High-end rentals offer a unique blend of flexibility and luxury, pairing the ease of temporary living with the comforts of a thoughtfully designed home. These residences go beyond standard leases, delivering elevated architecture, expertly arranged interiors, and access to nature or vibrant coastal communities. Whether perched in the hills of Litchfield County, overlooking a tranquil pond in Scarsdale, or set along the shoreline in Old Saybrook, each property offers its own refined take on retreat. For those seeking style without permanence, these rentals are a rare opportunity to experience exceptional living on your own terms.
3,082 Sqft | $25,000/mo
Set atop one of Kent’s most coveted ridgelines, this refined modern escape offers panoramic views of the Catskills and rolling Litchfield Hills. The architecture invites light into every corner, with expansive windows framing the horizon and vaulted cedar ceilings adding warmth to the airy interiors. A heated gunite pool and bluestone terrace extend the living space outdoors, where nearly seven acres of privacy surround you. Inside, three levels of thoughtfully designed living blend quiet luxury with seamless indoor-outdoor flow.
9A Lincoln Woods, Purchase, NY
10,378 Sqft | $20,000/mo
Tucked at the end of a serene cul‑de‑sac in Purchase, this distinguished colonial redefines elegant rental living. Designed by Chris Demetriades and spanning nearly 10,400 square feet on almost two landscaped acres, the home blends soaring ceilings, abundant natural light, and a grand foyer that welcomes you in. With six bedrooms, each with its own bath, a heated pool, walk‑out lower level with gym and recreation space, and a flexible first‑floor guest suite, this residence offers refined comfort and versatility. Offered on a flexible lease, it’s a rare chance to enjoy turnkey luxury in one of Westchester’s most coveted neighborhoods.
5,029 Sqft | $10,000/mo
On nearly 14 private acres in South Kent, this modern hillside home captures sweeping western views that extend to the distant Catskills. A dramatic steel and glass staircase anchors the open living space, where soaring ceilings and full-height windows create a seamless connection to nature. The main level includes a warm den, guest suite, and access to a covered porch and heated gunite pool. Upstairs, the primary suite is joined by two more bedrooms and a top-floor loft with kitchenette, offering space for guests or quiet retreat.
2,400 Sqft | $6,800/mo
Surrounded by four acres of peaceful Berkshire landscape, this architect-designed home offers a quiet connection to nature and comfort. The main residence features vaulted ceilings, an open layout, and natural finishes that feel both grounded and refined. A separate heated barn with a sleeping loft and full bath adds flexibility for guests, creative work, or extended stays. Stone patios, perennial gardens, and access to shared tennis courts, trails, and a nearby pond complete the experience of relaxed, seasonal living.
29 West Shore Drive, Old Saybrook, CT
2,500 Sqft | $9,500/mo
Overlooking the water within the Cornfield Point Association, this four-bedroom colonial offers direct waterfront living with dramatic sunset views from the spacious living room. Fully furnished for the academic term starting October 1, the home includes a cozy fireplace, main-level laundry, and an attached one-car garage. A large patio extends outdoor living space beside the oversized waterfront lot. Located steps from restaurants, shopping, the train station, and I‑95, this home blends ease and elegance for a seasonal retreat.
Explore more homes for rent here.
