Holiday rentals near Aspen Highlands
We found 3,362 holiday rentals — enter your dates for availability
If you'd like to stay close to Aspen Highlands, scroll through and discover private holiday rentals to choose your home away from home. Whether you're staying in a holiday rental with family or friends, you'll have the amenities that you expect and more, which might include air conditioning and a pool. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Aspen Highlands
Showing deals for:21 Nov - 28 Nov
Image gallery for Location! Fresh, Modern, Central Hideaway
1010 out of 10 rating
Exceptional
(9 reviews)
Location! Fresh, Modern, Central Hideaway
Aspen, CO
10% off
Price is AU$10,454
AU$10,454
AU$1,493 nightly
Includes taxes & fees
Image gallery for Aspen Paradise! Relax & entertain indoors and outdoors in comfort and serenity.
1010 out of 10 rating
Exceptional
(32 reviews)
Aspen Paradise! Relax & entertain indoors and outdoors in comfort and serenity.
Aspen, CO
8% off
Price is AU$25,570
AU$25,570
AU$3,653 nightly
Includes taxes & fees
Image gallery for On resort in Prospect Development-Direct Ski In/Out-Trampoline-Views
1010 out of 10 rating
Exceptional
(36 reviews)
On resort in Prospect Development-Direct Ski In/Out-Trampoline-Views
Crested Butte, CO
8% off
Price is AU$21,811
AU$21,811
AU$3,116 nightly
Includes taxes & fees
Image gallery for Aspen Riverhouse-Riverfront Family Vacation
1010 out of 10 rating
Exceptional
(70 reviews)
Aspen Riverhouse-Riverfront Family Vacation
Aspen, CO
9% off
Price is AU$12,998
AU$12,998
AU$1,857 nightly
Includes taxes & fees
Image gallery for Great location, Gorgeous View- Renovated- New Rental
1010 out of 10 rating
Exceptional
(9 reviews)
Great location, Gorgeous View- Renovated- New Rental
Snowmass Village, CO
8% off
Price is AU$5,408
AU$5,408
AU$773 nightly
Includes taxes & fees
Image gallery for BEST RATES IN ASPEN, BASALT VALLEY, INQUIRE FOR LAST MINUTE DISCOUNTS
9.89.8 out of 10 rating
Exceptional
(28 reviews)
BEST RATES IN ASPEN, BASALT VALLEY, INQUIRE FOR LAST MINUTE DISCOUNTS
Basalt, CO
8% off
Price is AU$5,923
AU$5,923
AU$846 nightly
Includes taxes & fees
Image gallery for Best House In Aspen For ALL SEASONS! Mega Mansion in ideal location!
1010 out of 10 rating
Exceptional
(20 reviews)
Best House In Aspen For ALL SEASONS! Mega Mansion in ideal location!
Aspen, CO
9% off
Price is AU$44,193
AU$44,193
AU$6,313 nightly
Includes taxes & fees
Image gallery for YULE CREEK LODGE-Quintessential Mountain Cabin on 53 Private Acres
1010 out of 10 rating
Exceptional
(123 reviews)
YULE CREEK LODGE-Quintessential Mountain Cabin on 53 Private Acres
Carbondale, CO
8% off
Price is AU$3,415
AU$3,415
AU$488 nightly
Includes taxes & fees
Image gallery for Luxurious Riverfront Cabin on the Frying Pan River - 1 block to Basalt
1010 out of 10 rating
Exceptional
(93 reviews)
Luxurious Riverfront Cabin on the Frying Pan River - 1 block to Basalt
Basalt, CO
8% off
Price is AU$6,916
AU$6,916
AU$988 nightly
Includes taxes & fees
Image gallery for Suite 153 at Perfect Location w Pool & Hot Tub
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Suite 153 at Perfect Location w Pool & Hot Tub
Crested Butte, CO
10% off
Price is AU$2,442
AU$2,442
AU$349 nightly
Includes taxes & fees
Image gallery for Open, Airy Mountaintop Home
1010 out of 10 rating
Exceptional
(37 reviews)
Open, Airy Mountaintop Home
Carbondale, CO
8% off
Price is AU$2,942
AU$2,942
AU$420 nightly
Includes taxes & fees
Image gallery for Great Location at base of Mt! Sleeps 4.
1010 out of 10 rating
Exceptional
(16 reviews)
Great Location at base of Mt! Sleeps 4.
Crested Butte, CO
7% off
Price is AU$5,345
AU$5,345
AU$764 nightly
Includes taxes & fees
Image gallery for Expansive Aspen Core Condo.Unobstructed views of Aspen Mountain and Red Mountain
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Expansive Aspen Core Condo.Unobstructed views of Aspen Mountain and Red Mountain
Aspen, CO
8% off
Price is AU$8,392
AU$8,392
AU$1,199 nightly
Includes taxes & fees
Image gallery for Get to know the NEW CIRQUE VICEROY in Snowmass Village!! #464
1010 out of 10 rating
Exceptional
(5 reviews)
Get to know the NEW CIRQUE VICEROY in Snowmass Village!! #464
Snowmass Village, CO
8% off
Price is AU$10,082
AU$10,082
AU$1,440 nightly
Includes taxes & fees
Image gallery for 279-281 Base area 2 room 2 bath unit sleeps 6 Mt. Crested Butte
9.29.2 out of 10 rating
Wonderful
(26 reviews)
279-281 Base area 2 room 2 bath unit sleeps 6 Mt. Crested Butte
Crested Butte, CO
8% off
Price is AU$6,521
AU$6,521
AU$932 nightly
Includes taxes & fees
Image gallery for Studio at Grand Lodge, Hot Tub, Pool, Pet Friendly
8.48.4 out of 10 rating
Very good
(7 reviews)
Studio at Grand Lodge, Hot Tub, Pool, Pet Friendly
Crested Butte, CO
10% off
Price is AU$2,577
AU$2,577
AU$368 nightly
Includes taxes & fees
Image gallery for Charming, Classy, Ski-in Condo in Superior Location!
1010 out of 10 rating
Exceptional
(108 reviews)
Charming, Classy, Ski-in Condo in Superior Location!
Snowmass Village, CO
8% off
Price is AU$3,854
AU$3,854
AU$551 nightly
Includes taxes & fees
Image gallery for Ski-Accessible-during main season-Condo In Snowmass Village, CO - with Hot Tub!
9.69.6 out of 10 rating
Exceptional
(72 reviews)
Ski-Accessible-during main season-Condo In Snowmass Village, CO - with Hot Tub!
Snowmass Village, CO
8% off
Price is AU$6,101
AU$6,101
AU$872 nightly
Includes taxes & fees
Image gallery for Exquisite pet friendly home, 5 blks from Gondola with stunning views!!
1010 out of 10 rating
Exceptional
(42 reviews)
Exquisite pet friendly home, 5 blks from Gondola with stunning views!!
Aspen, CO
8% off
Price is AU$9,087
AU$9,087
AU$1,298 nightly
Includes taxes & fees
Image gallery for Updated, Modern Mountain Condo w/ Fireplace, Pool, Hot Tub, Walk to Base Village
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Updated, Modern Mountain Condo w/ Fireplace, Pool, Hot Tub, Walk to Base Village
Snowmass Village, CO
7% off
Price is AU$4,402
AU$4,402
AU$629 nightly
Includes taxes & fees
Image gallery for New Luxury Two Level 4 Bedroom - 4.5 Bath Condo!
1010 out of 10 rating
Exceptional
(11 reviews)
New Luxury Two Level 4 Bedroom - 4.5 Bath Condo!
Aspen, CO
8% off
Price is AU$27,450
AU$27,450
AU$3,921 nightly
Includes taxes & fees
Image gallery for SKI-IN-SKI-OUT Chalet. 1 of 2 Houses at the Base of Mt Crested Butte.
1010 out of 10 rating
Exceptional
(21 reviews)
SKI-IN-SKI-OUT Chalet. 1 of 2 Houses at the Base of Mt Crested Butte.
Crested Butte, CO
8% off
Price is AU$20,215
AU$20,215
AU$2,888 nightly
Includes taxes & fees
Image gallery for Top Floor Timbers Condo in Mt. Crested Butte
9.89.8 out of 10 rating
Exceptional
(181 reviews)
Top Floor Timbers Condo in Mt. Crested Butte
Crested Butte, CO
7% off
Price is AU$2,088
AU$2,088
AU$298 nightly
Includes taxes & fees
Image gallery for Modern, MTN Retreat w/ Fireplace, Pool, Hot Tub, Steps to Snowmass Base Village
1010 out of 10 rating
Exceptional
(12 reviews)
Modern, MTN Retreat w/ Fireplace, Pool, Hot Tub, Steps to Snowmass Base Village
Snowmass Village, CO
8% off
Price is AU$4,190
AU$4,190
AU$599 nightly
Includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Aspen Highlands
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Find the best place to stay - Aspen Highlands
Ritz Carlton Club - Ski in/Out-*Best Prices* (All Dates Avail)
Sleeps 8 · 3 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Ritz Carlton Club - Ski in/Out-*Best Prices* (All Dates Avail)
Sleeps 6 · 2 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
Best House In Aspen For ALL SEASONS! Mega Mansion in ideal location!
Sleeps 11 · 5 bedrooms · 6 bathrooms
1010 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
Spacious Multi-Level Townhome in Mountain View with Gas Fireplace, Grill, Parking, & Large Patio!
Sleeps 8 · 4 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Ritz Carlton Club best price ski ski Aspen Highlands
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Victorian House in the Core of Aspen. Short Walk To Gondola
Sleeps 28 · 13 bedrooms · 13+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value