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Houses for Rent in Chester, NY

All rentals

3 Brookside Ave - Photo 1 of 1

5d+ ago

House for rent in Chester

Residential Lease, Chester, NY

3 Brookside Ave, Chester, NY 10918

In-unit laundry | Business center

3 beds

2.5 baths

$4,200

House for rent

20 Goshen Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

Residential Lease, Chester, NY

20 Goshen Rd, Chester, NY 10918

In-unit laundry | Garage parking | High ceilings

4 beds

2.5 baths

$6,000

House for rent

Colonial 4-bed estate with horse trails & orchard

Quietly set in Chester, NY, this colonial-style 4-bed, 2.5-bath house spans 3,348 sqft on expansive grounds with private horse trails and a mature fruit orchard. The custom home features hardwood floors, high ceilings, central air, and a 3-car garage with 10-foot doors. An outdoor wood-burning furnace adds cost savings, while the brick exterior and 14 rooms provide ample space for those seeking a self-sufficient lifestyle with modern amenities.

43 Tephanic Ave - Photo 1 of 1

4h ago

House for rent in Monroe

43 Tephanic Ave, Monroe, NY 10950

Outdoor space | Garage parking | Hardwood floor

4 beds

2.5 baths

$4,200

House for rent

402 Mountain Laurel Dr - Photo 1 of 1

2d ago

Townhouse for rent in Monroe

Residential Lease, Monroe, NY

402 Mountain Laurel Dr, Monroe, NY 10950

In-unit laundry | Outdoor space | Swimming pool

3 beds

2.5 baths

$3,300

House for rent

28 Hidden Creek Blvd - Photo 1 of 1

2d ago

Townhouse for rent in Monroe

Residential Lease, Monroe, NY

28 Hidden Creek Blvd, Monroe, NY 10950

In-unit laundry | Outdoor space | Garage parking

3 beds

3.5 baths

$3,999

House for rent

649 Lakes Rd - Photo 1 of 1

5d+ ago

House for rent in Monroe

Residential Lease, Monroe, NY

649 Lakes Rd, Monroe, NY 10950

In-unit laundry | Outdoor space | Furnished

1 bed

1 bath

$2,100

House for rent

60 W Jeanibo Rd - Photo 1 of 1

5d+ ago

House for rent in Monroe

Residential Lease, Monroe, NY

60 W Jeanibo Rd, Monroe, NY 10950

Garage parking | Dishwasher

3 beds

1 bath

$2,850

House for rent

12 Lake Region Blvd - Photo 1 of 1

5d+ ago

House for rent in Monroe

Residential Lease, Monroe, NY

12 Lake Region Blvd, Monroe, NY 10950

In-unit laundry | Outdoor space

3 beds

1 bath

$3,100

$2,995

Price drop

House for rent

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35 Helene Rd - Photo 1 of 1

5d+ ago

Townhouse for rent in Warwick

Residential Lease, Warwick, NY

35 Helene Rd, Warwick, NY 10990

In-unit laundry | Outdoor space | Garage parking

3 beds

2.5 baths

$2,950

House for rent

16 Boxwood Rd - Photo 1 of 1

5d+ ago

House for rent in Goshen

Residential Lease, Goshen, NY

16 Boxwood Rd, Goshen, NY 10924

In-unit laundry | Outdoor space | Storage

5 beds

3 baths

$4,200

House for rent

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Find sweet deals near Chester

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

$1,500

Monroe

$2,950

Warwick

$2,350

Monroe

$1,800

Monroe

82 Walton Ter - Photo 1 of 1

5d+ ago

House for rent in Monroe

Residential Lease, Monroe, NY

82 Walton Ter, Monroe, NY 10950

Outdoor space | Storage | Garage parking

4 beds

2 baths

$3,700

House for rent

256 Heritage Ln - Photo 1 of 1

5d+ ago

Townhouse for rent in Monroe

Residential Lease, Monroe, NY

256 Heritage Ln, Monroe, NY 10950

In-unit laundry | Outdoor space | Garage parking

3 beds

2.5 baths

$3,275

House for rent

Listings within 10 miles
4 Fleetwood Dr - Photo 1 of 1

4h ago

House for rent in Goshen

Residential Lease, Goshen, NY

4 Fleetwood Dr, Goshen, NY 10924

In-unit laundry | Outdoor space | Hardwood floor

4 beds

2 baths

$2,200

House for rent

44 Orchard Lake Dr #NA - Photo 1 of 1

3d ago

House for rent in Monroe

Beautiful Private House for Rent!

44 Orchard Lake Dr #NA, Monroe, NY 10950

In-unit laundry | Outdoor space | Hardwood floor

3 beds

2 baths

$3,000

House for rent

Available Aug 24

87 Arcadian Trl - Photo 1 of 1

5d+ ago

House for rent in Monroe

Cottage style home, 3 Beds, 1 Bath with lots of upgraded ammenities.

87 Arcadian Trl, Monroe, NY 10950

In-unit laundry | Outdoor space | Fireplace

3 beds

1 bath

$2,500

House for rent

Available Sep 1

1093 Orange Tpke - Photo 1 of 1

5d+ ago

House for rent in Monroe

House for rent

87 Sylvan Trl - Photo 1 of 1

5d+ ago

House for rent in Monroe

4 Bedroom 1 Bathroom Renovated House For Rent

87 Sylvan Trl, Monroe, NY 10950

In-unit laundry | Fireplace | Dishwasher

4 beds

1 bath

$2,350

House for rent

Available Aug 1

25 Gloria Trl - Photo 1 of 1

5d+ ago

House for rent in Monroe

Residential Lease, Monroe, NY

25 Gloria Trl, Monroe, NY 10950

Outdoor space | Ceiling fan

1 bed

1 bath

$2,400

House for rent

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33 Oakwood Trl S - Photo 1 of 1

5d+ ago

House for rent in Monroe

33 Oakwood

33 Oakwood Trl S, Monroe, NY 10950

In-unit laundry | Deck | Storage

2 beds

1 bath

$1,800

House for rent

Available Aug 1

131 Hill Rd - Photo 1 of 1

1d ago

House for rent in Goshen

131 Hill Rd, Goshen, NY 10924

In-unit laundry | Outdoor space | Garage parking

2 beds

2 baths

$2,800

House for rent

3 Canterbury Ln - Photo 1 of 1

1d ago

House for rent in Warwick

3 Canterbury Ln, Warwick, NY 10990

In-unit laundry | Outdoor space | Garage parking

4 beds

2.5 baths

$7,500

House for rent

75 Forester Ave #225 - Photo 1 of 1
New construction

3d ago

Townhouse for rent in Warwick

Residential Lease, Warwick, NY

75 Forester Ave #225, Warwick, NY 10990

In-unit laundry | Outdoor space | Storage

1 bed

1 bath

$2,675

House for rent

Listings within 20 miles
15 Forge Hill Rd - Photo 1 of 1

5d+ ago

House for rent in New Windsor

Residential Lease, New Windsor, NY

15 Forge Hill Rd, New Windsor, NY 12553

In-unit laundry | Storage | Hardwood floor

3 beds

1 bath

$2,975

House for rent

103 N Beacon St - Photo 1 of 1

4h ago

House for rent in Middletown

103 N Beacon St, Middletown, NY 10940

Outdoor space

3 beds

2 baths

$1,500

House for rent

3 Cedar Hill Dr - Photo 1 of 1

3d ago

Townhouse for rent in Middletown

Residential Lease, Middletown, NY

3 Cedar Hill Dr, Middletown, NY 10940

In-unit laundry | Storage | Garage parking

3 beds

3.5 baths

$3,600

House for rent

Showing 1 - 25 of 25 results
Home > House Rentals in Chester
Updated: August 28, 2026

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Knollcrest Village
The Brewery
The Regency Club

Apartments for rent in Chester6 rentals

6 rentals

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Discover houses for rent in Chester, NY

🌇Available house rentals25 houses
💰Best rent deal649 Lakes Rd
⭐Popular amenities, ,
👚With laundry facilities
🍽With dishwasher
🚗With garage parking
🏠With photos