351+ Vacation Rentals Near Aspen Highlands |
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Top Winter Vacations - Vacation Rentals in Aspen Highlands

Property Image From US $466
         

10.0 (28 Reviews)
Cabin
River's Edge | Experience Maroon Bells @ T-Lazy 7
  • TV
  • Security/Safety
  • Wellness Facilities

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Property Image From US $575
         

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10.0 (2 Reviews)
House
Le Chamonix #11 Aspen Highlands
  • Security/Safety
  • Sports/Activities
  • Skiing

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Property Image From US $3,431
         

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New
House
Aspen Ritz Carlton 3 bed Premier 02
  • Parking
  • Pool
  • TV

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Property Image From US $1,877
         

10.0 (12 Reviews)
Condo
Ritz Carlton Club - Great Rates
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $5,648
         

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10.0 (1 Review)
House
The Ritz-Carlton Club, 3 BR Residence 8204, Ski-in/Ski-out Resort in Aspen w/Courtyard View
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $3,155
         

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New
Condo
Aspen Ritz Carlton 3 Bedroom Residence
  • Parking
  • Pool
  • TV

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Property Image From US $1,329
         

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10.0 (6 Reviews)
Condo
RITZ CARLTON CLUB-ALL DAYS-ALL WEEKS LOWEST PRICE-OVER 200 VRBO REVIEWS
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $3,155
         

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9.0 (1 Review)
Apartment
Aspen Ritz-Carlton 3 Bedroom Ski In, Ski Out Residence With Access To Slopeside Heated Pools And Hot Tubs
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $3,155
         

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New
Apartment
Aspen Ritz Carlton 3 Bed Premier
  • Parking
  • Pool
  • TV

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Property Image From US $1,760
         

10.0 (3 Reviews)
Condo
Ritz Carlton Club Aspen Highlands. 2.21 - 2.28.26 only. 3 Bdrm 3 bath. Elkhorn
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $1,957
         

10.0 (2 Reviews)
House
Winter Retreat! Mountain Home w/Hot Tub, Spacious Deck, Balconies & Peaceful Forest Views
  • Air Conditioner
  • Parking
  • TV

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Property Image From US $1,020
         

10.0 (1 Review)
House
Elegant mountain escape with stunning view, spacious deck & fireplace
  • Parking
  • TV
  • Balcony/Terrace

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Property Image From US $816
         

9.6 (11 Reviews)
Condo
Ritz Carlton Residences Ski In Out LUX 2 Bedroom 2.5 Bth Kitchen WD Pool Spa Gym
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $1,241
         

9.4 (23 Reviews)
Condo
Spacious Winter Townhome w/Mountain Views! Gas FP, Patio, Grill & Parking, Multi-Level Comfort
  • Parking
  • TV
  • Balcony/Terrace

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Property Image From US $5,842
         

New
House
Elegant Tiehack Estate
  • Air Conditioner
  • Parking
  • TV

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Property Image From US $5,142
         

New
Condo
The Ritz-Carlton Club | 3BR Premier Residence 8303, Ski-in/Ski-out, Aspen Highlands with Ski View
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $4,928
         

New
Condo
The Ritz-Carlton Club | Two-Bedroom Residence 8415, Ski-in & Ski-out Resort in Aspen Highlands
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $4,928
         

New
Condo
The Ritz-Carlton Club | 3 Bedroom Residence 8105, Ski-in & Ski-out Resort in Aspen Highlands
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $4,928
         

New
Condo
The Ritz-Carlton | 2 BR Residence 8409, Mountain/Mall view, Ski-in/Ski-out in Aspen Highlands
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $4,858
         

New
Condo
The Ritz-Carlton Club | 3 BR Residence 8204, Ski-in/Ski-out Resort in Aspen w/Courtyard View
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $4,714
         

New
Condo
The Ritz-Carlton Club | 3 Bedroom Residence WR 2309, Ski-in & Ski-out Resort in Aspen Highlands
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $4,372
         

New
Condo
World class retreat; skiing, shopping and eating in Aspen Highlands.
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Property Image From US $4,307
         

New
House
Luxury Aspen Retreat– 5 Mins to Town & Slopes, 5BR, Dog Friendly, Holiday Ready!
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens

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Property Image From US $3,942
         

New
Condo
The Ritz-Carlton Club | 3 Bedroom Residence 8206, Ski-in & Ski-out Resort in Aspen Highlands
  • Air Conditioner
  • Parking
  • Pool

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★ Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Aspen Highlands.

Weather in Aspen Highlands

View the weather forecast for Aspen Highlands before booking your Aspen Highlands Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Aspen Highlands, CO

Topwintervacations offers a large selection of top attractions around Aspen Highlands. Research things to do on your vacation before you visit Aspen Highlands.


Aspen Mountain Aspen Snowmass Buttermilk Mountain Maroon Bells Maroon Bells Aspen Skiing Company Silver Queen Gondola Snowmass Mall Summit Express Ski Lift Aspen Recreation Center The John Denver Sanctuary Aspen Art Museum Wagner Park Ski School Magic Carpet Ski Lift Silver Circle Ice Rink Maroon Lake Snowmass Club Ashcroft Ghost Town Krabloonik Dogsled Rides Aspen Golf and Tennis Club