Luxury Vacation Rentals in Winter Park

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 348 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Winter Park

Luxury

Meadow Glade Pond Chalet 13

4 bedrooms•4 baths

•

~$140 less than other sites

Luxury

Bridgers Cache Ski In/Out Chalet 277

4 bedrooms•4.5 baths

•

~$210 less than other sites

Luxury

Meadow Glade Pond Chalet 9

4 bedrooms•4 baths

•

~$185 less than other sites

Slopeside Trademark Villa 90

3 bedrooms•3 baths

•

~$80 less than other sites

Founders Pointe Ski In/Out Penthouse 4657

2 bedrooms•2 baths

•

~$55 less than other sites

Chill Ski In/Out Condo 102

3 bedrooms•2 baths

•

~$80 less than other sites

Timber Lake 341

3 bedrooms•3.5 baths

•

New

~$105 less than other sites

Bear Trail Villa 865

3 bedrooms•3.5 baths

•

~$95 less than other sites

Welcome to Winter Park

Step into elevated mountain living with Wander's collection of luxury vacation rentals in Winter Park. Our homes pair the polish of a five-star stay with the privacy of a modern alpine retreat, so every moment feels effortless.

Expect bright, contemporary interiors, picture-window views of rugged peaks, plush bedrooms, chef-worthy kitchens, and spa-inspired baths. Ultra fast WiFi, smart tech, and thoughtfully designed work nooks make it easy to mix meetings with mountain time. Every stay includes hotel-grade amenities, inspiring mountain views, meticulous cleaning, and 24/7 concierge service.

Destinations near Winter Park

Available soon in Winter Park

Luxury

Meadow Glade Pond Chalet 13

4 bedrooms•4 baths

•

~$140 less than other sites

Luxury

Bridgers Cache Ski In/Out Chalet 277

4 bedrooms•4.5 baths

•

~$210 less than other sites

Luxury

Meadow Glade Pond Chalet 9

4 bedrooms•4 baths

•

~$185 less than other sites

Slopeside Trademark Villa 90

3 bedrooms•3 baths

•

~$80 less than other sites

Founders Pointe Ski In/Out Penthouse 4657

2 bedrooms•2 baths

•

~$55 less than other sites

Chill Ski In/Out Condo 102

3 bedrooms•2 baths

•

~$80 less than other sites

Timber Lake 341

3 bedrooms•3.5 baths

•

New

~$105 less than other sites

Bear Trail Villa 865

3 bedrooms•3.5 baths

•

~$95 less than other sites

Featured vacation rentals in Winter Park

Timber Top Lodge Home

5 bedrooms•4.5 baths

•

~$220 less than other sites

Winter Park Ski Haus

6 bedrooms•6.5 baths

•

New

~$235 less than other sites

Luxury

Bridgers Cache Ski In/Out Chalet 275

4 bedrooms•3.5 baths

Luxury

Roam River Mansion

5 bedrooms•5 baths

•

~$275 less than other sites

Luxury

Roam River Villa

4 bedrooms•4.5 baths

•

New

~$255 less than other sites

Luxury

Lakota Trail Villa 2225

6 bedrooms•4.5 baths

•

~$245 less than other sites

Lakota Arrow Trail Villa 960

4 bedrooms•3.5 baths

•

~$275 less than other sites

Luxury

Ski Hard/Unwind Harder. Custom Estate/Private Acre

6 bedrooms•4.5 baths

•

New

~$305 less than other sites

Highlights in Winter Park

Discover a year-round mountain playground, offering world-class skiing in winter and thrilling biking and hiking adventures in the summer.

Winter Park Resort

Trestle Bike Park

Fraser River Trail

Berthoud Pass

Devil's Thumb Ranch Resort & Spa

Grand Park Community Recreation Center

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Winter Park

Luxury

Meadow Glade Pond Chalet 13

4 bedrooms•4 baths

•

~$140 less than other sites

Luxury

Bridgers Cache Ski In/Out Chalet 277

4 bedrooms•4.5 baths

•

~$210 less than other sites

Luxury

Meadow Glade Pond Chalet 9

4 bedrooms•4 baths

•

~$185 less than other sites

Slopeside Trademark Villa 90

3 bedrooms•3 baths

•

~$80 less than other sites

Founders Pointe Ski In/Out Penthouse 4657

2 bedrooms•2 baths

•

~$55 less than other sites

Chill Ski In/Out Condo 102

3 bedrooms•2 baths

•

~$80 less than other sites

Timber Lake 341

3 bedrooms•3.5 baths

•

New

~$105 less than other sites

Bear Trail Villa 865

3 bedrooms•3.5 baths

•

~$95 less than other sites

View all homes

Most popular amenities for vacation rentals in Winter Park

Other popular amenities & vacation types in Winter Park

Family vacation rentals in Winter Park

Large group vacation rentals in Winter Park

Pet-friendly vacation rentals in Winter Park

Hot tub vacation rentals in Winter Park

Discover more of Winter Park

Winter Park delivers big-mountain energy with a laid-back Colorado soul. Snow comes early and lingers late across Mary Jane's legendary bumps, wide-open bowls, and sheltered glades. When the thaw arrives, Trestle Bike Park, high-country singletrack, and wildflower basins take center stage along the Continental Divide.

Getting here is part of the fun, from the scenic run over Berthoud Pass to the seasonal Winter Park Express that glides straight through the Moffat Tunnel to the base. Evenings bring alpenglow, starry skies, and the easy pace of a true mountain town. This is why Wander's luxury vacation rentals in Winter Park are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Winter Park

Why should I book a Wander in Winter Park over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Winter Park delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Winter Park?

Some of our most popular vacation rentals in Winter Park include Meadow Glade Pond Chalet 13, Bridgers Cache Ski In/Out Chalet 277, and Meadow Glade Pond Chalet 9. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Winter Park?

Wander offers 348 vacation rentals in Winter Park, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Winter Park?

You can check-in to Wander vacation rentals in Winter Park after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Winter Park have WiFi access?

Yes. Every Wander home in Winter Park has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.