Aspen Winter Rentals & Holiday Homes
Discover winter rentals Aspen - We found 2594 exact matches
About Aspen Winter Rental on Top Winter Vacations
Planning on a winter vacation in Aspen? Discover 2594 places to stay in Aspen, for those traveling with their family, friends, in groups, or for a wedding retreat.
At Top Winter Vacations, we have a wide range of listings for accommodations in Aspen, CO that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. Top Winter Vacations winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Aspen winter accommodation starts at US $2,465, and the most popular properties in Aspen are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, Top Winter Vacations will make your winter trip memorable.
Top Winter Vacations offers a great deal for travelers planning on renting a place in Aspen, to enjoy these benefits and to book your winter vacation homes, go to Top Winter Vacations filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Aspen and unlock even more amazing deals.
Frequently Asked Questions About Aspen Winter Rental
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:
- Deluxe private townhome minutes walk to Aspen Mountain skiing and downtown!
- Gondola Plaza adjacent with treehouse views over Aspen
- 3 Bed/3 Bath In Town Aspen Luxury King & 2 Queen Bed W/D AC Parking Balcony Wifi
- Aspen Condo 1.5 Blocks to Town. Balcony. Outdoor Pool. Sleeping Den w/Sofa Bed, 3 Bathrooms, Gas FP
- Beautiful modern Aspen Core Condo- 2 Bed 2 Bath, AC, pool and hot tub
- Riverfront Designer 2 BR, Walk to Gondola!
- Exquisite pet friendly home, 5 blks from Gondola with stunning views!
- 9 Million Luxury Residence at “Monarch On the Park”Downtown Aspen with Parking
- Owner-Managed 2BR/2BA in Aspen Core – Walk to Gondola, Quiet & Convenient
- Remodeled Aspen Gem! 1 Block to Aspen Mtn, Balcony with Views, W/D, Parking & Walk to Town
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 $2,465 per night. Topwintervacations 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:
- The Woody Creek Chalet on the Roaring Fork River
- Chateau Eau Claire #9
- The Aspen Mountain Residences 23AB - 2 Bedroom
- Aspen Mountain Views, Bright Top-Floor 3BR, Pool, Hot Tub, 7-Min Walk to Gondola
See all pet-friendly vacation rentals in Aspen on Topwintervacations
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 Topwintervacations shows that there are over 2594 private swimming pools or indoor pools accommodations near Aspen along with other great amenities.
