Book Holiday Homes in Winter Park

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Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Winter Park

Luxe Downtown Winter Park Private Hot Tub 4 BR

Luxe Downtown Winter Park Private Hot Tub 4 BR

Winter Park
Stay at this vacation home in Winter Park. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Winter Park Ski Resort and Body Kneads ...
Luxe Downtown Winter Park Private Hot Tub 4 BR
Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub.

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

Fraser
Book a stay at this family-friendly vacation home in Winter Park. Enjoy free WiFi, private hot tubs, and a garden. Popular attractions Winter Park Ski Resort ...
Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub.
Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI

Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI

Winter Park
Stay at this vacation home in Winter Park. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Winter Park Ski Resort and Grand Park ...
Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI
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Base Camp 490 Private Hot Tub

Base Camp 490 Private Hot Tub

Winter Park
Book a stay at this ski vacation home in Winter Park. Enjoy free WiFi, ski-in/ski-out access, and patios. Popular attractions Winter Park Ski Resort and Village ...
Base Camp 490 Private Hot Tub
Ranch Creek Lodge | Pet Welcome! | Private Hot Tub | Near Ski Trails

Ranch Creek Lodge | Pet Welcome! | Private Hot Tub | Near Ski Trails

Fraser
Book a stay at this family-friendly lodge in Winter Park. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Winter Park Ski Resort ...
Ranch Creek Lodge | Pet Welcome! | Private Hot Tub | Near Ski Trails
Beautiful 3 Bedroom Townhome In Downtown Winter Park With Private Hot Tub

Beautiful 3 Bedroom Townhome In Downtown Winter Park With Private Hot Tub

Winter Park
Stay at this vacation home in Winter Park. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Winter Park Ski Resort and ...
Beautiful 3 Bedroom Townhome In Downtown Winter Park With Private Hot Tub
Welcoming Modern Ski & Adventure Retreat: Free Ski Resort Shuttle right outside!

Welcoming Modern Ski & Adventure Retreat: Free Ski Resort Shuttle right outside!

2 out of 5
Winter Park
Stay at this vacation home in Fraser. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Winter Park Ski Resort and Grand Park Community ...
Welcoming Modern Ski & Adventure Retreat: Free Ski Resort Shuttle right outside!
Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily

Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily

Winter Park
Book a stay at this family-friendly vacation home in Winter Park. Enjoy free WiFi, a fitness center, and concierge services. Popular attractions Winter Park ...
Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily
Mountain Views | Walk to Downtown & Activities

Mountain Views | Walk to Downtown & Activities

2 out of 5
Winter Park
Book a stay at this family-friendly vacation home in Winter Park. Enjoy free WiFi, a garden, and balconies. Popular attractions Winter Park Ski Resort and Grand ...
Mountain Views | Walk to Downtown & Activities
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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
784 Holiday Homes
Lowest Price
NZ$268
Highest Price
NZ$405
Popular accommodation
Luxe Downtown Winter Park Private Hot Tub 4 BR, Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub., Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI, Base Camp 490 Private Hot Tub, Ranch Creek Lodge | Pet Welcome! | Private Hot Tub | Near Ski Trails, Beautiful 3 Bedroom Townhome In Downtown Winter Park With Private Hot Tub, Welcoming Modern Ski & Adventure Retreat: Free Ski Resort Shuttle right outside!, Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily, Mountain Views | Walk to Downtown & Activities

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 NZ$405 per night from 5 Apr to 6 Apr
NZ$405
includes taxes & fees
5 Apr - 6 Apr
Book a stay at this ski hotel in Winter Park. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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 NZ$296 per night from 14 Apr to 15 Apr
NZ$296
includes taxes & fees
14 Apr - 15 Apr
Stay at this 3.5-star business-friendly hotel in Winter Park. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the bar and the helpful staff ...
Gravity Haus Winter Park
The Vintage Hotel

The Vintage Hotel

3 out of 5
100 Winter Park Dr, Winter Park, CO
The price is NZ$268 per night from 29 Apr to 30 Apr
NZ$268
includes taxes & fees
29 Apr - 30 Apr
Stay at this hotel in Winter Park. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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 NZ$298 per night from 3 Apr to 4 Apr
NZ$298
includes taxes & fees
3 Apr - 4 Apr
Book a stay at this business-friendly hotel in Winter Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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.