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Oregon Trail

8 guests · 4 bedrooms · 4.5 bathrooms
A five-minute stroll from Tiehack ski lift and ten minutes from downtown, this trendy ski lodge enjoys a scenic location just on the edge of the hustle and bustle of Aspen. With four king ensuite bedrooms and shared access to the Caribou Club amenities, Oregon Trail is the perfect destination for a family ski trip, couples retreat, or special occasion. Nearby, you’ll find numerous ski access points, golf courses, and some of Colorado’s most charming shops and boutiques.
From the outside, Oregon Trail shows off iconic chalet design with its peaked roof, imposing timbre frame, and natural stonework. Inside, the villa takes an elegant turn, utilizing pure-white tones, deep marble, and designer furnishings to provide the perfect contrast to Aspen’s rugged terrain. The spacious living room is a great spot for group gatherings, with more than enough comfortable seating for everyone to warm up around the fireplace. In the kitchen, you’ll appreciate the state of the art appliances and a very generous working layout. At dinner, you’ll appreciate the formal dining area, with seating for ten. And, in the warmer months, the terrace has an alfresco set with space for five.
After a long day on the slopes, Oregon Trail’s hot tub is the perfect place to relax and rejuvenate for an exciting evening. If you’re in the mood for a quiet evening, get a fire going and settle in for a movie night with the family. If the group is feeling rowdy, the Caribou Club has a great restaurant, bar, and nightclub on-site.
During your stay, you’ll have easy ski access at Buttermilk Mountian, Aspen Highlands, Aspen Mountain, and Snowmass Village. In the summer, Aspen’s golf courses offer incredible mountain views and challenging fairways. And, you’ll find a wide range of restaurants, bars, and shops in downtown Aspen, a city that remains vibrant all year round.
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  • Bedroom 1 - Master: King size bed, Ensuite bathroom with stand-alone steam shower & bathtub, Dual vanity, Walk-in closet, Fireplace, Television, Direct access to terrace
  • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Dual vanity, Television 
  • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower
  • Bedroom 4: King size bed, Queen sleeper sofa, Ensuite bathroom with stand-alone shower, Television 
  • Fully equipped kitchen with breakfast bar
  • Dishwasher
  • Wine fridge
  • Formal dining area with seating for 10
  • Cable television 
  • Gas fireplace
  • Wi-Fi
  • Air conditioning 
  • Heating
  • Elevator
  • Washer/Dryer
  • Iron/Ironing board
  • Hot tub - Heating included 
  • Alfresco dining with seating for 5 
  • Garage - 1 space
  • Parking - 1 space
  • Terrace 
  • Barbeque
  • Housekeeping Service - Trash & Tidy Service provided every 3 days for reservations 5 nights or longer. Linen change not included.
  • Limited access to on-site host services (1 reservation per day)
Extra cost (advance notice may be required):
  • Additional housekeeping
  • Villa pre-stocking
  • Airport transfer
  • Activities and excursions
Extra cost:
  • Restaurant
  • Bar
  • Night club
  • Lounge 
Points of Interest
  • 6 minute drive to Aspen Golf & Tennis Club
  • 9 minute drive to Aspen Highlands Village
  • 10 minute drive to Downtown Aspen
  • 6.3 miles to Snowmass Club Golf Course 
  • 6.9 miles to Snowmass Village
Ski Access
  • 5 minute walk to the base of Tiehack lift at Buttermilk
  • 7 minute drive to Buttermilk Mountain
  • 9 minute drive to Aspen Highlands Mountain
  • 3.8 miles to Aspen Mountain
  • 6.9 miles to Snowmass Village
  • 8 minute drive to Aspen-Pitkin Airport (ASE)
  • 67 miles to Eagle County Regional Airport (EGE)
  • 219 miles to Denver International Airport (DEN)
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Dining area for 5 people
BBQ grill
Hot tub
Gas fireplace
Breakfast bar
Wine storage
Chef's kitchen
Sound system
Air conditioning
Washing machine
Garage parking
+ 3 more
Lounge area
Aspen, CO
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Cancellation Policy and House Rules
Cancel up to 95 days before your trip and get a full refund. Cancel within 95 days of the trip and the reservation is non-refundable.