What are the top rated Winter Rentals in Aspen?

There are a lot of options in Aspen. If you plan on staying in the Aspen area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Aspen: <a href="/property/penthouse-chateau-roaring-fork-ac-all-day-sun-views-available-food-wine/HA-121326856" class="class="static-page-link"">PENTHOUSE &#34;CHATEAU ROARING FORK&#34;, AC, ALL DAY SUN, VIEWS-AVAILABLE FOOD-WINE</a> <a href="/property/a-c-the-only-3-king-bedroom-3-en-suite-baths-on-aspen-mtn-steps-to-lil-nell/HA-321515374" class="class="static-page-link"">A/C &amp; The Only 3 King Bedroom; 3 En Suite Baths On Aspen Mtn, Steps To Lil Nell</a> <a href="/property/gondola-plaza-adjacent-with-treehouse-views-over-aspen/HA-121950424" class="class="static-page-link"">Gondola Plaza adjacent with treehouse views over Aspen</a> <a href="/property/luxury-estate-w-pool-spa-6-miles-to-town-featured-in-dwell-magazine/HA-321630653" class="class="static-page-link"">Luxury Estate w- Pool/Spa, 6 Miles To Town, Featured In Dwell Magazine</a> <a href="/property/deluxe-private-townhome-minutes-walk-to-aspen-mountain-skiing-and-downtown/HA-3211762398" class="class="static-page-link"">Deluxe private townhome minutes walk to Aspen Mountain skiing and downtown!</a> <a href="/property/aspen-riverhouse-riverfront-family-vacation/HA-3215225" class="class="static-page-link"">Aspen Riverhouse-Riverfront Family Vacation</a> <a href="/property/charming-3-bedroom-family-house-with-hot-tub-on-2-acres-panoramic-views/HA-3211024304" class="class="static-page-link"">Charming 3 Bedroom family house with hot tub on 2 acres panoramic views</a> <a href="/property/3-bed-3-bath-in-town-aspen-luxury-king-2-queen-bed-w-d-ac-parking-balcony-wifi/HA-3212092080" class="class="static-page-link"">3 Bed/3 Bath In Town Aspen Luxury King &amp; 2 Queen Bed W/D AC Parking Balcony Wifi</a> <a href="/property/pet-friendly-luxurious-3-bedroom-aspen-condo/HA-3211512802" class="class="static-page-link"">Pet Friendly &amp; Luxurious 3 bedroom Aspen Condo</a> <a href="/property/ski-in-ski-out-at-aspen-mountain-shadow-mtn-lift-access-hot-tub-fireplace-mountain-facing-views/HA-1217657652" class="class="static-page-link"">Ski-In/Ski-Out at Aspen Mountain! Shadow Mtn Lift Access, Hot Tub, Fireplace &amp; Mountain-Facing Views</a>

How much does it cost to rent a place to stay near Aspen in the wintertime?

The average cost for winter rentals in Aspen is $2,508 per night. Ownerdirect has a wide list of great winter places to stay near Aspen that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Aspen that allow pets?

Yes, here are the top cottage/chalet rentals in Aspen that allow you to bring your pet or dog: Central AC, Updated 4 BR, 4-5 BA Townhouse, Pool Winter Views on Aspen’s Main St! Walk to Everything! Balcony, Gas FP, Elevator, Parking, Hot tub Château Chaumont by Snowmass Vacations Renovated Riverfront 3 BR, 2 BA with Pool - Walk to Town! See all <a href="/all/usa/colorado/aspen/pet-friendly-rentals" class="class=&#34;static-page-link&#34;">pet-friendly vacation rentals in Aspen</a> on Ownerdirect

Do you have any winter rentals in Aspen that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Aspen to find what works for you.

Are there winter accommodations in Aspen that have indoor swimming pools?

As of 2026, the data from Ownerdirect shows that there are over 2634 private swimming pools or indoor pools accommodations near Aspen along with other great amenities.