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Vacation Rentals & Villas in Winter Park

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493 villas

Winter Park Condo w/Hot Tub & Shuttle-Walk to Town

Winter Park apartment

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 46 minutes

Price per night from

$228

Winter Park Home w/Ski Hill Views, Sauna & Hot Tub

Winter Park house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 46 minutes

Price per night from

$379

Ski-In/Ski-Out Winter Park Condo w/Resort Hot Tubs

Winter Park apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$101

Cozy Updated Condo With Great Views

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$205

Cozy Winter Park Condo w/Shuttle & Hot Tub Access!

Winter Park apartment

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 46 minutes

Price per night from

$138

Beautiful Mountain House - Luxury in a Rustic Mountain Setting

Winter Park house

4 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$451

Winter Park Condo w/ Hot Tubs, 3 Mi to Ski Resort!

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 46 minutes

Price per night from

$149

Large Luxurious Home,Wooded,Close town Slps16-24

Winter Park house

6 bedrooms / 4 bathrooms / sleeps 24

Price per night from

$510

Custom High-End Mountain Home: Wooded Area, Close to Town Sleeps 16-20

Winter Park house

6 bedrooms / 4 bathrooms / sleeps 20

Price per night from

$862

Luxe Cabin: 2 King Master Suites on Shuttle Route

Winter Park house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 46 minutes

Price per night from

$311

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

New 4-Bedroom 4-Bath Family Cabin - Walk to Bus!

Winter Park log cabin

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 46 minutes

Price per night from

$374

9,000 square foot, 9 Bedroom, 9 bath, Victorian Style property for rent.

Winter Park house

9 bedrooms / 9 bathrooms / sleeps 28

“Great! Great Food! Great Hosts! Great Location!” My husband and I stayed at the Winter Park Chateau to celebrate our anniversary. We were pleasantly surprised by a bouquet of flowers and champagne in our room upon arrival. Very thoughtful. We enjoyed social hour treats and wine by the fireplace before we walked across the street for a great dinner. So nice to not to have to drive! We will be back again for our next anniversary for sure!!!

Price per night from

$1,216

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$184

Winter Park Cabin - Walk to Main Street & Downtown

Winter Park log cabin

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 46 minutes

Price per night from

$166

New listing! Charming & cozy cabin with private hot tub and mountain views

Winter Park house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$335

Family-friendly condo w/ bikes, fireplace - near skiing and Main Street!

Winter Park house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$245

8+ Bedroom Home is Heart of Winter Park, On shuttle route, sleeps 24+

Winter Park house

9 bedrooms / 6 bathrooms / sleeps 30

Price per night from

$1,734

Rustic Luxury, Unobstructed Views

Winter Park log cabin

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 19 minutes

Price per night from

$571

Snowblaze E113

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 0 minutes

Price per night from

$109

Newly Remodeled Studio/Think Snow!

Winter Park studio

Studio / 1 bathroom / sleeps 3

Price per night from

$229

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

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 57 minutes

Price per night from

$200

Ultra Luxe 7000 Sqft Winter Park Cabin

Winter Park villa

9 bedrooms / 6 bathrooms / sleeps 36

Price per night from

$2,028

Winter Park Condo w/Deck & Grill-Walk to Main St!

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Price per night from

$226

Winter Park Condo on Bus Route, 2 Blocks to Dtwn!

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 46 minutes

Price per night from

$131

Trailhead Lodges 524

Winter Park townhouse

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 0 minutes

Price per night from

$231

Downtown Winter Park Townhouse 3 Mi to Ski Resort!

Winter Park townhouse

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 46 minutes

Price per night from

$250

Cozy Winter Park Condo w/ Patio - Walk to Main St!

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 46 minutes

Price per night from

$178

Mountain-View Townhome w/ Balconies, Private Hot Tub & Three Levels

Winter Park townhouse

3 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$181

Ski-In/Out Zephyr Mtn Lodge Condo w/Hot Tub Access

Winter Park apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 46 minutes

Price per night from

$237

Winter Park Area Family Cabin w/Mtn View & Hot Tub

Winter Park house

3 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 46 minutes

Price per night from

$243

Luxurious Cabin: Two Master Suites, Hot tub, Views

Winter Park house

4 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$440

Cozy Winter Park Studio w/Views-Walk to Downtown!

Winter Park studio

Studio / 1 bathroom / sleeps 6

Responds fast! avg. 46 minutes

Price per night from

$91

7 B/7.5 BA Winter Park Amazing views, 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

$804

Fraser Home w/Mtn. Views - 10 Min. to Winter Park!

Winter Park house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 46 minutes

Price per night from

$267

Cozy Winter Park Condo w/ Hot Tub & Shuttle!

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 46 minutes

Price per night from

$96

NEW! Cozy Ski Condo w/Hot Tubs, 3 Mi to WP Resort!

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 46 minutes

Price per night from

$91

Front-Row Ski Slope Views | Antlers at Lakota Luxe Living | Private Hot Tub

Winter Park townhouse

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$233

Viewing 38 of 493
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

Winter Park Condo w/ Hot Tubs, 3 Mi to Ski Resort!
Cozy Comfortable Condo

The location of this condo was excellent, walking distance to WinterPark downtown (10-15 min). Very easy to locate. The condo was very updated, nice size bedrooms and comfortable beds. The condo was clean with nice furnishings and everything you need in the kitchen. I loved the wall mirror in the dining area. The condo is small and would not recommend it for a huge group even though it sleeps 7, however it is very nice for a small group. The area was quite and clean and the owner was very pleasant to deal with.see more
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, 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
Luxurious Cabin: Two Master Suites, Hot tub, Views
Beautiful, spacious home

This beautiful home was perfect for our extended family! We had a baby with us, so the baby gates, high chair and portable crib were great! Wonderful space to gather and play games and be together, plus room to spread out and have some privacy as well. Lacey and Lee were very accommodating and took care of any needs we had. We will be back!see more

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