There’s a lot to be said for living like a local. But what about when those locals are among the jet set? When homeowners are off gallivanting and not in one place all the time, the luck is all yours since many of them are offering up their second, third and fourth homes for vacationers willing to splurge on whole-home rentals.
Whether you’re traveling with your brood, a group of friends or just want extra elbow room, the homes of Madeline Hotel & Residences offer up a chic retreat after a day on the slopes in Telluride. From a four-bedroom penthouse with 3,900 square feet nestled in the top floor for beautiful mountain views to a two-bedroom on the same floor with a full kitchen, the multiuse Madeline means those renting a hotel room are in the same complex as those renting a more luxe home away from home. It’s all part of Auberge Resorts’ collection that also includes sunny Los Cabos, Mexico (Chileno Bay Resort & Residences) and fun Fort Lauderdale (Auberge Beach), among others.
“Cottages” take on a whole new meaning in Kennebunkport, Maine, home to former president George H.W. Bush’s Camp David. The same stunning seaside that so captivated the press during his time in office and that of his son in this sleepy town comes alive in summer like Dorothy waking up in Oz. KPT Luxury Properties specializes in luxury home rentals here, mostly on the water, and all near one of New England’s best beaches. Accommodations include high-end linens, housekeeping, concierge service, in-home dining (upon request), yacht charters, fishing tours and more.

Kennebunkport, Maine © Enrico Della Pietra | Dreamstime.com
Who knew a farm could be luxurious? The dining room that sits up to 24 means you can even invite a few friends over to admire the 3,200-log cabin and stunning views overlooking the swimming pond here. There’s even a large master bedroom with a king-sized bed, Jacuzzi tub, a library, full bar, two dishwashers (for that dinner!) and a fire pit and horseshoes outside. Nestled in between Mount Washington and the Appalacian Trail, there’s plenty to do outside, or just admire the views of Mt. Moosilauke in Bath, New Hampshire. The Lodge is part of 265-acre farm that raises cattle, sheep, pigs and chickens.
Less than 5 percent of homeowners who apply are accepted for Luxury Retreats, with the site’s 50-person inspection staff personally reviewing all applicants’ properties with a 100-point luxury inspection checklist. The site splits properties into categories like resort living (pinpointing 81 homes on Hawai’i’s Big Island); Natural Beauty (91 villas on Riviera Maya); and Active Vacationers (47 villas at Lake Tahoe).
Though it may be part of the AccorHotels’ family (with other luxury brands like Sofitel and Fairmont Raffles), Onefinestay is about much more than a hotel stay — it’s like living like a well-to-do local. More than 2,500 homes are listed in London, Paris, Rome, New York, Los Angeles and Miami (there are some other smaller markets), and there’s a service component even before “checking in.” Travel advisors review each potential guest’s preferences and advise on which homes are best. Only 1 in 10 homeowners are approved to be listed, and there’s a 24/7 Guest Services team.
Want to rent your own massive, seven-bedroom, ski-in/ski-out luxury home in Utah? Or a secluded eight-bedroom villa in St. John overlooking the ocean? Villas of Distinction is the place to look. While bargains on wallet-busting stays like Le Bleu in Anguilla — which sleeps 20 as you may have seen on The Bachelor —probably aren’t the primary concern in this price point (starting at $7,500 a night), the site does have specials from time to time. The tiered package for New Year’s celebrations in St. John at Eco Serendib included reduced rates and a meet and greet, in-person concierge and mid-week housekeeper refreshing.
Read This Next
5 Family-Friendly Museums in Charleston
Destinations / North America
Aug 22, 2024#WhereverFamily
Insta FeedHotels
Oct 28, 2026Get “Wrapped in The Moment” With Fairmont Hotels & Resorts This Holiday Season
Fairmont Hotels & Resorts properties across the globe go above and beyond this holiday season to make it the most memorable one yet for family travelers. Encouraging families to slow down, reconnect with one another and savor this joyous time of year, Fairmont presents “Wrapped in the Moment.”
Sponsored Content
Best of Both Worlds
Enjoy the best of both worlds when you fly with TAP Air Portugal thanks to the Portugal Stopover program. With the program, TAP passengers, whether traveling for business, leisure or both, can stop in Portugal for up to 10 days at no additional airfare on the way to their final destination. What does this mean for travelers wishing to explore by both land and sea? It means after flying to Portugal with TAP and experiencing the country in an entirely new way, travelers can then embark on scenic river and ocean cruises from Portugal’s port cities, or fly with TAP to another European destination.
Destinations / North America
Oct 28, 2026A Quick Guide on Visiting Arches National Park with Family
Arches National Park in southern Utah is an experience in nature like few others. Dramatic red cliffs tower above a desert landscape studded by fantastic rock formations. You can drive, hike or amble among them; each new perspective begs for a photo. Kids love this unreal landscape, which seems the setting for an epic fantasy movie.
Destinations / North America
Oct 28, 2026Lights, Eagles and Skiing Await in Coeur d’Alene, Idaho, This Winter
Coeur d’Alene, Idaho, may be most family travelers’ idea of a summer destination, but come winter, this North Idaho spot transforms into something entirely different. Think more than one million holiday lights reflected across the water, mountains topped with snow for skiing, and migrating bald eagles along the shoreline and on mountainsides.
Sponsored Content
GET TO KNOW TAP FORBIZ
Unlock flexible, refined business travel with TAP Air Portugal’s program, TAP FORBIZ. Developed for small, medium and large Companies, with options for corporate events, TAP FORBIZ offers exclusive advantages adapted to each type of business.
Destinations / Europe
Oct 27, 2026This German Region is a Can’t-Miss for Autmn
Germany is an obvious choice if you want to visit the country’s world-famous Christmas markets. But if you haven’t considered it for a fall travel destination, you are missing out on some pretty amazing experiences to share with your family. The only problem is, how do you choose which region to visit? We’ll help narrow it down for you: Bavaria is a can’t-miss region.
ShareThis