Holiday rentals near Aspen Highlands
We found 3,382 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:19 Sept - 26 Sept
Image gallery for Expansive Aspen Core Condo.Unobstructed views of Aspen Mountain and Red Mountain
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Expansive Aspen Core Condo.Unobstructed views of Aspen Mountain and Red Mountain
Aspen, CO
8% off
Price is NZ$9,008
NZ$9,008
NZ$1,287 per night
includes taxes & fees
Image gallery for Mountain Retreat EVSE, Fireplace, Hot Tub, Sonos Theater, 75" & 55" TV, Free Bus
1010 out of 10 rating
Exceptional
(30 reviews)
Mountain Retreat EVSE, Fireplace, Hot Tub, Sonos Theater, 75" & 55" TV, Free Bus
Crested Butte, CO
7% off
Price is NZ$9,966
NZ$9,966
NZ$1,424 per night
includes taxes & fees
Image gallery for Willoughby Way Home with Stunning Aspen Mountain Views
1010 out of 10 rating
Exceptional
(7 reviews)
Willoughby Way Home with Stunning Aspen Mountain Views
Aspen, CO
9% off
Price is NZ$105,966
NZ$105,966
NZ$15,138 per night
includes taxes & fees
Image gallery for On resort in Prospect Development-Summer Oasis w/ Trampoline. Winter Ski In/Out
1010 out of 10 rating
Exceptional
(33 reviews)
On resort in Prospect Development-Summer Oasis w/ Trampoline. Winter Ski In/Out
Crested Butte, CO
8% off
Price is NZ$36,541
NZ$36,541
NZ$5,220 per night
includes taxes & fees
Image gallery for Penthouse #4 Panoramic Views, Hot Tub, 75" & 55" TVs, Sonos, Free Town & Ski Bus
1010 out of 10 rating
Exceptional
(23 reviews)
Penthouse #4 Panoramic Views, Hot Tub, 75" & 55" TVs, Sonos, Free Town & Ski Bus
Crested Butte, CO
7% off
Price is NZ$6,763
NZ$6,763
NZ$966 per night
includes taxes & fees
Image gallery for 4 BR Mountain Side Condo with Heated Pool and Hot Tub! Sleeps 9
1010 out of 10 rating
Exceptional
(108 reviews)
4 BR Mountain Side Condo with Heated Pool and Hot Tub! Sleeps 9
Crested Butte, CO
7% off
Price is NZ$6,198
NZ$6,198
NZ$885 per night
includes taxes & fees
Image gallery for Fox Trot Cabin- On Mountain, Fabulous Views, Hot Tub, Walk to Ski Lifts
1010 out of 10 rating
Exceptional
(17 reviews)
Fox Trot Cabin- On Mountain, Fabulous Views, Hot Tub, Walk to Ski Lifts
Crested Butte, CO
7% off
Price is NZ$23,144
NZ$23,144
NZ$3,306 per night
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
7% off
Price is NZ$23,642
NZ$23,642
NZ$3,377 per night
includes taxes & fees
Image gallery for Great Location at base of Mt! Sleeps 4.
1010 out of 10 rating
Exceptional
(15 reviews)
Great Location at base of Mt! Sleeps 4.
Crested Butte, CO
7% off
Price is NZ$5,859
NZ$5,859
NZ$837 per night
includes taxes & fees
Image gallery for 205 Base area slope side views Mt. Crested Butte. Pet friendly
9.69.6 out of 10 rating
Exceptional
(32 reviews)
205 Base area slope side views Mt. Crested Butte. Pet friendly
Crested Butte, CO
6% off
Price is NZ$3,019
NZ$3,019
NZ$431 per night
includes taxes & fees
Image gallery for Ski in- ski out 3bd 2ba Modern Contemporary At Capitol Peak Base Village
1010 out of 10 rating
Exceptional
(20 reviews)
Ski in- ski out 3bd 2ba Modern Contemporary At Capitol Peak Base Village
Snowmass Village, CO
12% off
Price is NZ$22,484
NZ$22,484
NZ$3,212 per night
includes taxes & fees
Image gallery for Ski-In/Out Slopeside Mountain 3BR Retreat. Gorgeous Views and Sunsets!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Ski-In/Out Slopeside Mountain 3BR Retreat. Gorgeous Views and Sunsets!
Crested Butte, CO
7% off
Price is NZ$5,335
NZ$5,335
NZ$762 per night
includes taxes & fees
Image gallery for Epic Top Floor Luxury Summer Retreat in Snowmass Base Village!
1010 out of 10 rating
Exceptional
(5 reviews)
Epic Top Floor Luxury Summer Retreat in Snowmass Base Village!
Snowmass Village, CO
8% off
Price is NZ$11,753
NZ$11,753
NZ$1,679 per night
includes taxes & fees
Image gallery for Designer Condo #2: Epic Views, Hot Tub, 75" & 55" TVs, Sonos, Free Town/Ski Bus
1010 out of 10 rating
Exceptional
(19 reviews)
Designer Condo #2: Epic Views, Hot Tub, 75" & 55" TVs, Sonos, Free Town/Ski Bus
Crested Butte, CO
7% off
Price is NZ$6,763
NZ$6,763
NZ$966 per night
includes taxes & fees
Image gallery for Food & Wine Discount In Core, Never Drive! Pool. Hot Tub. Private Corner Unit.
9.89.8 out of 10 rating
Exceptional
(50 reviews)
Food & Wine Discount In Core, Never Drive! Pool. Hot Tub. Private Corner Unit.
Aspen, CO
8% off
Price is NZ$10,001
NZ$10,001
NZ$1,429 per night
includes taxes & fees
Image gallery for Charming Aspen Central Victorian; 4 Bedrooms, Walk to Gondola
1010 out of 10 rating
Exceptional
(21 reviews)
Charming Aspen Central Victorian; 4 Bedrooms, Walk to Gondola
Aspen, CO
8% off
Price is NZ$28,187
NZ$28,187
NZ$4,027 per night
includes taxes & fees
Image gallery for Aspen Mountain, Ski in/out, Panoramic Mountain Views, 1.5 Blocks To Gondola
9.89.8 out of 10 rating
Exceptional
(96 reviews)
Aspen Mountain, Ski in/out, Panoramic Mountain Views, 1.5 Blocks To Gondola
Aspen, CO
7% off
Price is NZ$17,294
NZ$17,294
NZ$2,471 per night
includes taxes & fees
Image gallery for Getaway in CB @ this 3 bedroom Treasury Point Condo, Best Views! Common Hot Tub
9.69.6 out of 10 rating
Exceptional
(34 reviews)
Getaway in CB @ this 3 bedroom Treasury Point Condo, Best Views! Common Hot Tub
Crested Butte, CO
7% off
Price is NZ$4,944
NZ$4,944
NZ$706 per night
includes taxes & fees
Image gallery for SPACIOUS TOWNHOME WITH BEAUTIFUL MOUNTAIN VIEWS
1010 out of 10 rating
Exceptional
(19 reviews)
SPACIOUS TOWNHOME WITH BEAUTIFUL MOUNTAIN VIEWS
Crested Butte, CO
7% off
Price is NZ$6,862
NZ$6,862
NZ$980 per night
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
8% off
Price is NZ$51,906
NZ$51,906
NZ$7,415 per night
includes taxes & fees
Image gallery for Penthouse #1: Panoramic Views, Hot Tub, 75" & 55" TVs, Sonos, Free Ski Bus
1010 out of 10 rating
Exceptional
(54 reviews)
Penthouse #1: Panoramic Views, Hot Tub, 75" & 55" TVs, Sonos, Free Ski Bus
Crested Butte, CO
7% off
Price is NZ$6,763
NZ$6,763
NZ$966 per night
includes taxes & fees
Image gallery for Designer Condo #3: Views, Hot Tub, Fireplace, 75" & 55" TVs, Sonos, Town/Ski Bus
1010 out of 10 rating
Exceptional
(7 reviews)
Designer Condo #3: Views, Hot Tub, Fireplace, 75" & 55" TVs, Sonos, Town/Ski Bus
Crested Butte, CO
7% off
Price is NZ$6,754
NZ$6,754
NZ$965 per night
includes taxes & fees
Image gallery for Tastefully Remodeled, Spacious,Luxury, Calm and Peaceful
1010 out of 10 rating
Exceptional
(73 reviews)
Tastefully Remodeled, Spacious,Luxury, Calm and Peaceful
Crested Butte, CO
9% off
Price is NZ$3,559
NZ$3,559
NZ$508 per night
includes taxes & fees
Image gallery for 223 Slope side base area Mt CB. Pet friendly
9.49.4 out of 10 rating
Exceptional
(31 reviews)
223 Slope side base area Mt CB. Pet friendly
Crested Butte, CO
6% off
Price is NZ$2,773
NZ$2,773
NZ$396 per night
includes taxes & fees
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Find the best place to stay - Aspen Highlands
Showing deals for: 13 Sept - 16 Sept
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)
The current price is NZ$24,540
NZ$24,540
for 3 nights, 1 home
NZ$8,180 per night
includes taxes & fees
Aspen Haven By Luxuri
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is NZ$8,849
NZ$8,849
for 3 nights, 1 apartment
NZ$2,950 per night
includes taxes & fees
Stunning View Red Mtn Property 2 Min From Town
Sleeps 12 · 7 bedrooms · 6+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
The current price is NZ$25,568
NZ$25,568
for 3 nights, 1 home
NZ$8,523 per night
includes taxes & fees
Aspen Mountain Lodge
Sleeps 4 · 1 bedroom
8.28.2 out of 10
Very goodvery good
994 reviews(994 reviews)
The current price is NZ$1,709
NZ$1,709
for 3 nights, 1 room
NZ$570 per night
includes taxes & fees
Colorful Cabin w/ Teepee, Fire Pits & Mtn Views!
Sleeps 4 · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
102 reviews(102 reviews)
The current price is NZ$1,352
NZ$1,352
for 3 nights, 1 cabin
NZ$451 per night
includes taxes & fees
Aspen Paradise! Relax & entertain indoors and outdoors in comfort and serenity.
Sleeps 10 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
The current price is NZ$11,708
NZ$11,708
for 3 nights, 1 home
NZ$3,903 per night
includes taxes & fees
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
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