Private Estates for Rent: From Martha's 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, our latest available leases are primed for your next getaway. Whether you crave salty ocean air, mountain solitude, or the electric hum of the city, these homes have one thing in common: they're ready when you are. ### Martha's Vineyard, Massachusetts The Vineyard has a way of slowing time down. It's not just the ferries or the sandy roads; it's the rhythm of the island itself. These three properties capture that spirit beautifully, each offering a different take on the classic island summer. #### 18 Point Inner Way, Chilmark 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 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 you're 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 doesn't shout; it whispers, which is exactly what a good summer house should do. #### 41 Watcha Club Road, West Tisbury 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 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. Think 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 the evening carries on long after dinner. ### New York, New York Not every rental story is a retreat from the city; sometimes the city is the destination. #### 286 Manhattan Avenue, Williamsburg 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 want to wake up and walk straight into the best coffee, vintage shopping, and skyline views the borough has to offer, this is your home base. ### Aspen, Colorado 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 a cold plunge rounds out the amenities. > The best rentals aren't just places to sleep. They're places that change how you spend your time. ### What to Consider Before You Book Before you commit to a premium rental, keep these things in mind: - **Seasonality matters.** Late summer on the Vineyard is golden, but Aspen truly shines in winter. Match the property to the season you're chasing. - **Group dynamics.** If you're traveling with extended family or friends, look for properties with multiple sitting areas and separate sleeping quarters. Privacy is a luxury too. - **Location is everything.** Decide whether you want walkable access to town or complete seclusion. Both are valid; just know which one you're signing up for. - **Amenities that matter.** A pool, a gym, or a game room can make or break a longer stay. Prioritize what your group actually uses. Each of these properties is represented by a dedicated agent who knows the local market inside and out. Whether you're dreaming of an island summer or a mountain winter, the right door is waiting to be opened.