Escape to These Stunning Private Rentals, From Vineyard to Aspen

Lucía Torres · 2026-08-11

Looking for a late summer escape or planning ahead for a holiday sojourn? We have suggestions. From private estates on Martha's Vineyard to sun-drenched coastal villas in Sardinia and a ski-in/ski-out retreat in Aspen, our latest available leases are primed for your next getaway. Each property tells its own story, and we're here to help you find the one that fits your version of downtime. ### The Allure of Martha's Vineyard There's something about Martha's Vineyard that feels like stepping back in time—in the best way. The island's unhurried rhythm, salt-tinged air, and quiet beaches have a way of resetting your internal clock. Whether you're a first-timer or a returning regular, these Chilmark and West Tisbury properties offer the kind of privacy that's hard to come by these days. #### 18 Point Inner Way, Chilmark Represented by Valene Pires. Tucked away in one of the Vineyard's most coveted Up-Island enclaves, this Chilmark retreat offers the kind of privacy and authenticity that defines a true island escape. Set amid the natural beauty of the island's interior landscape, the property puts guests within easy reach of Chilmark's uncrowded beaches, farm stands, and unhurried coastal villages. It's the kind of place where you can leave your watch at home and let the tide set the schedule. #### 16 Shepherds Path, Chilmark Represented by Valene Pires. A refined island escape with interiors designed for long, unhurried summers, 16 Shepherds Path offers generous gathering spaces, carefully considered details, and the effortless flow between indoors and out. Whether hosting a large group or settling in for an extended stay, this property delivers a level of comfort and calm that's difficult to replicate. The design here isn't flashy—it's thoughtful, which is exactly what makes it feel so special. #### 41 Watcha Club Road, West Tisbury Represented by Paul Pertile. Secluded within a quiet West Tisbury setting in the center of the island, this four-bedroom coastal home pairs laid-back beach-house ease with amenities that genuinely deliver. A private beach and swimming pool define the outdoor experience, while the home's relaxed, sunwashed aesthetic carries the island's spirit through every room. For those who want waterfront access without the crowds, Watcha Club Road is the answer. #### 30 Pierce Lane, Edgartown Represented by Paul Pertile. When a rental is built for a group, it should feel that way from the moment you arrive. This six-bedroom Edgartown estate is designed precisely for the kind of summer gathering that needs room to breathe, featuring multiple sitting rooms, a screened-in porch, a swimming pool, and a pool house complete with its own kitchen, bedroom, pull-out sofa, and full bath. Below the main level, an entertainment floor with shuffleboard, a television lounge, and an electric fireplace ensures that the evening carries on long after dinner. ### City Escapes: Brooklyn's Williamsburg Not every rental story is a retreat from the city; sometimes the city is the destination. This stylish Williamsburg residence puts guests at the center of one of Brooklyn's most dynamic neighborhoods, with world-class dining, independent boutiques, and waterfront parks all within reach. Polished interiors and a thoughtful layout make it as well suited to a longer stay as a short one. If you're craving the energy of New York without the chaos of midtown, this is your sweet spot. ### Aspen's Alpine Masterpiece At the end of a private road in Aspen's exclusive Five Trees neighborhood, 170 Falcon Road is among the rarest offerings in Colorado mountain rentals: a true ski-in/ski-out estate with sweeping views across the Roaring Fork Valley. Set on 1.4 acres, the nearly 9,000-square-foot residence pairs timeless mountain architecture—stone, timber, dramatic proportion—with finishes that feel genuinely refined rather than merely expensive. Five en-suite bedrooms include a main-level primary suite, while the chef's kitchen and great room centered on a floor-to-ceiling stone fireplace become natural gathering points for any group. Outside, an alpine retreat awaits: a spa, a waterfall feature, and multiple entertaining terraces. A large gym with cold plunge rounds out the amenities. Whether you're here for powder days or summer hikes, this home delivers on every front. ### Why These Rentals Stand Out Here's the thing about luxury rentals—it's not just about square footage or fancy finishes. It's about how a place makes you feel. These properties were chosen because they offer something genuine: - Privacy that lets you actually relax - Locations that put you close to the best of each destination - Amenities that go beyond the basics (think private beaches, cold plunges, and pool houses) - Interiors that feel lived-in and loved, not staged ### Planning Your Escape Whether you're dreaming of a Vineyard summer, a Brooklyn city break, or an Aspen winter, the key is to book early. The best properties go quickly, especially for peak seasons. And if you're flexible with dates, you might just find a hidden gem that fits your schedule perfectly. Happy travels—we'll see you out there.