47 Houses for Rent in Chester, New York

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Discover Houses for Rent in Chester, NY 

Chester is a town in Orange County, N.Y., in the southeastern part of the state, about 60 miles northwest of New York City. Near Monroe and Goshen, Chester is a residential community in a rural region. There are plenty of suburban neighborhoods as well as farms close to Chester. Homes for rent in Chester are perfect for families looking to get away from the bustling cities in the south. Chester is great for young kids because of the plentiful outdoor recreational opportunities. The Rock Sports Park, Chester Commons Park and Community Park offer space for families to play soccer, tennis, baseball and most other sports.

Important Information for Future Renters

  • Chester is a safe and friendly town that includes the hamlet Sugarloaf and a village also called Chester. 
  • Philadelphia-style cream cheese, the now-famous bagel topping, was first created in Chester by dairy farmer William Lawrence. It was named after the Pennsylvania city because of its reputation as a place for good food rather than any geographical relation. 
  • The area now known as Chester was first settled by the English in 1703. It's named for Chester England. 

Helpful Resources for Residents

  • Many citizens of Chester get their local news, entertainment and sports from The Chronicle, a locally published newspaper.
  • Chester's schools are part of the Chester Union Free School District, which has two schools - an elementary and a combined middle and high school. 
  • Whether you live in Sugarloaf, the village of Chester or the town, Chester's website has a lot of great information and it's easily navigable.

Live in Chester

Just an hour outside of the city, Chester doesn't sound far away. But if your family is looking to live somewhere quiet with no skyscrapers, Chester is your spot. 

Common questions asked in Chester, New York

🏠 Where can I find cheap rental houses in Chester, New York?

Check out Rentals.com's cheap rental houses in Chester. You can use our price filters to find rental houses under $1100, under $1300, under $1500, under $2000, under $2500, under $3000

🏠 How big of a rental house can I afford?

Find Studio, 1 Bedroom, 2 Bedroom, 3 Bedroom, 4 Bedroom rental houses within your budget in Chester, New York. Or you can search for houses over 600 sq.ft, 800 sq.ft, 1000 sq.ft, 1200 sq.ft, 1400 sq.ft, 2000 sq.ft.

🏠 How can I find a rental house in a specific school district?

Rentals.com was built with parents in mind. Within Chester we have 47 rental houses spread across multiple school districts. To help narrow your search, simply enter the school name within the Rentals.com search bar to find rental homes in that school district.

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