Vacation Rentals & Villas in Winter Park

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169 villas

Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$259

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$185

Ultra Luxe 7000 Sqft Winter Park Cabin

Winter Park villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 36

Price per night from

$2,877

Trailhead Lodges 524

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$208

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$148

Trailhead Lodges 212

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$133

Hideaway Station Unit TE-405

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$222

Hideaway Station Unit TS-23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$208

Snowblaze A23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$118

Arrow 288

Winter Park condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$251

Fraser Crossing 3405

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Price per night from

$135

Riverfront Upscale remodel in great location

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$305

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$173

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

Price per night from

$173

Beautiful Mountain Lodge-Ski, Hike, Bike, Relax..

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

Price per night from

$576

Ski-in/Ski-out Bliss: Your Dream Getaway near Gondola at Winter Park Resort

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

Price per night from

$204

Cozy Retreat with Private Hot Tub | Spacious Winter Haven near Downtown Winter

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

Price per night from

$277

Downtown Wooded Mountain Setting! Next to Wolf Park on FREE Shuttle. Tim

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

Price per night from

$228

Cozy 2 bed 2 bath Winter Park Mountain Cabin

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$144

Luxury Mountain Haven! Family-Friendly, Ski, Bike, Hike, and Hot-Tub!

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$231

Winter Wonderland: Hot Tub Getaway in Grand Park with Heated Garage

Winter Park house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 2 hours 32 minutes

Price per night from

$349

Quick & Easy Access to the Gondola at Winter Park Resort

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 32 minutes

Price per night from

$156

Alpine Hideaway: Private Hot Tub in Ideal Mountain Haus, 10-Min Shuttle to

Winter Park townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

Price per night from

$409

NEW High-Altitude Hideaway at Lakota Townhomes

Winter Park house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

Price per night from

$965

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Price per night from

$216

Hideaway Park Gem: Ski Shuttle, Pool, and Mountain Views

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 32 minutes

Price per night from

$143

Mountain Majesty: Panoramic Views, Hot Tub, and Easy Access to Shuttle Route!

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

Price per night from

$264

Base Camp 490

Winter Park condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 11

Price per night from

$519

Summer Oasis with Spectacular Views of Winter Park Resort & Private Hot Tub

Winter Park townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Price per night from

$336

Modern Comfort in the Heart of Winter Park with Resort Shuttle

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 32 minutes

Price per night from

$167

Quiet Mountainside Townhome | Private Hot Tub | Close to Mountain Biking

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 32 minutes

Price per night from

$361

Rustic Charm and Urban Comforts: Winter Park Cabin with Hot Tub and Wildlife

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Price per night from

$312

Zephyr Mountain Lodge Slopeside 1420

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$210

Luxury in Downtown Winter Park CO

Winter Park townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 9 minutes

Price per night from

$304

Timber Fox 1403

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$148

Alpine Charm in Downtown Winter Park - Views Included, Steps to Everything

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Price per night from

$312

Summertime Splendor: Mountainside Haven Hot Tub Oasis!

Winter Park townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 2 hours 32 minutes

Price per night from

$481

Riverside Sanctuary: Old Town Winter Park

Winter Park condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Price per night from

$240

Viewing 38 of 169
rentals in Winter Park

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About Winter Park

There are few places in the world that can rival Winter Park, Colorado, for beauty and pristine nature. For skiers, snowboarders, and sight seeking travelers alike, the marvel of the Rockies can become your backyard while staying in your very own vacation home. Pursue outdoor adventures by day and step back inside your rental home at night, the perfect place to enjoy a chili cookout with friends and family. Vacation homes in Winter Park can provide a refreshing alternative to the constrictions and hassles of hotels.

Offering only the very best, Winter Park's world-class ski slopes attract skiers of all skill levels. Voted the number one resort by in-state skiers, Winter Park Ski Resort is known as "Colorado's Favorite," and claims an average annual snowfall of 350 inches per year. Winter Park offers activities not just for winter, but for all seasons. Though skiing may feel like the pinnacle of all Winter Park, Colorado, activity, there is an incredible amount to see and do here all year long. For example, you can hike beautiful mountain trails, bike ride through the city, or horseback ride along the water.

Here are a few additional suggestions as you plan your trip:

  • Experience the Winter Park Music Festival: This annual event offers a summer concert season that begins in the middle of July. Mix it up with the JVC Jazz Festival, offering a blend of funk, soul, and of course, jazz.
  • See a live theater production: Live performances and theatrical productions take place every summer from mid-June to August.
  • Take part in the race: Downhill skiing is not the only option for Colorado travelers. The Grand Lake, 25 miles from Winter Park, is home to fabulous cross country skiing and a Classic Cross Country Skiing Race in March.
  • See Winter Park from above: Take flight in a Great Adventure Balloon Tour, located just one hour from Denver, and view the Rocky Mountain Park in an unforgettable way.
  • Meet world class dog sledding teams: During Winter Park's annual dog sled races, teams of dogs pull sleds along an 8 mile track. These races are popular with spectators because of the opportunity to interact with both the dogs and the mushers.
  • Hike the trails: Go hiking, biking, or Winter Park snowmobiling through the Apache National Forest. Straddling the continental divide in north central Colorado, the forest represents the quiet side of Rocky Mountain National Park.

Snowboard and ski Winter Park's slopes during the cold season, and come back in the spring to see the mountains bloom with wildflowers. No matter when you choose to schedule your visit, experience the beauty of the Rocky Mountains from your own private luxury vacation rental. Rent a trendy condo close to the shopping and nightlife downtown, or find a secluded lakeside cabin with all the amenities you and your family need for the perfect vacation adventure. While you're visiting Winter Park, you may also want to explore beautiful nearby mountain destinations like Vail and Telluride.

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