Book Holiday Homes in Winter Park

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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
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 Body Kneads Massage and ...
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
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.
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
With a stay at this vacation home in Winter Park, you'll be within a 15-minute drive of Winter Park Ski Resort and Grand Park Community Recreation Center.
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
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 The Gondola.
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
Located in Winter Park, this lodge is in the mountains, within a 10-minute drive of Fraser Valley Library and Colorado Adventure Park.
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
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.
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
With a stay at this vacation home, you'll be centrally located in Fraser, within a 15-minute drive of Winter Park Ski Resort and Cozens Ranch House Museum.
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
With a stay at this vacation home, you'll be centrally located in Winter Park, within a 15-minute drive of Winter Park Ski Resort and Body Kneads Massage and ...
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
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 Grand Park Community Recreation ...
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
798 Holiday Homes
Lowest Price
AU$244
Highest Price
AU$335
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 AU$335 per night from 10 Apr to 11 Apr
AU$335
includes taxes & fees
10 Apr - 11 Apr
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$268 per night from 15 Apr to 16 Apr
AU$268
includes taxes & fees
15 Apr - 16 Apr
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$244 per night from 21 Apr to 22 Apr
AU$244
includes taxes & fees
21 Apr - 22 Apr
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
Save an average of 15% on thousands of hotels when you're signed in
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$269 per night from 14 Apr to 15 Apr
AU$269
includes taxes & fees
14 Apr - 15 Apr
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.