Aspen Winter Rentals & Holiday Homes
Discover winter rentals Aspen - We found 307 exact matches
When do you want to travel?
- Air Conditioner
- Parking
- Pool
- Wheelchair Accessible
- Balcony/Terrace
- Accessibility
- Parking
- Pool
- TV
- Air Conditioner
- Pool
- Accessibility
- Air Conditioner
- Parking
- Pet Friendly
- Wheelchair Accessible
- Balcony/Terrace
- Accessibility
- Air Conditioner
- Parking
- TV
- Parking
- Pool
- TV
- Air Conditioner
- Parking
- Pool
- Parking
- Pool
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Parking
- Pool
- TV
- Parking
- Pool
- TV
- Parking
- Pool
- TV
- Parking
- Pool
- TV
- Parking
- Pool
- TV
- Parking
- Pet Friendly
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
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:
- PENTHOUSE "CHATEAU ROARING FORK", AC, ALL DAY SUN, VIEWS-AVAILABLE FOOD-WINE
- The Aspen Mountain Residences [Formerly Hyatt Grand Aspen] at Owner Direct Rates
- Best House In Aspen For ALL SEASONS! Mega Mansion in ideal location!
- 2BD Ritz-Carlton Club Aspen - Ski-in & Ski-out - Most Dates Available
- Avail: Xmas, March 7-14, Mar 14-21, Mar 21-28, Mar 28-Apr 4 & Apr 4-11 weeks!
- Aspen Highlands House ski-in ski-out; Ritz Carlton privileges; free taxi to town
- Awesome views of the slopes & pool. Enjoy all of the Ritz Carlton amenities!
- Ritz Carlton Club Aspen Highlands. 3 Bdrm 3 bath. 2026 Dates Available
- Spring Break 3/29-Ritz Carlton Aspen, 3 BR, Balcony w/Slopes View, Ski in-out!
- Amazing 2br 3ba Condo is Perfect for Aspen!
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 $2,401 per night. Unpluggedweekend 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:
- Aspen Mountain Views, Bright Top-Floor 3BR, Pool, Hot Tub, 7-Min Walk to Gondola
- Aspen Meadows Resort 111
- Aspen Alps
- Aspen Mountain Views, Bright Corner 2BR, Pool, Hot Tub, 7-Min Walk to Gondola
See all pet-friendly vacation rentals in Aspen on Unpluggedweekend
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 Unpluggedweekend shows that there are over 307 private swimming pools or indoor pools accommodations near Aspen along with other great amenities.
