Winter Park holiday lettings

We found 1,984 holiday rentals — enter your dates for availability

Select from 533 houses, 946 flats and other holiday rentals to find the perfect place for your stay in Winter Park. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Winter Park

Showing deals for:10 Oct - 17 Oct
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Why visit Winter Park

  • World-class skiing: Winter Park boasts exceptional ski slopes, perfect for both novice and experienced skiers, making it a winter sports haven.
  • Scenic beauty: The breathtaking landscapes and picturesque lakes provide stunning backdrops for outdoor activities year-round.
  • Charming accommodation: Options range from cosy cabins to stylish condos, ensuring a comfortable stay for every traveller.
  • Adventure activities: Beyond skiing, visitors can enjoy hiking, mountain biking, and other thrilling pursuits in the great outdoors.
  • Rich cultural experiences: Explore local museums and historic railways, adding a cultural twist to your adventure.

Popular types of accommodation in Winter Park

If you're wondering about the types of accommodation available in Winter Park, worry not—we have you sorted. The most popular options for your stay include charming condos, private holiday homes, and rustic cabins. Whether you're searching for winter lodgings or holiday rentals, Winter Park offers a variety of vacation rentals to suit every traveller's needs. Embrace the beauty of this stunning destination with the perfect base for your adventures.

  • Condos: The top choice for holidaymakers in Winter Park, offering modern amenities and convenient access to local attractions.
  • Houses: A fantastic option for families or groups, providing spacious accommodations and a homely atmosphere.
  • Cabins: Ideal for those seeking a rustic escape, these charming lodgings enhance your mountain experience.
  • Apartments: A practical choice for solo travellers or couples, often situated in vibrant areas close to amenities.
  • Chalets: A delightful option that combines traditional style with comfort, perfect for enjoying the scenic surroundings.**

Top attractions in and around Winter Park

Winter Park, Colorado, is an ideal destination for skiing and adventure sports, offering a blend of outdoor activities and cultural experiences. Visitors can explore picturesque lakes, historic railways, and local museums. Take advantage of the Winter Park Escapes and immerse yourself in the Winter Park Experience, particularly during the winter months for skiing. This charming location caters to those seeking both scenic beauty and thrilling outdoor pursuits.

  • Winter Park Visitor Center: This vibrant centre is your gateway to adventure, offering a wealth of information on outdoor activities and family-friendly experiences. Engage with knowledgeable staff and discover local attractions, trails, and events to enhance your stay.
  • Cozens Ranch House Museum: Located 621m from Winter Park, this charming historic house invites you to explore the rich culture and history of the area. Walk through its well-preserved rooms and gardens, showcasing the lives of early settlers.
  • Moffat Tunnel West Portal: Situated within Winter Park, this historic rail site offers a fascinating glimpse into the engineering marvel of the Moffat Tunnel. Experience the cultural significance of this iconic railway, surrounded by stunning mountainous scenery.

Things to do recommended for couples

For a romantic getaway in Winter Park, indulge in skiing at the Winter Park Ski Resort, take an adventurous ride on the Gondola, and unwind together at the serene Ranch Creek Spa. These experiences offer the perfect blend of excitement and relaxation for couples.

Things to do recommended for families

Families will have a delightful time at Trestle Bike Park and the Grand Park Community Recreation Centre, both offering wellness vibes. A short drive away, the Carousel of Happiness promises outdoor fun for all ages, making Winter Park a fantastic family-friendly destination.

Things to do recommended for groups

Explore the scenic Fraser River Trail for a delightful hike, tackle the thrilling Amaze'n Maze for an adventurous zipline experience, or enjoy a round of golf at Pole Creek Golf Club, just 5.0km from Winter Park, perfect for sports enthusiasts in your group.

Booking with Vrbo is simple

Looking to cut costs on your next holiday? Consider being flexible with your travel dates, as this can result in significant price differences. Moreover, opting for a longer stay frequently brings about excellent savings. To discover the ideal Vrbo accommodation that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Where to stay in and around Winter Park

Winter Park, Colorado, offers an enchanting blend of adventure and relaxation, making it an ideal destination for families and couples alike. With its stunning ski slopes, picturesque scenery, and numerous recreational activities, visitors can enjoy unforgettable excursions. Nearby towns also provide a charming atmosphere for romantic getaways and family vacations, ensuring a memorable experience for all. Whether you're seeking exhilarating sports or tranquil family time, Winter Park has something for everyone.

  • Fraser: Located a mere 1.2km from Winter Park, Fraser is a charming town that offers a wealth of adventure for outdoor enthusiasts. Renowned for its skiing and sports experiences, Fraser is a gateway to some of the best ski resorts in the region. The proximity to national parks and breathtaking lakes makes it an ideal base for exploration. Visitors can partake in various activities, from skiing on pristine slopes to enjoying the stunning natural scenery that surrounds the area. Fraser’s welcoming community and vibrant atmosphere ensure a memorable experience.
  • Rendezvous: Just 621m away from Winter Park, Rendezvous is a picturesque neighborhood that invites visitors to immerse themselves in the thrill of skiing and outdoor adventures. This area boasts easy access to ski fields and resorts, making it perfect for both seasoned skiers and beginners. With nearby national parks and serene lakes, you’ll find ample opportunities for exploration and relaxation. The charm of Rendezvous lies in its blend of adventure and tranquillity, making it a desirable spot for those looking to enjoy the beauty of Colorado’s landscapes.
  • Old Town Winter Park: Nestled around the area of Winter Park, Old Town Winter Park is a delightful neighbourhood that invites visitors to experience the heart of this mountain town. Known for its skiing opportunities and adventurous spirit, it provides easy access to world-class ski resorts and field activities. The surrounding national parks and tranquil lakes enhance the appeal, offering breathtaking views and activities for all seasons. Old Town Winter Park is the perfect destination for those seeking a blend of excitement and relaxation in a stunning mountain setting.

Best time to go to Winter Park

If you're planning a trip to Winter Park, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from December to February, while off-peak times, like May to June and August tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January14.2°F (-9.9°C)No Rain (Dry)Mostly SunnyModerately HighAverage
February15.6°F (-9.1°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
March23.4°F (-4.8°C)Light RainMostly SunnyAverageSlightly High
April29.8°F (-1.2°C)Light RainMostly SunnyAverageSlightly Low
May39.4°F (4.1°C)Light RainMostly SunnyModerately LowSlightly Low
June52.3°F (11.3°C)No Rain (Dry)SunnyModerately LowAverage
July57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
August56.3°F (13.5°C)No Rain (Dry)SunnyModerately LowAverage
September50.2°F (10.1°C)No Rain (Dry)SunnyAverageAverage
October35.6°F (2.0°C)No Rain (Dry)SunnyAverageSlightly Low
November23.4°F (-4.8°C)No Rain (Dry)Mostly SunnyAverageAverage
December14.4°F (-9.8°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High

What do I need to keep in mind when booking a vacation in 'Winter Park

When planning your trip—be it with friends, family, pets, or if you're considering an extended stay—it's important to filter your options according to your specific needs. Here are some helpful tips for booking on Vrbo.

  • Traveling to Winter Park with a group: Think about how many bedrooms you require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all of these options, and much more, on Vrbo.
  • Traveling to Winter Park with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, alongside suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winter Park: For many, a family holiday wouldn’t feel complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels at ease.
  • Planning for a long term stay visiting Winter Park: If you're in search of holiday rentals offering discounts for month-long stays, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider additional amenities such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient space for you to plan new journeys, refine your existing arrangements, or keep track of your bookings. The properties you've saved or reserved are thoughtfully organised into categories such as Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The cosy city of Winter Park awaits you

Enjoy the live music and other features of Winter Park. Renowned for its skiing, mountain views and snowboarding, this city welcomes all visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Winter Park

Do you want to find attractions to see during your stay? Travellers enjoy Winter Park for its skiing, snowboarding and hiking. Venture out of your cosy holiday rental and experience everything that makes Winter Park a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Winter Park Ski Resort (3.7 mi / 5.9 km)
  • Keystone Ski Resort (25.5 mi / 41.1 km)
  • Trestle Bike Park (2.5 mi / 4.1 km)
  • Pole Creek Golf Club (7.7 mi / 12.3 km)
  • Ski Granby Ranch (10.3 mi / 16.6 km)
  • Eldora Mountain Resort (10.7 mi / 17.3 km)

Exploring the mountains and other natural features in Winter Park

Whether you're an adventurous traveller or just want to appreciate the scenery, Winter Park is a great place to spend some time outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Rocky Mountain National Park (29.7 mi / 47.9 km)
  • The Fraser River Trail (2.6 mi / 4.1 km)
  • Saint Mary's Glacier (9.1 mi / 14.7 km)
  • Georgetown Lake (14.1 mi / 22.7 km)
  • Torreys Peak (16 mi / 25.8 km)
  • Lake Granby (16.4 mi / 26.3 km)

Seasonal weather averages in Winter Park

Winter Park is well known for its skiing. If you're interested in winter sports, you might consider visiting in January, February, March or April, when snowfall averages 67 cm and temperatures average -8°C.

Travelling to and around Winter Park

The nearest airport is in Broomfield, CO (BJC-Rocky Mountain Metropolitan), located 35.7 mi (57.4 km) from the city centre.

If you'd prefer to travel by train, the main station is Winter Park Ski Resort Amtrak Station.

Frequently asked questions

What is the best area to stay in Winter Park when booking a holiday rental?
Old Town Winter Park is one of the more sought-after locations for a holiday property in Winter Park. Spend your stay here to savour the comfort and privacy that comes with having the entire place to yourself.
What is the most popular type of holiday rental accommodation in Winter Park?
The most desirable types of holiday rentals in Winter Park are condos. Prefer something different? Vrbo has numerous options to match our guests' unique requirements, so you'll see holiday homes in loads of sizes and shapes. The perfect fit is waiting for you --- book yours today.
How much does it cost to rent a holiday rental in Winter Park?
Different factors affect the price of a holiday rental in Winter Park, such as the time of year, length of stay and property type. However, all our holiday homes have something in common --- exceptional value. Just add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Winter Park?
When you travel and the style and size of the property will determine the cost of your beachside escape. Put in your Winter Park travel dates to see your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use the filters to pick the amenities and features you want in your holiday home.
Are there pet-friendly holiday rentals in Winter Park?
Pack a travel bag and a bone for the pup in your life because Winter Park has 598 stays that open their doors to pets. Let your four-legged friend get in on the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Winter Park?
Tick the "pool" box in our handy filter tool and select from 255 houses with private pools in Winter Park on Vrbo. Ball games, gentle soak or noodle joust? Free time is up to you when your Vrbo holiday home comes with a swimming pool.
What are popular rental amenities in Winter Park?
Some of the most popular rental amenities guests are looking for in Winter Park are tennis, a chef and a lake view. Whether you're travelling with family, buddies or even pets, Vrbo holiday properties feature the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group holiday rentals in Winter Park?
Winter Park has 101 holiday properties that can fit 10 or more people. These properties come with the space and privacy you need to share good times with your nearest and dearest.
Are there holiday rentals in Winter Park that welcome kids?
With 598 family-friendly holiday rentals available in Winter Park, now is a fantastic time to introduce your children to the pleasures of travel. Simply check our "Properties good for families" filter box to view stays packed with amenities perfect for families on the move, such as multiple bedrooms, yards, bunk beds and entertainment areas.
What are the top attractions for families in Winter Park?
There are plenty of amazing things to see and do with the family in Winter Park, including:

  • Amazen Maze Winter Park
  • Moffat Tunnel West Portal
  • Trestle Bike Park

Are there one-bedroom holiday rentals in Winter Park?
You'll find 106 one-bedroom properties in Winter Park to choose from. A one-bedroom holiday home is a wonderful choice if it's just you and your partner or if you're holidaying alone. Toss in more convenience, space and privacy compared to a hotel, and you're bound to have a memorable trip.
Can I find two-bedroom holiday rentals in Winter Park?
Gather your nearest and dearest and enjoy peace, privacy and comfort in one of the 221 two-bedroom holiday properties Winter Park has to offer.
Are there holiday rentals with WiFi in Winter Park?
Whether you want to keep up with the headlines, reply to emails or surf your social networks, there are 157 holiday homes with WiFi in Winter Park. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Winter Park?
You can pick from 27 Vrbo holiday homes with air conditioning in Winter Park giving you that gentle, cool breeze and extra element of comfort. Enter your chosen travel dates and then use our filter tool to search for stays with air conditioning.
How old do you have to be to rent a holiday rental in Winter Park?
We recommend checking with the Winter Park holiday rental you'd like on Vrbo as the minimum age differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Winter Park for?
How long you can rent a holiday rental in Winter Park is down to the property. Simply enter your chosen travel dates to look at a list of options offering extended stays. With loads of amenities like laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere just right to call your home away from home in Winter Park.

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