From Martha's Vineyard to Aspen: The Season's Most Coveted Stays

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, our latest available leases are primed for your next getaway. But we're not just stopping at the coast—we've also found a gem in the mountains that'll make you want to book a winter trip before the leaves even turn. ### Why These Rentals Stand Out What makes a rental truly memorable? It's not just the square footage or the fancy finishes—it's how a place makes you feel the moment you walk in. The properties below share a few common threads: privacy, thoughtful design, and locations that put you right where you want to be, whether that's steps from the sand or slopes away from the lift. ### Martha's Vineyard, Massachusetts **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 actually hear yourself think—a rare commodity these days. **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 about showing off; it's about creating a backdrop for real life. **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. ### New York, New York **286 Manhattan Avenue, Williamsburg** — Represented by Maurice Singer 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 looking to feel the pulse of the city without sacrificing comfort, this is your spot. ### Aspen, Colorado **170 Falcon Road** — Represented by Heather Sinclair 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. ### Planning Your Booking Here's a quick breakdown of what to consider when booking any of these properties: - **Lead time**: Peak season rentals in Martha's Vineyard and Aspen often book 6–12 months out, so start early. - **Group size**: Some of these homes are better suited for large gatherings (30 Pierce Lane, 170 Falcon Road) while others are perfect for intimate getaways. - **Seasonality**: The Vineyard shines in summer, but Aspen is a year-round destination with skiing in winter and hiking in summer. - **Budget**: Prices vary widely based on season and property size—expect to pay a premium for ski-in/ski-out access or private beachfront. As one seasoned traveler once told us, "The best rentals aren't just places to sleep—they're settings for the stories you'll tell for years." We couldn't agree more. Whether you're dreaming of salt air and sand between your toes or crisp mountain mornings and powder days, these properties offer something increasingly rare: a place that feels like yours, even if only for a week or two.