Zumper

Houses for Rent in Chester, NY

Average rent

$3,175

Track prices

Rent calculator

What can I afford?

All rentals

2104 Whispering Hls - Photo 1 of 1

5d+ ago

Townhouse for rent in Chester

CONDOS - Chester, NY

2104 Whispering Hls, Chester, NY 10918

Outdoor space | Garage parking | Walk-in closets

3 beds

2.5 baths

$2,850

House for rent

Expansive Townhouse with Fresh Renovations Awaiting

Enjoy luxurious living in this spacious 3-bedroom, 2.5-bathroom townhouse, the largest model in Whispering Hills. Undergoing renovations, it features a master suite with a private walk-in closet and a versatile layout spanning 1,331 sq. ft. Perfectly located near shopping and dining, this home combines convenient access and modern comfort, ready for move-in by April 15, 2026. Experience the ideal blend of space and sophistication in this charming community.

66 Murray Dr - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Ranch - Chester, NY

66 Murray Dr, Chester, NY 10918

In-unit laundry | High ceilings | Hardwood floor

4 beds

2 baths

$5,300

House for rent

Contemporary Ranch with Stunning Mountain Views

Experience elevated living in this fully furnished 3,412 sq ft contemporary ranch nestled on 1.2 acres, featuring breathtaking mountain views. The chef's kitchen, bright open layout, and cozy fireplace make it perfect for year-round entertaining. Enjoy an expansive primary suite, a game room, and a lovely sunroom. Outdoor amenities include a hot tub, oversized deck, and firepit, ideal for relaxation. This home is a tranquil retreat just an hour from NYC, close to parks, breweries, and dining options.

492 Black Meadow Rd Apt A #Apt A - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Other - Chester, NY

492 Black Meadow Rd Apt A #Apt A, Chester, NY 10918

Storage | Carpet | Dishwasher

1 bed

1 bath

$1,750

House for rent

Bright Ground-Level Retreat with Ample Storage

This inviting 1-bedroom, 1-bathroom rental offers a spacious and sun-filled living space on the ground level, ensuring easy access. Enjoy a well-equipped bathroom and large storage room for convenience. With 944 square feet of comfort and plenty of parking available, this home provides both privacy and functionality in a tranquil setting. Perfect for those seeking a peaceful retreat!

20 Goshen Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Colonial - 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

Luxurious Estate with Horse Trails & Orchard

This stunning 4-bedroom, 3-bath Colonial home offers a unique blend of luxury and self-sufficiency. Spanning 3,348 sq. ft., the estate features expansive grounds with private horse trails and a mature fruit orchard. Practicalities include an oversized 3-car garage with high-clearance doors and an efficient outdoor wood-burning furnace. Retreat to this serene sanctuary in Orange County, while enjoying easy access to local transit and shopping. Perfect for horse lovers and outdoor enthusiasts alike.

208 Glenmere Rd #1 - Photo 1 of 1

5d+ ago

House for rent in Chester

208 Glenmere Road - 1

208 Glenmere Rd #1, Chester, NY 10918

5 beds

2.5 baths

$3,400

House for rent

Available Mar 18

Charming Country Cottage with Updated Features

This delightful 5-bedroom, 2.5-bath country cottage spans nearly 1,815 square feet and is nestled on a tranquil one-acre lot. The property showcases an eat-in kitchen, a cozy dining room, and fresh renovations including updated flooring, windows, and appliances. Experience the unique charm of this "Hamptons" style cottage, complete with a spacious 3-car detached garage. Enjoy peaceful living on a lightly traveled road, perfect for relaxation and escape from the hustle and bustle.

118 Booth Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Contemporary - Chester, NY

118 Booth Rd, Chester, NY 10918

Storage | Swimming pool | Walk-in closets

4 beds

3 baths

$3,800

House for rent

Elegant Bi-Level Home on 3+ Serene Acres

This stunning 4-bedroom, 3-bath bi-level home offers over 2,457 sq. ft. of living space on a picturesque 3+ acre lot. Enjoy a stylish European kitchen with quartz countertops and marbled baths. The inviting open layout features high-end ceramics and restored oak floors, while the expansive outdoor space is perfect for a pool or tranquil sanctuary. With new mechanicals, windows, and roof, this exquisite property is ready to move in and enjoy a peaceful escape from the daily hustle.

Nearby rental good for eco-living

Nearby rental good for social life

948 Craigville Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

948 Craigville Rd, Chester, NY 10918

Air conditioning | Hardwood floor | Fireplace

3 beds

3 baths

$4,250

House for rent

Charming 1850s Renovated Home on 11 Acres

Experience serene country living in this beautifully renovated 1850s home set on over 11 acres. With 2,840 sq ft of space, this property features radiant heated floors, central A/C, and a stand-by generator. The lush, fenced-in pasture includes run-in sheds, perfect for horses. This home offers three bedrooms, two offices, and a loft, making it ideal for those who seek tranquility and outdoor activities. Conveniently located near shopping, dining, and attractions, it’s a perfect blend of comfort and nature.

60 W Jeanibo Rd - Photo 1 of 1

2d ago

House for rent in Monroe

SINGLE_FAMILY - Bungalow - Monroe, NY

60 W Jeanibo Rd, Monroe, NY 10950

In-unit laundry | Dishwasher

3 beds

1 bath

$2,895

House for rent

The best of Zumper, delivered

Be the first to hear about new listings matching your search.

Email
By clicking submit, I accept Zumper's Terms and Conditions, Privacy Policy, and Community Values.
241 N Main St - Photo 1 of 1

3d ago

House for rent in Monroe

SINGLE_FAMILY - Colonial - Monroe, NY

241 N Main St, Monroe, NY 10950

In-unit laundry | Outdoor space | Swimming pool

3 beds

1.5 baths

$3,600

House for rent

40 Felter Hill Rd - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

40 Felter Hill Rd, Monroe, NY 10950

In-unit laundry | Storage | Garage parking

3 beds

1.5 baths

$4,000

House for rent

Advertisement

Find sweet deals near Chester

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

9 Willard Pl - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

9 Willard Pl, Monroe, NY 10950

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$3,250

House for rent

12 Juniper Ln - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

12 Juniper Ln, Monroe, NY 10950

In-unit laundry | Garage parking | Hardwood floor

4 beds

3 baths

$3,700

House for rent

24A Cromwell Hill Rd - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Cottage - Monroe, NY

24A Cromwell Hill Rd, Monroe, NY 10950

Outdoor space | Carpet | Walk-in closets

1 bed

1 bath

$1,850

House for rent

112 Scott St - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

112 Scott St, Monroe, NY 10950

In-unit laundry | Furnished | Ceiling fan

3 beds

2 baths

$2,700

House for rent

5d+ ago

House for rent in Monroe

House for rent 2 beds 1 bath

8 Delano Grv, Monroe, NY 10950

In-unit laundry | Outdoor space | Hardwood floor

2 beds

1 bath

$2,100

House for rent

Available Apr 1

108 Highland Ave - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Colonial, Contemporary - Monroe, NY

108 Highland Ave, Monroe, NY 10950

In-unit laundry | Outdoor space | Storage

4 beds

1.5 baths

$3,500

House for rent

35 Peddler Hill Rd - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

35 Peddler Hill Rd, Monroe, NY 10950

In-unit laundry | Storage | Hardwood floor

3 beds

1 bath

$2,900

House for rent

157 State Route 17m - Photo 1 of 1

5d+ ago

House for rent in Harriman

SINGLE_FAMILY - Harriman, NY

157 State Route 17m, Harriman, NY 10926

In-unit laundry | Outdoor space | Storage

3 beds

1.5 baths

$3,350

$3,200

Price drop

House for rent

Advertisement
83 Lake Region Blvd - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

83 Lake Region Blvd, Monroe, NY 10950

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$3,850

$3,650

Price drop

House for rent

4 Millard Cir - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

4 Millard Cir, Monroe, NY 10950

In-unit laundry | Outdoor space | Garage parking

4 beds

3 baths

$5,200

House for rent

11 Peterson Rd - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Colonial - Monroe, NY

11 Peterson Rd, Monroe, NY 10950

Deck | Garage parking | Carpet

4 beds

2.5 baths

$4,600

House for rent

Listings within 10 miles
32 Oakwood Trl S - Photo 1 of 1

5d+ ago

House for rent in Monroe

32 Oakwood

32 Oakwood Trl S, Monroe, NY 10950

On-site laundry | Outdoor space | Fireplace

1 bed

1 bath

$1,575

House for rent

15 Stanton Trl - Photo 1 of 1

5d+ ago

House for rent in Monroe

15 Stanton

15 Stanton Trl, Monroe, NY 10950

Storage | Hardwood floor | Fireplace

3 beds

1 bath

$1,825

House for rent

36 Julie Ln - Photo 1 of 1

5d+ ago

House for rent in Greenwood Lake

1.5 Stories - Greenwood Lake, NJ

36 Julie Ln, Greenwood Lake, NJ 10926

In-unit laundry | Outdoor space | Storage

1 bed

1 bath

$2,250

House for rent

5d+ ago

House for rent in Monroe

3 Bedroom, 1 Bathroom House for Rent

4 Sunrise Trl, Monroe, NY 10950

In-unit laundry | Outdoor space | Hardwood floor

3 beds

1 bath

$2,300

House for rent

Available Mar 16

Showing 1 - 25 of 25 results
Home > House Rentals in Chester
Updated: April 14, 2026

Are you a rental professional?

Try our tenant screening, or post rental listings to Zumper, Craigslist Chester, and more.

Discover houses for rent in Chester, NY

🌇Available house rentals25 houses
💰Best rent deal492 Black Meadow Rd Apt A #Apt A
Popular amenities, ,
👚With laundry facilities
🍽With dishwasher
🚗With garage parking
❄️With air conditioning
🏠With photos