Houses for Rent in Chester, NY

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.

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.

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!

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.

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.

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.

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.