From taking turns through fresh powder on a private snowboard lesson to reserving desirable seats at a concert, Aspen is built on moments you won’t forget. After time on the slopes, the scene shifts to lively après-outdoor activities and dining rooms where chefs craft multi-course tastings and seasonal dishes. Wherever your explorations take you, returning to the elegance of an Aspen Vacation Rentals property is a relaxing way to end the day.
Aspen Snowmass Adventures
Aspen Vacation Rentals properties place you at the heart of the outdoors, with no better base than a four-season mountain resort. For exclusive things to do in Aspen in winter, the Aspen Mountain Powder tour tops the list, giving skiers and snowboarders access to untouched backcountry snow. You start with a gondola ride to the summit, where a reserved snowcat awaits to take you farther into the mountains and onto slopes blanketed by fresh snowfall. Later, you’ll stop at a wood-stove-heated cabin for a gourmet lunch before heading back out to slice through the powder.
If you’re new to the slopes or looking to sharpen your skills, the resort turns learning into a luxury with its private ski and snowboard lessons. These one-on-one sessions are designed just for you, with priority lift access and the rare choice of which of the four mountains that make up Aspen Snowmass becomes your classroom. A personal coach glides alongside, guiding you to runs that fit your pace — whether it’s linking your first turns on gentle trails or carving smoother lines down steeper pitches. By the end, you’ve not only gained confidence but experienced the slopes the way only discerning travelers will know.
Summer brings just as much allure as winter, with some of the most exciting things to do in Aspen once the snow melts. Start the morning with a cup of coffee on the patio of your Aspen Vacation Rentals home, looking out at mountains vistas. When you’re ready to get moving, pull on your gear and head to the resort for a private mountain-biking lesson. Maybe you’re after the rush of a downhill ride or prefer the steady pace of cross-country routes — either way, your coach keeps rhythm, offering pointers along the way. You’ll wind through Snowmass Bike Park’s trails, with jumps, turns and paths built for every kind of rider.
For more thrills, the resort’s Canopy Run Zipline Tour at Lost Forest offers a different way to see Aspen’s outdoors. Your day begins with a gondola ride, followed by the rush of an alpine coaster and a climbing wall that gets your adrenaline going. Then expert guides lead you on a three-hour journey through the treetops, where you zip high above the forest for a bird’s-eye-view you can’t see any other way.
Après-Ski Scenes Nearby
Depending on your choice, an Aspen Vacation Rentals home can place you just a block from The Little Nell, where The Nest — operated by Element 47 — offers a stylish outdoor patio made for après-ski lounging. Firepits glow as you sink into plush seating, the perfect setting to sip cocktails and unwind in true Aspen fashion.
If you’re after a refined scene, the Caribou Club is one of Aspen’s most prestigious nightspots. It’s so exclusive you need a membership to get in, whether it’s for the week or the year — which, honestly, is a pretty good reason to come back. Inside, the food is next level. Chefs mix global flavors with local ingredients into dishes that taste even better than they look. When the plates are cleared, the DJ takes over and suddenly the place is all about dancing into the night.
At Aspen Highlands, you’ll find Cloud Nine Bistro. Around midday, this spot leans into the party scene with Champagne bottles popping and glasses lifted for toasts. You can warm up with live music and dancing or linger at the table over bubbling fondue filling the space with its aroma, and yes, caviar is on the menu too. The mix of time on the mountain and socializing at the bistro makes the evening back at your Aspen Vacation Rentals home all the more comforting, with a fire and a blanket to recharge for whatever tomorrow brings.
Refined Dining Experiences
In Aspen, luxury doesn’t end with outdoor adventures or even the comfort of your rental home — you can taste it too. Bosq, the town’s MICHELIN-starred restaurant, builds its menus around the season, offering five-course and chef’s-tasting menus. The team works with nearby farmers, ranchers and foragers, turning what comes through the door into inventive dishes. Past plates have included grilled rabbit with foraged leaves or harissa-spiced bison tartare, dishes that make you close your eyes and savor every bite.
For dinner with a view, Catch Steak Aspen’s outdoor terrace looks straight at Aspen Mountain, a backdrop that turns feasting on aged steak or Japanese wagyu into an alpine experience. Indoors, the atmosphere feels warm and inviting, with wood beams overhead and soft lighting. If you’re with a group and want something more private, the Red Room serves as a hideaway with its own private entrance, velvet walls and a marble bar.
Japanese dining reaches its peak at Matsuhisa, where chef Nobu Matsuhisa presents an omakase tasting menu that changes with the season. Courses move from signature dishes to new creations, each one designed to surprise, especially when paired with premium sake. For smaller groups, the Nobu Room offers a more intimate setting that can be reserved.
Indulgent Spa Treatments
While staying in the cozy mountain setting of an Aspen Vacation Rentals home, soaking in a bubbling hot tub might feel like all the relaxation you need. When you want more than that, a short drive brings you to Yarrow, an Auberge Spa at Hotel Jerome. Curated therapies use organic botanicals and natural elements from the Rockies. Each visit comes with thoughtful touches that leave you feeling restored, like complimentary tea and a steam shower.
After a day in the high-altitude air, few things are as soothing as an appointment with Aspen Luxe Med Spa. You can choose from gua sha, cupping or a chemical peel — treatments that smooth out the wear and tear of being outside all day. The setting is calm and designed for unwinding, making it easy to relax while technology does its work.
Live Music Performances
Aspen Vacation Rentals homes also place you close to cultural highlights like the Aspen Music Festival and School, one of the premier classical music festivals in the U.S. The summer program spans everything from full orchestra concerts that swell with sound to solo recitals where each note carries through the hall. And if you’re in the mood for something grand, the festival also stages opera performances alive with drama and soaring voices.
Be sure to reserve tickets for Jazz Aspen Snowmass, where the music runs from smooth and soulful to high-energy sets that keep you moving. For an elevated experience, VIP access brings open bars, gourmet meals and raised platforms that offer clearer views of the stage.
Services Designed for Comfort and Convenience
There’s no shortage of luxury with the concierge services that come with an Aspen Vacation Rentals home. They’ll stock the essentials before you arrive, arrange smooth airport transfers and even set up mid-stay housekeeping if you want a refresh. You can book a private chef to cook dinner right in your kitchen, and let the team sort out lift tickets and gear rentals so it’s all ready when you arrive. When it comes to places to stay in Aspen, it’s the extras like this that make everything feel easy.
