Book Holiday Homes in Aspen

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Aspen Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Aspen vacation homes are the perfect way for you to wing it.

Holiday houses in Aspen let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Aspen in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Aspen adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Aspen with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Aspen vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Top trending hotels in Aspen

The Inn at Aspen

The Inn at Aspen

3.5 out of 5
38750 CO-82, Aspen, CO
Stay at this 3.5-star ski hotel in Aspen. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in ...
The Inn at Aspen
The Gant

The Gant

4 out of 5
610 SOUTH WEST END STREET, Aspen, CO
The price is NZ$1,771 per night from 9 Jan to 10 Jan
NZ$1,771
includes taxes & fees
9 Jan - 10 Jan 2025
Stay at this 4-star boutique condo in Aspen. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
The Gant
St. Moritz Lodge & Condominiums

St. Moritz Lodge & Condominiums

2.5 out of 5
334 W Hyman Ave, Aspen, CO
The price is NZ$444 per night from 6 Jan to 7 Jan
NZ$444
includes taxes & fees
6 Jan - 7 Jan 2025
Book a stay at this ski hotel in Aspen. Enjoy free WiFi, free parking, and a free ski shuttle. Our guests praise the breakfast and the pool in our reviews. Popular ...
St. Moritz Lodge & Condominiums
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The St. Regis Aspen Resort

The St. Regis Aspen Resort

5 out of 5
315 East Dean St., Aspen, CO
The price is NZ$3,941 per night from 19 Jan to 20 Jan
NZ$3,941
includes taxes & fees
19 Jan - 20 Jan 2025
Stay at this 5-star luxury resort in Aspen. Enjoy free WiFi, a full-service spa, and 3 restaurants. Popular attractions Aspen Mountain and Buttermilk Mountain ...
The St. Regis Aspen Resort
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.