester. A second floor unit in the historic American House (a former hotel) with lots of windows for great natural light, and hardwood floors throughout. Private entrance which includes large closet for storage -- then up the stairs to the apartment. Tenant responsible for electric & heat(and Internet/cable/phone,

    Dean Diltz Keller Williams Realty

    13 Railroad Ave, Chester, NY 10918
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    $2,500 per month

    • 2 Beds
    • 1.5 Baths
    • 1,076 Sq Ft
    • Townhouse for Rent

    1417 Whispering Hills Unit 156, Chester, NY 10918

    This newly rebuilt townhouse in Whispering Hills is now available for rent after being completely renovated following a fire. The rental features a spacious living room with tiled flooring and a cozy fireplace, along with a modern Shaker-style kitchen that boasts new cabinetry and brand-new appliances. On the main level, you will find a laundry room and a half bathroom for added

    Jay Himelson Howard Hanna Rand Realty

    1417 Whispering Hills Unit 156, Chester, NY 10918
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    $2,500 per month

    • 1 Bed
    • 1 Bath
    • 1,768 Sq Ft
    • House for Rent

    21 Murray Dr, Chester, NY 10918

    Introducing a wonderfully spacious one-bedroom apartment on the bottom floor, which offers an impressive 1768 square feet of living space. This apartment features a generously sized bedroom, plenty of closet space and storage, an updated eat-in kitchen with granite countertops, stainless steel appliances, and a full bath, ensuring comfort and convenience. Laundry facilities are available in the

    Carla Terranova Keller Williams Realty

    21 Murray Dr, Chester, NY 10918
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    $3,800 per month

    • 4 Beds
    • 2.5 Baths
    • 2,166 Sq Ft
    • House for Rent

    14 Lori Ln, Chester, NY 10918

    THE RENTAL YOU HAVE BEEN LOOKING FOR! Beautiful, well-kept fabulous home in beautiful neighborhood Monroe Woodbury School district. Gorges kitchen with appliances, spacious rooms, ample living space, and expansive backyard to enjoy all year round, Great location! Close to many major shopping areas and highways. This lovely home has all your needs. Call today, before it’s gone!

    Michael Pollak Master Realty Group Inc.

    14 Lori Ln, Chester, NY 10918
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    $2,450 per month

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft
    • Townhouse for Rent

    2507 Whispering Hills, Chester, NY 10918

    Prime Rental Opportunity in Whispering Hills! Unit Features: • 2 spacious bedrooms • Skylight on second floor • 1.5 modern bathrooms • Cozyfireplace • In-unit washer and dryer • 2 car garage • Private outside fenced patio Community Amenities: • Refreshing swimming pool • Fun-filledplayground for kids • Tennis court for sports enthusiasts • Close proximity to scenic hiking and biking

    Barbara Korabel Four Seasons Realty Group

    2507 Whispering Hills, Chester, NY 10918
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    $1,600 per month

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

    26 Main St Unit C, Chester, NY 10918

    Live in the heart of historic Chester! This beautiful third floor 1-bedroom, 1-bath apartment is located right on Main Street. Featuring tons of natural light and a private back deck it's the perfect retreat in a vibrant village setting. You'll be steps away from coffee shops, restaurants, and the Heritage Trail, making it easy to enjoy everything Chester has to offer. Commuters will love the

    Brooke Lorimer Keller Williams Realty

    26 Main St Unit C, Chester, NY 10918
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    $750 per month

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

    7915 State Route 9 Unit 2, Chester, NY 12860

    Basic 1BR/1BA apartment Pottersville! This unit has a large porch and semi-private yard. Exceptionally easy to access from I-87, close to skiing, 20 minutes to Gore, 25 minutes to Lake George. Heat, hot water, sewer and water included in rent. Landlord plows parking lot, tenant is responsible for their walkway. SF estimated. No smoking, no pets. 3x income and renter's insurance required. This

    Jonathan Van Dyk Equitas Realty

    7915 State Route 9 Unit 2, Chester, NY 12860
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    $2,700 per month

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Apartment for Rent

    62 Main St, Chester, NY 10918

    Tons of square footage in a quiet area with amazing views. With coffe shops , entertainment and restaurants within walking distance , this rental will go quick! Ample parking, a backyard complete with play area, bamboo floors and 5 minutes from commuting highways make this place a unicorn in the real estate world. Come check it out!

    Ryan Case Keller Williams Realty

    62 Main St, Chester, NY 10918
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    $3,050 per month

    • 3 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • House for Rent

    46 Midway Dr, Monroe, NY 10950

    THE RENTAL YOU HAVE BEEN LOOKING FOR! Beautiful, well-kept fabulous two story home in the Monroe Woodbury School district. Spacious rooms, updated kitchen with plenty of cabinets, four season room fully equipped with new windows and heater can used as office, ample living space, and expansive backyard to enjoy all year round. This lovely home comes with lake rights and all your needs. Call today,

    Eliezer Safdie Sage Realty Center LLC

    46 Midway Dr, Monroe, NY 10950

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 neighborhoods in Chester, NY for renters?
The most popular neighborhoods in Chester, NY for renters are Blooming Grove, Woodbury, Wallkill, New Windsor and Cornwall.
What are the most popular zip codes in Chester, NY for renters?
The most popular zip codes in Chester, NY for renters include 10918, 10950, 10990, 10924 and 10926.
How to Rent a Home