Winter Park holiday lettings

We found 546 holiday rentals — enter your dates for availability

Discover a selection of 12 homes, 14 cabins and other holiday rentals in Winter Park that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, including parking and a TV. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Winter Park

Showing deals for:6 Feb - 13 Feb
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Why visit Winter Park

  • Scenic skiing: Winter Park is renowned for its excellent skiing facilities, perfect for both beginners and seasoned skiers.
  • Adventure sports: Enjoy a range of outdoor activities, including hiking, mountain biking, and water sports at the nearby marinas.
  • Family-friendly atmosphere: The charming neighbourhood offers a variety of excursions suitable for families looking to bond and create memories.
  • Charming accommodations: Choose from cosy cabins, stylish apartments, or private holiday homes tailored to your needs.
  • Serene surroundings: Experience the welcoming locals and peaceful ambience, ideal for relaxation and rejuvenation.

Popular types of accommodation around Winter Park

Planning a getaway to Winter Park? The next step is selecting your ideal accommodation. Discover the most sought-after options, including private holiday homes, cosy cabins, and stylish apartments. Whether you're seeking festive holiday rentals or a tranquil retreat, Winter Park has a range of options to suit every traveller. Explore our collection of holiday rentals and find the perfect base for your adventure.

  • Houses: A top choice among visitors to Winter Park, these homes offer spacious and comfortable stays, ideal for families and groups.
  • Cabins: Perfect for those seeking a rustic experience, cabins provide a cosy retreat amidst nature's beauty.
  • Apartments: A convenient option for couples or small families, apartments offer the comforts of home in a compact setting.
  • Condos: These stylish accommodations combine modern amenities with a prime location, perfect for a relaxed getaway.
  • Chalets: Offering a charming alpine vibe, chalets are a delightful choice for a unique and memorable stay.**

Top attractions near Winter Park

Winter Park in Big Bear Lake, California, is an ideal destination for skiing and adventure sports enthusiasts. Visitors can explore a variety of attractions, including marinas, visitor centres, and stunning mountains, perfect for outdoor experiences. Whether you're seeking a relaxing escape or thrilling adventures, Winter Park offers ample opportunities to enjoy the great outdoors and local activities. Be sure to consider options like Winter Park Explore and Winter Park Escapes for a memorable holiday.

  • Bear Mountain: A majestic mountain located 1.9km from Winter Park, Bear Mountain is a haven for outdoor enthusiasts. With stunning scenery, it offers a variety of adventure activities, including hiking and skiing, making it ideal for thrill-seekers and nature lovers alike.
  • Big Bear Visitor Center: Situated 1.2km from Winter Park, the Big Bear Visitor Center is the perfect starting point for families. It provides valuable information about local attractions and outdoor adventures, ensuring a memorable experience for all.
  • Big Bear Marina: Located 1.2km away, Big Bear Marina is an adventure hotspot. With its beach vibes, it offers boating, fishing, and water sports, promising a fun-filled day by the lake.

Things to do recommended for couples

For a romantic getaway in Winter Park, indulge in skiing at Snow Summit, a mere 373m away. Take an adventurous ride on the Chair 4 or East-Mountain Xpress Lift, both located just 311m away, offering thrilling views and unforgettable memories together.

Things to do recommended for families

During your family holiday in Winter Park, enjoy the Alpine Slide at Magic Mountain for thrilling rides, relax at Boulder Bay Park, and have fun at the Bowling Barn for arcade adventures, all within a short drive of your accommodation.

Things to do recommended for groups

Explore the vibrant Village, a mere 1.2km from Winter Park, for shopping and dining. Alternatively, indulge in a round of golf at Bear Mountain Golf Course, also 1.2km away, or visit the Interlaken Shopping Centre, only 497m away, for family-friendly entertainment.

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

If you’re travelling with a group, as a family, with your pets, or seeking extended stays, be sure to narrow your search according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Winter Park with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winter Park with young kids: Traveling with young children can present its challenges. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities, such as a private swimming pool. Additionally, it's wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Winter Park: For many, a family holiday isn't truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winter Park: If you're seeking holiday rentals with offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include additional preferences in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay near Winter Park

Winter Park, California, offers an exhilarating blend of adventure and relaxation, making it an ideal destination for a ski holiday or sports getaway. Nestled amidst stunning scenery, this charming neighbourhood is perfect for family-friendly excursions. Just a stone's throw away, nearby areas boast friendly locals and serene atmospheres, ensuring a memorable vacation experience. Whether you're seeking thrilling activities or a peaceful retreat, Winter Park and its surroundings present a perfect spot for a delightful getaway.

  • Big Bear Lake: Nestled just 1.2km from Winter Park, Big Bear Lake is a charming city renowned for its adventurous spirit and stunning outdoor experiences. The picturesque lake serves as a focal point for visitors, offering a plethora of activities such as skiing, boating, and kayaking. In the winter months, ski resorts and ski fields attract winter sports enthusiasts eager to hit the slopes. With its scenic beaches and vibrant theme park, Big Bear Lake is ideal for families and outdoor lovers alike, providing ample opportunities for relaxation and recreation.
  • Big Bear City: Located 3.1km from Winter Park, Big Bear City is a delightful destination for those seeking adventure and natural beauty. This city is closely associated with outdoor activities, particularly skiing, given its proximity to ski resorts and ski fields. Visitors can also explore the stunning national state park nearby, perfect for hiking and nature walks. With a charming atmosphere and local attractions like the lake and theme park, Big Bear City offers a perfect blend of excitement and tranquillity for all types of travellers.
  • Summit Estates: Just 62m from Winter Park, Summit Estates is a quaint neighbourhood that embodies the essence of mountain living. Known for its skiing and sports activities, this area provides quick access to nearby ski resorts and fields, making it a popular choice for winter sports enthusiasts. Surrounded by breathtaking mountains and the serene lake, visitors can enjoy a variety of outdoor activities year-round, including hiking and beach outings. Summit Estates is the perfect base for those looking to immerse themselves in the natural beauty of the region.

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 in July and December to January, while off-peak times, like May and September to October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January42.6°F (5.9°C)No Rain (Dry)SunnyModerately HighSlightly High
February43.0°F (6.1°C)No Rain (Dry)SunnyAverageSlightly High
March46.8°F (8.2°C)No Rain (Dry)SunnyAverageAverage
April53.2°F (11.8°C)No Rain (Dry)SunnyAverageSlightly Low
May59.0°F (15.0°C)No Rain (Dry)SunnyModerately LowSlightly Low
June68.7°F (20.4°C)No Rain (Dry)SunnyAverageAverage
July74.3°F (23.5°C)No Rain (Dry)SunnyModerately HighAverage
August73.6°F (23.1°C)No Rain (Dry)SunnyAverageAverage
September68.7°F (20.4°C)No Rain (Dry)SunnyModerately LowAverage
October58.6°F (14.8°C)No Rain (Dry)SunnyModerately LowSlightly Low
November49.1°F (9.5°C)No Rain (Dry)SunnyAverageAverage
December42.1°F (5.6°C)Light RainSunnyModerately HighSlightly High

Booking with Vrbo is a breeze

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

Vrbo Trips: Planning made easy

Vrbo’s innovative Trip Board offers you a dedicated area to plan new journeys, pick up where you paused, or review and arrange your travel plans. You can easily access properties you’ve previously saved and booked, now categorised under Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Winter Park?
Prices for holiday rentals in Winter Park vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winter Park to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winter Park holiday house rentals?
You can find great discounts on house rentals in Winter Park on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Winter Park holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winter Park with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Winter Park?
A long-stay holiday rental in Winter Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Winter Park for a holiday rental?
July is the most popular time to visit Winter Park, drawing in families and adventure seekers eager to embrace the stunning outdoor activities that the area has to offer. During the peak season, which runs from June through August, visitors can take full advantage of warm temperatures, typically ranging from 20 to 30 degrees Celsius, making it ideal for hiking, mountain biking, and exploring the picturesque landscapes.

In July, the town comes alive with a vibrant atmosphere, with plenty of events and activities to enjoy. The clear skies and lush surroundings create great conditions for outdoor adventures, whether you're trekking through the scenic trails or enjoying the local festivals that celebrate the summer spirit.

If you are looking for a more budget-friendly option, consider planning your trip in February. During this month, Winter Park offers a quieter experience with beautiful winter scenery and the opportunity to enjoy activities like skiing and snowboarding. The chill in the air, with temperatures often between -5 and 5 degrees Celsius, makes it a delightful time for those who appreciate the magic of winter sports, all while avoiding the larger crowds of the high season.
How early should I book a Winter Park holiday rental?
Book your Winter Park holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Winter Park home rental booking on Vrbo?
To find Winter Park holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winter Park holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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