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Vacation Rentals & Villas in Winter Park

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259 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

$253

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$180

Zephyr Mountain Lodge Unit 1326 (***********)

Winter Park house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$191

Zephyr Mountain Lodge 2b/2b Sleeps 10 BOGO Ticket

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 52 minutes

Price per night from

$359

Leland Creek Home

Winter Park house

5 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$1,138

Ultra Luxe 7000 Sqft Winter Park Cabin

Winter Park villa

9 bedrooms / 6 bathrooms / sleeps 36

Responds fast! avg. 3 hours 5 minutes

Price per night from

$1,985

Trailhead Lodges 524

Winter Park townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 59 minutes

Price per night from

$184

7 B/7.5 BA Winter Park Amazing views, Huge Kitchen Dining, Family Reunions

Winter Park house

7 bedrooms / 7 bathrooms / sleeps 18

“Amazing Views with Huge Kitchen and Dining for 16” We stayed at Oso's Overlook for Thanksgiving with family and friends. The photos don't do it justice, especially when it comes to the breathtaking views of Indian Peaks out the back and Beyer's Peak out the front! The house is filled with high-end details like luxury bedding, granite, creative lighting and picture windows throughout. The kitchen had two ovens plus loads of cookware, which made cooking the turkey and the pies simultaneously a breeze! We each had our own bedroom and bath. Most of the bedrooms were big enough for an extra twin mattress (supplied), so our toddler could stay in our room with us. The house is on a hill on a big property so when we got a surprise Thanksgiving snowfall, the kids took the sleds (available in the garage of the house) and sledded down the hills for hours. They had a blast! Everyone warmed up by the huge fireplace in the main room. You'll love it!

Price per night from

$772

Trailhead Lodges 812

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 59 minutes

Price per night from

$184

Trailhead Lodges 212

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 59 minutes

Price per night from

$144

Upgraded 1b/1b Sleeps 6 Slopeside

Winter Park condo

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 52 minutes

Price per night from

$276

Hi Country House 1604

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 59 minutes

Price per night from

$103

Hideaway Station Unit TE-405

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 59 minutes

Price per night from

$232

Hideaway Station Unit TS-23

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 59 minutes

Price per night from

$176

Snowblaze A23

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 59 minutes

Price per night from

$119

Arrow 288

Winter Park condo

3 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 59 minutes

Price per night from

$240

Fraser Crossing 3405

Winter Park condo

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 59 minutes

Price per night from

$124

Riverfront Upscale remodel in great location

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$298

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$166

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

/ 1 bathroom / sleeps 4

Price per night from

$166

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

Winter Park house

5 bedrooms / 3 bathrooms / sleeps 19

Price per night from

$524

Spectacular Ski Slope View Condo - Fraser Crossing / Founders Pointe

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$304

Premium Unit 2219 - One Bedroom - Zephyr Mountain Lodge

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 34 minutes

Price per night from

$229

FREE Local Activities! 3 minute walk to Gondola! Prime location in the village

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 7 minutes

Price per night from

$107

Zephyr Mountain Lodge, Condo | 3 Bedroom (Select-Rated Condo 2323)

Winter Park condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$511

Lovely Mountain Adventure Zephyr Mountain Lodge Condo with Ski Storage

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 34 minutes

Price per night from

$364

Great Ski-In/Ski-Out Zephyr Mountain Lodge Condo with Lovely Balcony Views

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$364

Comfortable Fraser Crossing/Founders Pointe Condo with Easy Access to the

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 34 minutes

Price per night from

$278

Fraser Crossing/Founders Pointe, Condo | Gondola Access (Premium-Rated Condo

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 39 minutes

Price per night from

$208

Great Zephyr Mountain Lodge Condo with Village & Continental Divide Views

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$364

Zephyr Mountain Lodge, Condo | 2 Bedroom (Select-Rated Condo 1615)

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$364

Select Unit 1323 - Two Bedroom - Zephyr Mountain Lodge (Select-Rated Condo 1323)

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$364

Zephyr Mountain Lodge, Condo | Ski Slope View (Select-Rated Condo 2209)

Winter Park condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$578

Bear Trail Home

Winter Park house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 59 minutes

Price per night from

$311

Select Unit 4185 - Two Bedroom - Fraser Crossing/Founders Pointe

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 39 minutes

Price per night from

$315

Pool & Hot Tub | Views from Top Floor | Downtown BV 16-31

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 7 minutes

Price per night from

$107

Select Unit 1316 - Two Bedroom - Zephyr Mountain Lodge (Select-Rated Condo 1316)

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$364

WINTER PARK PET FRIENDLY | POOL & HOT TUB | SHUTTLE TO RESORT

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 7 minutes

Price per night from

$190

Viewing 38 of 259
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.

Top Destination reviews

Beautiful Mountain House - Luxury in a Rustic Mountain Setting
Reunion Weekend Getaway

We loved staying in this beautiful mountain home for a Law School Reunion Weekend Getaway with many friends! The location is picturesque and the house well-stocked, clean, comfortable, luxurious, and now home to a great memory held by all who came. We will be back! Thank you to the wonderful Kelleys.see more
3 bedroom mountain home in Winter Park Colorado
Great rental

We stayed at this property for a spring family ski trip and it was perfect for our family. The kids loved the cozy bunk beds and being able to play in the yard and have their own space in the back den, and our teenager (and friend) enjoyed being able to walk to town and the park nearby. Big TV in the living room. Fantastic hot tub both daytime and with the snow falling at night. Kitchen had everything we needed for a big group. Definitely will stay here again for future ski trips and maybe even this summer.see more
7 B/7.5 BA Winter Park Amazing views, Huge Kitchen Dining, Family Reunions
A Real Gem

Trust me when I say, the pictures don't do this place justice. I actually had my entire wedding on the property. We had most of our guests stay in the house, and the during the entire stay I kept getting asked, "How did you find this place?!" The views are breath-taking. The house is breath-taking. The property is breath-taking. The rooms are very luxurious. You will love your stay here.see more
Charming Log Cabin w/Hot Tub, Deck, Ping Pong,Wifi
"Perfect in every way"

The cabin far exceeded our expectations, from the minute we walked in the door. "Perfect" location, decor & ammenities. My favorite was the huge back deck. Unfortunately we could only stay two nights, we will for sure be returning for a longer stay. I would highly recommend this cabin for families or a Romantic getaway.see more

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