Aspen Winter Rentals & Holiday Homes
Discover winter rentals Aspen - We found 2640 exact matches
When do you want to travel?
- Parking
- TV
- Balcony/Terrace
- Pool
- Wheelchair Accessible
- Breakfast
- Parking
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- TV
- Parking
- Breakfast
- Child Friendly
- Air Conditioner
- Parking
- Pool
- Parking
- Wheelchair Accessible
- Child Friendly
- Parking
- Pool
- TV
- Parking
- Internet
- Parking
- TV
- Accessibility
- Air Conditioner
- Parking
- TV
- Parking
- Pet Friendly
- TV
- Air Conditioner
- Parking
- TV
- Parking
- TV
- Balcony/Terrace
- Parking
- Pool
- TV
- Parking
- TV
- Balcony/Terrace
- Parking
- TV
- Balcony/Terrace
- Parking
- TV
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Parking
- TV
- Security/Safety
- Parking
- TV
- Balcony/Terrace
- Air Conditioner
- Parking
- Pool
- Parking
- TV
- Balcony/Terrace
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:
- Winter Views on Aspen’s Main St! Walk to Everything! Balcony, Gas FP, Elevator, Parking, Hot tub
- Downtown Aspen Studio - walk to everything!
- PENTHOUSE "CHATEAU ROARING FORK", AC, ALL DAY SUN, VIEWS-AVAILABLE FOOD-WINE
- A/C & The Only 3 King Bedroom; 3 En Suite Baths On Aspen Mtn, Steps To Lil Nell
- Gondola Plaza adjacent with treehouse views over Aspen
- The Aspen Mountain Residences [Formerly Hyatt Grand Aspen] at Owner Direct Rates
- Luxury Estate w- Pool/Spa, 6 Miles To Town, Featured In Dwell Magazine
- Deluxe private townhome minutes walk to Aspen Mountain skiing and downtown!
- Aspen Riverhouse-Riverfront Family Vacation
- Charming 3 Bedroom family house with hot tub on 2 acres panoramic views
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 $2,485 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:
- Heart of Aspen 2BR/2BA — Walk to Gondola, Quiet & Convenient
- Chateau Eau Claire #9
- Château Chaumont by Snowmass Vacations
- The Woody Creek Chalet on the Roaring Fork River
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 2640 private swimming pools or indoor pools accommodations near Aspen along with other great amenities.
