11 Dreamy Winter Escapes

11 Dreamy Winter Escapes

‘Tis the season to escape. From hibernation-worthy mountain chalets to coastal retreats where snowbirds can soak up the vitamin D, explore luxe rental listings where you can satisfy your winter wanderlust.

New York

108 Montauk Highway, East Hampton

Despite being one of the world’s most famous summertime destinations, East Hampton makes for a much quieter and more relaxing winter getaway. Enjoy the quiet beaches and quaint Main Streets in peace, then retreat to this East Hampton Village colonial estate. Set on a private acre, the property boasts five bedrooms and bathrooms, where you can spend the season curling up with books by the fire or comfortably entertaining as many as 10 guests. John Caulfield holds the listing.

22 Oak Lane, Amagansett

Close to the Jitney stop, this fully stocked two-bedroom, two-bathroom cottage has the charming character of its original details and the comfort of modern amenities — including a detached space you can use as an office. After a day of remote work or exploring the surrounding trails, come back to soak in your tub or cozy up on the couch with a movie. Just bring your bags. John Caulfield holds the listing.


49880 Rancho San Felipe, La Quinta

Escape to this entertainer’s oasis in the desert. The private backyard features a lagoon-style pool, including a swim-up bar, and spa. Enjoy outdoor dining on the covered patio, complete with an outdoor kitchen, fireplace, television and ping pong table. Inside you can play pool, host game nights and lounge in California casual style. Four bedrooms comfortably sleep eight. Loran Arvizu holds the listing. 

1172 Linda Flora Drive, Holmby Hills

Wait out the winter months in a state-of-the-art smart home in Lower Bel Air’s most coveted neighborhood. Beautifully designed and furnished, the spacious floor plan includes double-height ceilings and walls of glass that make the most of the natural light and panoramic canyon and city views. Prepared to cater to all lifestyles, the home also includes a gourmet kitchen, five-bedroom suites and a backyard made for luxury indoor-outdoor living. Natalie Codoch holds the listing. 

2400 N Milo Drive, Palm Springs

A classic mid-century, this desert paradise wows with its views of the valley, modern yet period-appropriate furnishings and pool. The open floor plan is ideal for entertaining, as is the formal sitting room with a fireplace and outdoor pool. Work from “home” in the den/bonus room. When you need to get away from your getaway, you’re only minutes from downtown shopping and restaurants. Michelle Knutson and Paul Lester hold the listing.

1881 S Araby Drive #15, Palm Springs

Take a month to rest and reconnect at this single-bedroom pied-à-terre in the CoCo Cabana community, surrounded by park-inspired grounds, endless mountain views and palm trees. Enjoy designated parking as well as access to the community pool, spa and two tennis courts. Close to Downtown Palm Springs, you can be at favorite local spots in a matter of minutes, including Ace Hotel. Michelle Knutson and Paul Lester hold the listing.

2086 S Barona Road, Palm Springs

The Dresslar Farm Estate is an artist’s jewel box that offers luxurious resort-inspired living. Designed for private relaxation and entertaining, the grounds feature a pool, spa, fire pit and fully outfitted outdoor kitchen. Panoramic views of the surrounding Jacinto Mountains and colorful accents pop against the clean white background. The freshly remodeled kitchen features new Viking appliances. Michelle Knutson and Paul Lester hold the listing. 

1765 Royal Palm Court, Palm Springs

Your turnkey desert oasis awaits. Outfitted with furnishings, cookware, linens, laundry and a built-in sound system, this four-bedroom architectural home sits at the end of a quiet cul-de-sac only blocks from Palm Canyon Drive. Spend your days sunbathing around the pool and spa. At night, gather friends for a barbecue and roast marshmallows around the fire pit. Michelle Knutson and Paul Lester hold the listing.


6 Avenue des Amiraux, Estérel, Québec

This home designed by Roger D’Astous (who also designed Montreal’s Olympic Village towers) has been lovingly dubbed the “Icon” of Estérel. The main living area is both big enough to host a party and cozy enough to enjoy an intimate evening by the fire. The six bedrooms comfortably accommodate 20. The location makes it easy to ski at the nearby resorts and snowmobile on surrounding trails before coming back for an evening of soaking in the hot tub or watching a movie in your home theater. No other home compares in size and amenities. Joshua Jagermann holds the listing.


501 W Hopkins Avenue, Aspen

Only blocks from town, this Aspen estate features striking views of Shadow Mountain, three elevator-serviced levels and six bedrooms that can host more than a dozen guests. After a day on the powdery slopes, come home to resort-level luxury. Warm up in the private outdoor hot tub, entertain in an expansive living area and curl up in front of any of the four grand fireplaces. With a downstairs game room and family-friendly home theater, this house sets the stage for the ultimate Aspen vacation. The listing is held by Lisa Hatem


La Palmeraie 1, Bahamas

A night in this spectacular beachside estate can run anywhere from $8,000 to $15,000. One look, and it’s no wonder why. La Palmeraie 1 boasts every amenity you could ever hope for — especially when the weather at home turns gray and cold: a private sun deck, heated pool, full fitness center and steam room, on top of turquoise ocean views. Danny Lowe holds the listing.

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