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Chester 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
  • /20

    $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
  • /33

    $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
  • /25

    $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
  • /16

    $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
  • /14

    $1,700 per month

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

    108 Pine Hollow Way, Chester, NY 10918

    Highly desirable large and luxurious one bedroom apartment for rent! Spacious open concept unit with lots of natural light! Enjoy your gas fireplace and create a lovely ambiance and keep cozy. Relax on your own private patio and enjoy the peaceful surroundings of the outdoors. Large bedroom with double walk-in closets! This unit has a private laundry room with hook ups. Close to all shopping,

    Kristie Jacques Century 21 Full Service Realty

    108 Pine Hollow Way, Chester, NY 10918
  • /46

    $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
  • /36

    $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
  • /14

    $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
  • /35

    $2,950 per month

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

    1421 Whispering Hills, Chester, NY 10918

    Step into comfort and style in this beautifully renovated end unit, where modern design meets everyday convenience. Featuring 3 spacious bedrooms, 2.5 sleek bathrooms, and a stunning kitchen with quartz countertops and stainless steel appliances, this home is made for relaxed living and effortless entertaining.Cozy up by the fireplace in the inviting living room, enjoy the convenience of

    Dennis Clark Howard Hanna Rand Realty

    1421 Whispering Hills, Chester, NY 10918
  • /15

    $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
  • /22

    $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

Frequently Asked Questions Why Live in Chester

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