Winter Park holiday rentals

We found 575 holiday rentals — enter your dates for availability
Discover a selection of 11 homes, 13 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:4 Dec - 11 Dec

Fully equipped cabin kitchen with ample cabinetry, stove, fridge, microwave, and coffee maker—perfect for cooking meals, morning coffee, and feeling right at home on your stay.
This expansive open-concept space features high vaulted ceilings, a cozy stone fireplace, and a pool table for entertainment. With a wooden bar and dining setup, it's the ultimate spot for group fun and relaxation.
Fun-filled game room with a pool table—perfect for family fun, friendly competition, and unforgettable entertainment during your stay.
Private outdoor hot tub, a BBQ, surrounded by tall pines, perfect for relaxing under the trees after a day of adventure—enjoy peaceful forest views, fresh air, and a truly rejuvenating stay.
Wonderful
(9 reviews)

"Moose Creek Chalet" | Walk to Snow Summit! Hot Tub, Pool Table & 4-Car Parking

Big Bear Lake

7% off
AU$4,594
for 7 nights, 1 cabin
AU$656 per night
includes taxes & fees
"Moose Creek Chalet" | Walk to Snow Summit! Hot Tub, Pool Table & 4-Car Parking
Outdoor dining
Dining
Interior
Private kitchen
Exceptional
(22 reviews)

Modern Lux Chalet • Spa • Game Room • EV Charger

Big Bear Lake

8% off
AU$13,205
for 7 nights, 1 home
AU$1,886 per night
includes taxes & fees
Modern Lux Chalet • Spa • Game Room • EV Charger
Dining
Private kitchen
Living area
Exterior
Exceptional
(5 reviews)

8 Bedroom, 12 Beds - Gameroom, Basketball & Golf

Big Bear Lake

8% off
AU$13,309
for 7 nights, 1 home
AU$1,901 per night
includes taxes & fees
8 Bedroom, 12 Beds - Gameroom, Basketball & Golf
Perfect for couples, families, or anyone seeking a comfortable and stylish home
Exterior
Dining
Barstools are perfect for breakfast.
Exceptional
(22 reviews)

AC + <5mins to Village/Shops/BikePark/Zoo + FirePit

Big Bear Lake

7% off
AU$3,356
for 7 nights, 1 cottage
AU$479 per night
includes taxes & fees
AC + <5mins to Village/Shops/BikePark/Zoo + FirePit
Third Floor Bedroom #4 - opens to upper deck
Deck Patio bar
Kitchen
Backyard
Exceptional
(67 reviews)

Perfect Family Getaway, One Light to Snow Summit, Bear Mountain and Shopping

Big Bear Lake

21% off
AU$4,386
for 7 nights, 1 cabin
AU$627 per night
includes taxes & fees
Perfect Family Getaway, One Light to Snow Summit, Bear Mountain and Shopping
Fully equipped cabin kitchen with ample cabinetry, stove, fridge, microwave, and coffee maker—perfect for cooking meals, morning coffee, and feeling right at home on your stay.
Welcoming cabin entry surrounded by towering pine trees, offering fresh mountain air and a peaceful forest setting—the perfect first impression for your Big Bear Lake getaway.
Peaceful cabin bedroom with plush bedding, and beautiful views—ideal for restful nights, cozy mornings, and a relaxing mountain escape.
Cozy mountain living room with a stone fireplace, comfy seating, and smart TV—perfect for relaxing evenings, movie nights, and warm cabin vibes after outdoor adventures.
Exceptional
(50 reviews)

Retreat To Fox Farm Central Log Cabin Chalet at Big Bear

Big Bear Lake

7% off
AU$3,599
for 7 nights, 1 cabin
AU$514 per night
includes taxes & fees
Retreat To Fox Farm Central Log Cabin Chalet at Big Bear

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

When is the best time to visit Winter Park for a holiday rental?
The best time to visit Winter Park for a holiday rental is during the peak season from June to August, when the area comes alive with outdoor enthusiasts eager to explore the stunning Rocky Mountain landscapes. This is a prime time for hiking, mountain biking, and enjoying various outdoor festivals that showcase the vibrant local culture.July stands out as the most popular month, offering warm weather and a lively option filled with fellow travellers. With temperatures typically ranging from 15 to 25 degrees Celsius, it's great for indulging in activities, whether it's a scenic hike through the alpine meadows or a leisurely day at the nearby lakes.For those looking for a more budget-friendly option, February is an excellent choice. Although this is considered the low season, it presents a unique opportunity for winter sports enthusiasts. The snow-covered slopes offer excellent skiing and snowboarding conditions, and the serene surroundings create a peaceful retreat for those who appreciate a quieter experience.Ultimately, your choice of when to visit Winter Park will depend on whether you prefer the bustling summer months filled with outdoor adventures or the tranquil beauty of winter.
What are the top attractions in Winter Park, California, United States of America?
In Winter Park, California, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The Winter Park Resort is a major draw, offering year-round recreational opportunities, including skiing and snowboarding in the winter and mountain biking or hiking during the warmer months. The resort features a range of trails suitable for all skill levels, as well as scenic chairlift rides that provide stunning views of the surrounding mountains.For those interested in the local wildlife and stunning landscapes, the nearby Arapaho National Forest is great for hiking, camping, and exploring nature. The forest is home to numerous trails that lead through beautiful alpine scenery and provide opportunities for spotting wildlife.The charming downtown area of Winter Park offers a selection of shops, restaurants, and local events, making it a great place to unwind after a day of outdoor adventures. Nearby, the Fraser River Trail provides a scenic route for walking or biking, showcasing the area's natural beauty.
Are all fees included in the Winter Park holiday homes prices shown on Stayz?
Stayz 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.
Are there any Winter Park holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Winter Park holiday homes?
You can find great discounts on holiday homes in Winter Park on Stayz, 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.
Can I change or cancel my Winter Park holiday home booking on Stayz?
To find Winter Park holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winter Park?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winter Park holiday home?
Book your Winter Park holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winter Park?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winter Park to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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