Book Holiday Homes in Winter Park

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Featured Holiday Homes in Winter Park

Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!

Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!

Winter Park
With a stay at this vacation home in Winter Park (Bear Crossing), you'll be within a 15-minute drive of Winter Park Ski Resort and Blue Sky Massage.
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Ski In Out Luxury Condo 2207 I Hot Tub I Gym I Ski Views I Best Price I FREE Adventures Daily

Ski In Out Luxury Condo 2207 I Hot Tub I Gym I Ski Views I Best Price I FREE Adventures Daily

Winter Park
When you stay at this vacation home in Winter Park, you'll be on a river, within a 15-minute walk of Winter Park Ski Resort and The Gondola.
Ski In Out Luxury Condo 2207 I Hot Tub I Gym I Ski Views I Best Price I FREE Adventures Daily
5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle

5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle

Fraser
Located in Winter Park, this vacation home is in the mountains, within a 10-minute drive of Colorado Adventure Park and Fraser Valley Library.
5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle
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Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub.

Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub.

Fraser
Located in Winter Park, this vacation home is in the mountains, within a 10-minute drive of Colorado Adventure Park and Fraser Valley Library.
Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub.
Cozy Chalet with Mountain Views & Large Balcony - Steps to Shuttle

Cozy Chalet with Mountain Views & Large Balcony - Steps to Shuttle

Winter Park
With a stay at this vacation home in Winter Park, you'll be in the mountains, within a 15-minute drive of Winter Park Ski Resort and Blue Sky Massage.
Cozy Chalet with Mountain Views & Large Balcony - Steps to Shuttle
Downtown Townhome w/Free WiFi, Shuttle Service, Private Hot Tub, & Washer/Dryer

Downtown Townhome w/Free WiFi, Shuttle Service, Private Hot Tub, & Washer/Dryer

Winter Park
With a stay at this vacation home in Winter Park, you'll be in the mountains, within a 10-minute drive of Winter Park Ski Resort and Body Kneads Massage and ...
Downtown Townhome w/Free WiFi, Shuttle Service, Private Hot Tub, & Washer/Dryer
Trailhead  524 Clubhouse w/ Hot tub | Pool

Trailhead 524 Clubhouse w/ Hot tub | Pool

Winter Park
With a stay at this vacation home, you'll be centrally located in Winter Park, within a 10-minute drive of Winter Park Ski Resort and Winter Park Visitor ...
Trailhead 524 Clubhouse w/ Hot tub | Pool
216 Sawyer w/ Private Hot Tub

216 Sawyer w/ Private Hot Tub

Winter Park
With a stay at this vacation home in Winter Park, you'll be within a 10-minute drive of Winter Park Ski Resort and Winter Park Visitor Center.
216 Sawyer w/ Private Hot Tub
Spacious Townhome with Private Hot Tub, minutes away from Winter Park Resort

Spacious Townhome with Private Hot Tub, minutes away from Winter Park Resort

Winter Park
With a stay at this vacation home in Winter Park, you'll be in the mountains, within a 10-minute drive of Winter Park Ski Resort and Moffat Tunnel West ...
Spacious Townhome with Private Hot Tub, minutes away from Winter Park Resort
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Winter Park Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winter Park vacation homes are the perfect way for you to wing it.

Holiday houses in Winter Park let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winter Park in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winter Park adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winter Park with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winter Park vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winter Park Holiday Homes essential information

Accommodation
645 Holiday Homes
Lowest Price
AU$292
Highest Price
AU$466
Popular accommodation
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!, Ski In Out Luxury Condo 2207 I Hot Tub I Gym I Ski Views I Best Price I FREE Adventures Daily, 5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle, Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub., Cozy Chalet with Mountain Views & Large Balcony - Steps to Shuttle, Downtown Townhome w/Free WiFi, Shuttle Service, Private Hot Tub, & Washer/Dryer, Trailhead 524 Clubhouse w/ Hot tub | Pool, 216 Sawyer w/ Private Hot Tub, Spacious Townhome with Private Hot Tub, minutes away from Winter Park Resort

Top trending hotels in Winter Park

Winter Park Mountain Lodge

Winter Park Mountain Lodge

3 out of 5
81699 US Highway 40, Winter Park, CO
The price is AU$321 per night from 5 Jan to 6 Jan
AU$321
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Winter Park, Winter Park Mountain Lodge is in the mountains, within a 5-minute drive of Amaze'n Maze Winter Park and Trestle Bike Park.
Winter Park Mountain Lodge
Gravity Haus Winter Park

Gravity Haus Winter Park

3.5 out of 5
78869 US-40, Winter Park, CO
Fully refundableReserve now, pay when you stay
The price is AU$292 per night from 5 Jan to 6 Jan
AU$292
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Gravity Haus Winter Park in Winter Park, you'll be near ski lifts, within a 10-minute drive of Winter Park Ski Resort and Winter Park Visitor ...
Gravity Haus Winter Park
The Vintage Hotel

The Vintage Hotel

3 out of 5
100 Winter Park Dr, Winter Park, CO
The price is AU$466 per night from 24 Dec to 25 Dec
AU$466
includes taxes & fees
24 Dec - 25 Dec
With a stay at The Vintage Hotel in Winter Park, you'll be in the mountains, within a 10-minute drive of Winter Park Ski Resort and Village Cabriolet.
The Vintage Hotel
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Best Western Alpenglo Lodge

Best Western Alpenglo Lodge

2.5 out of 5
78665 US Hwy 40, Winter Park, CO
Fully refundableReserve now, pay when you stay
The price is AU$342 per night from 5 Jan to 6 Jan
AU$342
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Best Western Alpenglo Lodge in Winter Park, you'll be near ski lifts, within a 10-minute drive of Winter Park Ski Resort and Body Kneads Massage ...
Best Western Alpenglo Lodge
Don't see what you're looking for?
See all available properties in Winter Park
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.