Houses for Rent in Roxbury, CT

Experience a stylish retreat in this unique vaulted pool house featuring a king bedroom plus a flexible trundle room. Spanning 900 sq ft, this space is equipped with a chef's kitchen, a cozy fireplace, and covered BBQ area ideal for gatherings. Enjoy stunning views from the deck overlooking the pool. Seasonal and annual rental options are available, with discounts for longer stays. Perfect as a standalone or with the main house for larger accommodations.

Immerse in charm with a restored 3-bed, 3.5-bath Victorian cottage featuring lush gardens and a sparkling pool/spa. Enjoy the scenic beauty ideal for walking or biking, surrounded by quaint stone terraces. The interior offers a cozy fireplace and modern amenities, merging timeless elegance with contemporary comfort. Experience a serene retreat cherished by artists and executives alike.

Discover tranquility in this renovated 4-bedroom Colonial home nestled by the Shepaug River. Offering 2,080 sq ft, it features a year-round spa pool, open floor plan, and elegant granite terrace. Enjoy the warmth of a wood-burning fireplace and the convenience of a basement and garage parking, all moments away from Steep Rock's trails. Available for seasonal and annual rent.

This expansive 6-bed, 3.5-bath colonial home offers a serene lifestyle on a scenic road in Roxbury. Set on 3 acres, this 2,716 sq ft home features 4 wood-burning fireplaces, a heated pool, and outdoor play areas. Enjoy proximity to a stunning land preserve. Flexible rental terms cater to summer and off-season stays, making it an ideal retreat year-round.

Experience exquisite living in this St. Barth's-style 4-bed, 4-bath home featuring 2,396 sq ft of elegance. Nestled in a serene hilltop neighborhood, enjoy high ceilings, exceptional interior design, and two wood-burning fireplaces. Relax by the heated pool or explore generous rental options, including flexible summer and off-season rates. Ideal for those seeking comfort and style in a picturesque setting.

Tucked amidst wildflower clearings and granite outcroppings, this 4,000 sq ft Mid-Century Modern home offers a serene retreat. Cathedral ceilings and skylights create a light-filled atmosphere, while the primary suite features a spa-like bath and ample storage. An expansive patio allows for outdoor enjoyment, enhanced by artistic sculptures and stonework. Embrace the tranquility of this unique architectural sanctuary, perfectly blending privacy with the charm of nature.

Experience serene living in this delightful 4-bedroom, 2.5-bath Colonial set on 4 pastoral acres. The expansive 3,089 sq. ft. home boasts a vaulted-ceiling Great Room, a cozy formal living room with a wood-burning fireplace, and an eat-in country kitchen. Enjoy outdoor leisure in the beautiful terrace and magnificent gunite pool, along with nearby tennis courts, local markets, and scenic trails. This idyllic retreat blends charm and comfort in a picturesque setting.

Experience mid-century modern living in this stunning single-level home featuring 3 bedrooms and 3.5 bathrooms across 3,236 square feet. Floor-to-ceiling windows illuminate the versatile layout, including a sunroom, formal living room with fireplace, and updated kitchen with stainless steel appliances. Enjoy outdoor relaxation by the granite patio and gorgeous inground pool, while the lush landscaped grounds provide a private escape. The property also includes a two-bay garage with a studio.

Experience tranquil living in this charming barn-style home set on 15.27 acres, featuring 4 bedrooms and 2.5 baths. The open floor plan is enhanced by exposed timber and a stunning double-sided stone fireplace. French doors lead to a rear patio overlooking an inviting in-ground pool and barrel sauna, perfect for summer escapes. Just 90 minutes from NYC, this spacious 3,026 sq. ft. residence offers a remarkable short-term rental opportunity from September to May.

Nestled in Roxbury's serene landscape, this 4-bed, 2.5-bath Cape Cod home offers breathtaking hilltop views. Enjoy relaxing or dining on the flagstone terrace, a cozy wood-burning fireplace, and a master suite with a private balcony. With amenities like ping pong, a trampoline, croquet, and more, this art-filled retreat promises a perfect blend of comfort and leisure. Available for seasonal or long-term stays.

Nestled on a scenic country road, this sprawling 6-bed, 3.5-bath Colonial offers 4,251 sq. ft. of luxury. Featuring a heated pool, child's play gym, and vast outdoor space, it's ideal for relaxation and recreation. Close to Roxbury's cultural gems and just two hours from NYC, enjoy a vibrant arts scene, outdoor adventures, and world-class dining. Perfect for seasonal or annual rental.