Your Ultimate Ski to Summer Aspen Guide

For a quintessential Colorado adventure, an Aspen luxury vacation rental seamlessly blends R+R with the thrill of mountain living.

Aspen provides a storybook setting to play out all of your Western ski dreams. This alpine town is filled with an exciting range of activities in culmination with its four diverse mountains. Whether it’s racing through Aspen Mountain – known as Ajax – or taking a guided hike through the Highland Bowl, the region’s stunning landscapes offer endless possibilities as you chart your own outdoor adventure. To help you figure out how to make the most of Aspen, our friends at Cuvée provide their vetted recommendations of what to do, where to stay, and more.

How to get to Aspen

Aspen, Colorado’s renowned mountains are accessible via four airports: Aspen/Pitkin County, Eagle County, Grand Junction Regional, and Denver International Airport. Depending on where you’re coming from or flying commercial or private, our Smarties can pair you with the best routing. Alternatively, if you live out West, eliminate the airport altogether with a road trip through region’s rich wilderness. Regardless of where you arrive from, your SmartFlyer advisor can secure you a car rental or private transfer through the breathtaking scenery to your Aspen luxury vacation rental should you wish to have a driver.

Where to Stay in Aspen for Skiing

Much like its diverse ski scene, Aspen offers a wide range of accommodations tailored to your various needs. For those seeking more than a hotel suite, SmartFlyer offers vetted luxury rentals through our partners at Cuvée. This boutique firm is differentiated from your mass market rental companies in a big way. They exclusively own as well as manage their curated collection of homes. The Cuvée team also painstakingly assessed architecture, design, technology, and even views for over a decade as they’ve built up their reputable portfolio.

Aspen remains one of Cuvée’s premier destinations with over eleven exclusive estates available to discerning guests. Each home is tailored to provide a distinct experience. Whether you’re seeking a ski-in ski-out chalet or want to be located near a landmark within the community’s downtown, Cuvée’s Aspen luxury vacation rentals are well-equipped. And by booking through your SmartFlyer advisor, you’ll be sure to have pre-arranged amenities ranging from a chef-prepared welcome reception to premium wines and spirits awaiting your arrival.

If you need a TL;DR, we’ve rounded up our Smartie picks for an Aspen luxury vacation rental with Cuvée.

Earn Your Après

Aspen has earned a reputation for being one of the most stylish stateside skiing spots, replete with ways to work your way back to your rental for an après experience. But first, the reason you’re here…to ski!  For those who have trepidation around the slopes, consider Nordic-style cross-country skiing. The White River National Forest is filled with serene meadows as well as frozen creeks laden with snow to consider for cross-country skiing.

On the complete opposite end of the spectrum, heli-skiing presents a thrill for those who love an adrenaline rush. With the help of your SmartFlyer travel advisor, you’ll be privately chartered to Telluride to enjoy this bucket list downhill adventure with trained experts. But whether you opt for high flying or prefer to stick to cross-country, the Cuvée team will make sure an après soirée is ready for your return from the comfort of your private, in-residence.

Alternative Aspen Adventures

If you’re looking to find a unique winter activity, then Aspen has plenty of excursions to complement your time on the slopes. Summiting the peaks of Vail Valley on a snowshoe tour is an invigorating option to get your workout in without relying on the resort lifts. Alternatively, guided backcountry snowmobiling also provides you a straight shot to the summit for a private chef-prepared lunch in a cozy mountain hut. For the avid shopper, take a piece of Colorado home by working with Kemo Sabe’s expert crafters to create your one-of-a-kind mountain-chic hat. Or, for postcard-worthy views of the Rockies, your SmartFlyer travel advisor can also work to arrange a hot air balloon ride.

Smartie Picks for Aspen Dining

Cuvée’s private culinary team is well-equipped to serve any cuisine you desire at your Aspen luxury vacation rental. The team works closely with local Chef “Jimbo” Jimena whose cuisine embraces Aspen’s rich reverence for nature and community. From shopping, cooking, and wine pairing to clean-up and evening entertainment, her team ensures a memorable in-house experience. But if you’re itching to explore town, check out our top dining reccos across Aspen.

Cache Cache: To truly indulge in Cache Cache’s classic French cuisine, pick up their 100-page wine list and go for a full-course pursuit. We recommend beginning with a fois gras on a toasted baguette, followed by a mouth-watering rack of lamb with potatoes au gratin. Finally, top it all off with a decadent house biscotti with espresso ice cream.

Matsuhisa: Chef Nobu Matsuhisa’s name is synonymous with elevated Japanese cuisine, and this restaurant is no exception. Dining at the sushi bar here is a must: taste your way through fresh sushi with a twist of South American flare, as well as their premium imported sakes. Reservations required.

Pine Creek Cookhouse: Pine Creek Cookhouse is Aspen’s remote and cherished dining experience within the Elk Mountains. Work with your SmartFlyer travel advisor and the Cuvée team for a guided ride to the restaurant by the popular American Lake and Cathedral Lake trails in summer or a horse-drawn sleigh in winter. Afterwards, enjoy Chef Chris Keating’s organic three delectable courses and house favorites like their stuffed Nepalese dumplings and s’mores fondue.

Ajax Tavern: This iconic spot is a local favorite where you can hop off the slopes and head directly to its mountainside patio for some truffle fries and champagne. The French-American Tavern cuisine also runs from lunch straight into the night, preparing dishes with fresh ingredients served with craft cocktails.

The White House Tavern: Tucked in a historic white cottage on the corner of well-traveled Aspen streets, we love this restaurant’s hearty salads and sandwiches. The atmosphere is also quintessentially Colorado, fit with warm, wood-paneled aesthetics and a lively atmosphere all day long.

French Alpine Bistro: If you’re looking for romance in the Rockies, then reserve a table at this charming chalet-inspired restaurant. This is the spot to visit for ultra-private French Cuisine in the Colorado Rockies. Cozy up in the candle-lit dining room or snag a spot at a coveted bar seat to get a front-row view of the open kitchen.

Itching for an Aspen luxury vacation rental? Contact your SmartFlyer travel advisor to begin planning your Rocky Mountain getaway.



White River National Forest
Vail Valley
Aspen Hatter, 465 N Mill St #14, Aspen, CO 81611

Villa Rental Stays

1001 Estate
The Mother Lode
Mountian Forge
Red Mountain Rise
Aspen Sleek


Cache Cache 205 S Mill St, Aspen, CO 81611
Matsuhisa 303 E Main St, Aspen, CO 81611
Pine Creek Cookhouse 11399 Castle Creek Rd, Aspen, CO 81611
Ajax Tavern 685 E Durant Ave, Aspen, CO 81611
The White House Tavern 302 E Hopkins Ave, Aspen, CO 81611
French Alpine Bistro 400 E Hopkins Ave, Aspen, CO 81611


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