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Holiday homes in Winter Park You’ll Love

Top-Rated Winter Park Holiday homes for Every Budget and Style!

Looking for a holiday home in Winter Park (Colorado)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $55.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Winter Park.

We found 341 Holiday-homes in Winter Park and the surrounding area (within 20 miles)

Luxury Modern Tiny Home in Downtown Fraser in Fraser, USA

Luxury Modern Tiny Home in Downtown Fras...

Villa in Fraser near Winter Park, Colorado , 204 Byers Avenue
With garden views, this accommodation offers a balcony.
  • Parking

no reviews

from $247.32 Show details »

Custom Ski In Ski Out Luxury Chalet 239 - Hot Tub & Amazing Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

Custom Ski In Ski Out Luxury Chalet 239...

Holiday home in Winter Park, Colorado
Featuring barbecue facilities, Custom Ski In Ski Out Luxury Chalet 239 - Hot Tub & Amazing Views - 500 Dollars Of FREE Activities & Equipment Rentals ...
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Spa and wellness centre

Exceptional 1 Reviews 10.0

from $73.00 Show details »

Ski In Out Luxury Chalet With Hot Tub, Pool Table & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

Ski In Out Luxury Chalet With Hot Tub, P...

Holiday home in Winter Park, Colorado
Among the facilities of this property are a restaurant, a 24-hour front desk, and a concierge service, along with free Wifi throughout the property.
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Fitness centre

Exceptional 1 Reviews 10.0

from $1.068.08 Show details »

Base Camp 496 in Winter Park, USA

Base Camp 496

Holiday home in Winter Park, Colorado
This vacation home features accommodations with a patio.
  • Parking

no reviews

from $1.026.50 Show details »

New Ski In Out Luxury Loft #103 - Hot Tub, Gym, Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

New Ski In Out Luxury Loft #103 - Hot Tu...

Holiday home in Winter Park, Colorado , 422 Iron Horse Way #103
Among the facilities of this property are a restaurant, a 24-hour front desk, and an elevator, along with free Wifi throughout the property.
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Fitness centre

no reviews

from $420.24 Show details »

New Ski In Out Luxury Loft #201 With Hot Tub, Gym & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

New Ski In Out Luxury Loft #201 With Hot...

Holiday home in Winter Park, Colorado
The vacation home offers a spa experience, with its hot tub, wellness packages, and fitness room.
  • Parking
  • Bar
  • Sauna
  • Fitness centre
  • Family rooms

Exceptional 2 Reviews 10.0

from $413.56 Show details »

Ski & Chill in Winter Park, USA

Ski & Chill

Holiday home in Winter Park, Colorado , 422 Iron Horse Way, Unit 202
This property offers access to a balcony, free private parking, and free Wifi.
  • Parking

no reviews

from $272.19 Show details »

Ski In Out Luxury Condo #4657 With Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

Ski In Out Luxury Condo #4657 With Huge...

Holiday home in Winter Park, Colorado
Among the facilities of this property are a restaurant, a 24-hour front desk, and an elevator, along with free Wifi throughout the property.
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Fitness centre

Good 8 Reviews 7.3

from $218.89 Show details »

Ski In-Out Luxury Condo #4474 With Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

Ski In-Out Luxury Condo #4474 With Huge...

Holiday home in Winter Park, Colorado
A fitness room is available for guests.
  • Sauna
  • Fitness centre
  • Family rooms
  • Spa and wellness centre
  • Indoor pool

Good 8 Reviews 7.6

from $273.56 Show details »

Ski In-Out Luxury Condo #4283 With Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

Ski In-Out Luxury Condo #4283 With Huge...

Holiday home in Winter Park, Colorado
With lake views, this accommodation provides a patio.
  • Parking
  • Bar
  • Sauna
  • Fitness centre
  • Family rooms

Very good 5 Reviews 8.4

from $279.86 Show details »

Ski In Ski Out Luxury Condo #4574 - Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

Ski In Ski Out Luxury Condo #4574 - Huge...

Holiday home in Winter Park, Colorado
Offering barbecue facilities, Ski In Ski Out Luxury Condo #4574 - Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Dail...
  • Parking
  • Bar
  • Sauna
  • Fitness centre
  • Family rooms

Superb 13 Reviews 9.1

from $215.50 Show details »

Ski In Out Luxury Condo #4454 With Huge Hot Tub & Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

Ski In Out Luxury Condo #4454 With Huge...

Holiday home in Winter Park, Colorado , 580 Winter Park Dr. #4454
Featuring barbecue facilities, Ski In Out Luxury Condo #4454 With Huge Hot Tub & Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily feat...
  • Parking
  • Bar
  • Sauna
  • Fitness centre
  • Family rooms

Exceptional 1 Reviews 10.0

from $286.38 Show details »

Zephyr Mountain Lodge 1417 - Ski In Ski Out Condo in Winter Park, USA

Zephyr Mountain Lodge 1417 - Ski In Ski...

Holiday home in Winter Park, Colorado
Among the facilities at this property are a 24-hour front desk and an elevator, along with free Wifi throughout the property.
  • Parking
  • Fitness centre

no reviews

from $50.00 Show details »

Ski In-Out Luxury Condo #4375 With Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

Ski In-Out Luxury Condo #4375 With Huge...

Holiday home in Winter Park, Colorado
Offering barbecue facilities, Ski In-Out Luxury Condo #4375 With Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily...
  • Parking
  • Bar
  • Sauna
  • Fitness centre
  • Family rooms

Pleasant 3 Reviews 6.7

from $279.86 Show details »

Zephyr Mountain Lodge 1318 - Ski In Ski Out Condo in Winter Park, USA

Zephyr Mountain Lodge 1318 - Ski In Ski...

Holiday home in Winter Park, Colorado
With mountain views, this accommodation provides a terrace.
  • Parking
  • Fitness centre

no reviews

from $55.00 Show details »

Zephyr Mountain Lodge 1601 - 2 Bedroom Ski In Ski Out Condo in Winter Park, USA

Zephyr Mountain Lodge 1601 - 2 Bedroom S...

Holiday home in Winter Park, Colorado
With mountain views, this accommodation offers a balcony.
  • Parking
  • Fitness centre

no reviews

from $60.00 Show details »

Zephyr Mountain Lodge 1508 - Ski In Ski Out Condo in Winter Park, USA

Zephyr Mountain Lodge 1508 - Ski In Ski...

Holiday home in Winter Park, Colorado
With mountain views, this accommodation offers a balcony.
  • Parking
  • Fitness centre

no reviews

from $67.00 Show details »

Zephyr Mountain Lodge 1218 - Ski In Ski Out Condo in Winter Park, USA

Zephyr Mountain Lodge 1218 - Ski In Ski...

Holiday home in Winter Park, Colorado
Free Wifi is available throughout the property and private parking is available on site.
  • Parking
  • Fitness centre

no reviews

from $93.00 Show details »

Zephyr Mountain Lodge 1303 - Ski In Ski Out Condo in Winter Park, USA

Zephyr Mountain Lodge 1303 - Ski In Ski...

Holiday home in Winter Park, Colorado
Complimentary Wifi is provided throughout the property and private parking is available on site.
  • Parking
  • Fitness centre

no reviews

from $96.00 Show details »

Zephyr Mountain Lodge 1215 - Ski In Ski Out Condo in Winter Park, USA

Zephyr Mountain Lodge 1215 - Ski In Ski...

Holiday home in Winter Park, Colorado
Free Wifi is featured throughout the property and private parking is available on site.
  • Parking
  • Fitness centre

no reviews

from $100.00 Show details »

Zephyr Mountain Lodge 1606 - 2 Bedroom Ski In Ski Out Condo in Winter Park, USA

Zephyr Mountain Lodge 1606 - 2 Bedroom S...

Holiday home in Winter Park, Colorado
With mountain views, this accommodation features a terrace.
  • Parking
  • Fitness centre

Very good 1 Reviews 8.0

from $78.00 Show details »

Ski In Out Luxury Penthouse #1706 With Hot Tub & Great Views - 500 Dollars Of FREE Activities And Equipment Rentals Daily in Winter Park, USA

Ski In Out Luxury Penthouse #1706 With H...

Holiday home in Winter Park, Colorado
Among the facilities of this property are a restaurant, a 24-hour front desk, and an elevator, along with free Wifi throughout the property.
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Fitness centre

Exceptional 1 Reviews 10.0

from $394.25 Show details »

Ski In Out Luxury Penthouse #1703 With Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily in Winter Park, USA

Ski In Out Luxury Penthouse #1703 With H...

Holiday home in Winter Park, Colorado
Among the facilities of this property are a restaurant, a 24-hour front desk, and an elevator, along with free Wifi throughout the property.
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Fitness centre

Good 5 Reviews 7.6

from $476.92 Show details »

Founders Pointe Condo in Winter Park, USA

Founders Pointe Condo

Holiday home in Winter Park, Colorado
Both parking on-site and free Wifi are accessible at Founders Pointe Condo.
  • Parking

Good 13 Reviews 7.7

from $161.33 Show details »

Ski In Out Luxury Condo 2207 - Hot Tub - Gym - Ski Views - Best Price - 500 dollars in FREE Activities and Equipment Rentals Daily in Winter Park, USA

Ski In Out Luxury Condo 2207 - Hot Tub -...

Holiday home in Winter Park, Colorado
Free Wifi is offered throughout the property and private parking is available on site.
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Spa and wellness centre

Fabulous 1 Reviews 9.0

from $311.04 Show details »

Number of Holiday homes in Winter Park 341
Number of guest ratings 2,516
Average price per night $283.00
Lowest price per night $55,00
Highest price per night $1.039,54

Top 10 Cheapest Holiday-homes in Winter Park

Discover the Cheapest Holiday-homes in Winter Park – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Winter Park

Check out the Most Booked Holiday-homes in Winter Park – Based on Guest Popularity.

Holiday homes in Winter Park (Colorado), comfortable and familiar

Staying in a holiday or vacation home in Winter Park can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Winter Park for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Winter Park should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com