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Houses for Rent in Chester, NY

Average rent

$3,100

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3607 Whispering Hills Drive - Photo 1 of 1

3d ago

Townhouse for rent in Chester

3607 Whispering Hills Drive, Chester, NY 10918

In-unit laundry | Outdoor space | Storage

2 beds

1 bath

$2,450

House for rent

Bright & Stylish Townhome with Resort-Style Amenities

This charming 2-bedroom, 1.5-bathroom townhome features a beautifully renovated kitchen with stainless steel appliances and a dedicated laundry room. Natural light floods the space, enhanced by a cathedral ceiling and skylight. Enjoy the convenience of a two-car detached garage and access to fantastic community amenities, including pools, tennis courts, and a fitness center. Experience a vibrant lifestyle in this thoughtfully updated home!

52 Surrey Road - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Ranch - Chester, NY

52 Surrey Road, Chester, NY 10918

Outdoor space | Garage parking | Fireplace

4 beds

2 baths

$3,750

$3,300

Price drop

House for rent

Cozy Family Retreat with Spacious Backyard & Garage

Fall in love with this beautifully renovated 4-bedroom, 2-bathroom home spanning 1,780 sq ft. The flexible layout features shiny stainless steel appliances and a cozy fireplace. Enjoy summer evenings in the spacious backyard, perfect for barbecues and stargazing. The unique 3-car detached garage offers room for all your adventures. Located in a friendly neighborhood, with parks and local shops within walking distance, this home combines comfort, convenience, and community charm.

948 Craigville Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

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.

2507 Whispering Hls - Photo 1 of 1

5d+ ago

House for rent in Chester

Single Family Residence, Traditional - Chester, NY

2507 Whispering Hls, Chester, NY 10918

In-unit laundry | Outdoor space | Garage parking

2 beds

1 bath

$2,300

House for rent

Modern 2-Bed Retreat with Pool & Tennis Court

Experience comfort in this cozy 2-bedroom, 1.5-bath home featuring a welcoming fireplace and skylight. Enjoy modern conveniences with a new furnace and refrigerator, in-unit laundry, and a private fenced patio. Additional perks include a refreshing swimming pool, children's playground, and nearby hiking trails. With a 2-car garage and convenient access to outdoor activities, this rental offers an ideal lifestyle for relaxation and fun in the great outdoors.

25 Trotting Drive - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Ranch - Chester, NY

25 Trotting Drive, Chester, NY 10918

In-unit laundry | Outdoor space | Garage parking

4 beds

1 bath

$3,000

House for rent

Spacious Family Home in a Peaceful Neighborhood

This charming 4-bedroom, 1.5-bath home offers 1,800 sqft of living space in a serene Chester neighborhood. Ideal for comfortable living, it features a cozy fireplace, in-unit laundry, and garage parking. Enjoy the convenience of local shopping and schools nearby, with trash collection and lawn maintenance included. With room for pets, this rental is perfect for those seeking an inviting space in a desirable community.

3404 Whispering Hls Unit 44260 #44260 - Photo 1 of 1

5d+ ago

Townhouse for rent in Chester

SINGLE_FAMILY - Chester, NY

3404 Whispering Hls Unit 44260 #44260, Chester, NY 10918

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$2,800

House for rent

Charming Townhouse with Pool & Inviting Patio

This spacious 3-bedroom, 2.5-bath townhouse features an open floor plan with laminate floors and a cozy fireplace. The modern kitchen is equipped with stainless steel appliances and offers ample counter space. Upstairs, a master suite ensures privacy, while a private patio is perfect for relaxation. Enjoy community amenities like a sparkling pool, tennis court, and playground. With plenty of storage options and a commuter-friendly location, this home combines comfort and convenience beautifully.

Nearby rental good for eco-living

Nearby rental good for social life

22 Lake Avenue - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

22 Lake Avenue, Monroe, NY 10950

Outdoor space | Air conditioning | Hardwood floor

3 beds

1 bath

$2,300

House for rent

24 Lake Avenue - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Colonial - Monroe, NY

24 Lake Avenue, Monroe, NY 10950

On-site laundry | Outdoor space | Garage parking

4 beds

2 baths

$3,100

House for rent

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27 Sunny Lane - Photo 1 of 1

5d+ ago

House for rent in Highland Mills

27 Sunny Lane, Highland Mills, NY 10930

4 beds

1 bath

$2,600

House for rent

36 Swezey Place - Photo 1 of 1

5d+ ago

House for rent in Monroe

36 Swezey Place, Monroe, NY 10950

In-unit laundry

3 beds

1 bath

$3,200

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.

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 bath

$3,500

House for rent

16 Fitzgerald Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Monroe

16 Fitzgerald Ct, Monroe, NY 10950

In-unit laundry | Outdoor space | Air conditioning

3 beds

1 bath

$2,800

House for rent

315 Arcadia Rd - Photo 1 of 1

5d+ ago

House for rent in Goshen

Single Family Residence, Colonial - Goshen, NY

315 Arcadia Rd, Goshen, NY 10924

In-unit laundry | Storage | High ceilings

2 beds

1 bath

$3,000

House for rent

16 Jmd Dr - Photo 1 of 1

5d+ ago

House for rent in Monroe

Single Family Residence, Mini Estate - Monroe, NY

16 Jmd Dr, Monroe, NY 10950

In-unit laundry | Ceiling fan | Dishwasher

2 beds

2 baths

$2,600

House for rent

53 Barr Ln #D1 - Photo 1 of 1

5d+ ago

Townhouse for rent in Monroe

Condominium - Monroe, NY

53 Barr Ln #D1, Monroe, NY 10950

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$3,400

House for rent

Listings within 10 miles
7 Herbst Drive - Photo 1 of 1

2d ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

7 Herbst Drive, Monroe, NY 10950

Outdoor space

3 beds

1 bath

$2,500

House for rent

172 County Road 105 - Photo 1 of 1

2d ago

House for rent in Highland Mills

172 County Road 105, Highland Mills, NY 10930

In-unit laundry

3 beds

1 bath

$2,700

House for rent

12 Revere Road - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Ranch - Monroe, NY

12 Revere Road, Monroe, NY 10950

Dishwasher

3 beds

3 baths

$2,900

House for rent

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10 Murray Avenue - Photo 1 of 1

5d+ ago

House for rent in Goshen

SINGLE_FAMILY - Colonial - Goshen, NY

10 Murray Avenue, Goshen, NY 10924

In-unit laundry | Outdoor space | Storage

3 beds

1 bath

$2,600

House for rent

25 Emerald Trail - Photo 1 of 1

5d+ ago

House for rent in Monroe

SINGLE_FAMILY - Bungalow - Monroe, NY

25 Emerald Trail, Monroe, NY 10950

2 beds

1 bath

$2,400

$2,300

Price drop

House for rent

43 Bruen Pl - Photo 1 of 1

5d+ ago

House for rent in Goshen

SINGLE_FAMILY - Other - Goshen, NY

43 Bruen Pl, Goshen, NY 10924

In-unit laundry | Outdoor space | Storage

2 beds

2 baths

$2,800

House for rent

23 Prospect Avenue #1 - Photo 1 of 1

5d+ ago

Townhouse for rent in Goshen

APARTMENT - Goshen, NY

23 Prospect Avenue #1, Goshen, NY 10924

In-unit laundry | Outdoor space | Storage

2 beds

2 baths

$3,500

$3,200

Price drop

House for rent

9 Upper Hillman Road - Photo 1 of 1

5d+ ago

House for rent in Warwick

SINGLE_FAMILY - Ranch - Warwick, NY

9 Upper Hillman Road, Warwick, NY 10990

In-unit laundry | Outdoor space | Storage

2 beds

1 bath

$2,300

House for rent

24 Northgate - Photo 1 of 1

5d+ ago

House for rent in Goshen

Single Family Residence, Colonial - Goshen, NY

24 Northgate, Goshen, NY 10924

In-unit laundry | Outdoor space | Storage

4 beds

3 baths

$6,000

House for rent

113 Barr Ln - Photo 1 of 1

5d+ ago

Townhouse for rent in Monroe

113 Barr Ln, Monroe, NY 10950

In-unit laundry | Outdoor space | Garage parking

3 beds

3 baths

$3,600

House for rent

Showing 1 - 25 of 25 results
Home > House Rentals in Chester
Updated: November 29, 2025

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Discover houses for rent in Chester, NY

🌇Available house rentals25 houses
💰Best rent deal22 Lake Avenue
🍃With outdoor space
Popular amenities, ,
🍽With dishwasher
🚗With garage parking
❄️With air conditioning
🏠With photos