Photo by Kayla Templin

Old Town Winter Park vacation rentals

We found 591 vacation rentals — enter your dates for availability

Select from 32 houses, 35 condos, and other vacation rentals to find the perfect place for your stay in Old Town Winter Park. Vacation rentals offer the amenities you expect for you and your friends, family, or even pets, such as WiFi and a hot tub. What you'll find is a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Old Town Winter Park

Showing deals for:Apr 17 - Apr 24

Image gallery for Updated Condo at Winter Park and Trestle Bike Park

Living area
9.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)

Updated Condo at Winter Park and Trestle Bike Park

Winter Park

8% off
Price is $216
$1,515 for 7 nights
All fees included
Updated Condo at Winter Park and Trestle Bike Park

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Old Town Winter Park

Why visit Old Town Winter Park

  • Winter Sports Paradise: Enjoy thrilling skiing and snowboarding at Winter Park Resort, a premier destination for winter sports enthusiasts.
  • Scenic Outdoor Attractions: Explore beautiful lakes, breathtaking glaciers, and inviting trails perfect for hiking and sightseeing.
  • Charming Local Shops: Discover unique treasures in local boutiques and shops, showcasing the area’s distinct character.
  • Rich Cultural Experience: Immerse yourself in the local culture and history, making for a memorable visit.
  • Diverse Accommodation Options: Choose from cozy condos, rustic cabins, or vintage hotels for a comfortable stay.

Popular types of accommodation around Old Town Winter Park

If you're planning a getaway to Old Town Winter Park, selecting the perfect vacation rental is essential. Popular choices include cozy condos, charming houses, and rustic cabins. Enjoy the convenience of free parking and the unique charm of a vintage hotel, all while keeping in mind that some rentals may offer limited amenities. Start exploring your options today for an unforgettable stay in this picturesque destination.

  • Condos: The top choice for vacation rentals in Old Town Winter Park, offering modern amenities and convenient locations.
  • Houses: A favored option for larger groups or families, providing a home-like atmosphere.
  • Cabins: A delightful retreat for nature lovers, these cozy accommodations blend rustic charm with comfort.
  • Apartments: Ideal for couples or solo travelers, these spaces offer flexibility and easy access to local attractions.
  • Chalets: A picturesque option that combines traditional style with comfort, perfect for ski enthusiasts.**

Top attractions near Old Town Winter Park

Old Town Winter Park is perfect for ski and adventure enthusiasts, offering a blend of scenic lakes, historic houses, and breathtaking glaciers. Travelers can enjoy a variety of winter activities at the Winter Park Resort, explore outdoor attractions near the Winter Park Visitor Center, and immerse themselves in the local culture. Whether you're seeking thrilling sports or serene landscapes, Old Town Winter Park has something for everyone seeking an unforgettable experience.

  • Winter Park Visitor Center: Located 2 miles from Old Town Winter Park, this center offers a wealth of information on local adventures, family-friendly activities, and outdoor experiences, making it a perfect starting point for your trip.
  • Saint Mary's Glacier: Situated 7 miles away, this stunning glacier is a visual feast, offering breathtaking scenery that attracts nature lovers and photographers alike.
  • Moffat Tunnel West Portal: Just 0.3 miles from Old Town, this historic railroad portal is rich in local culture and history, making it a fascinating spot for history enthusiasts.

Things to do recommended for couples

For a romantic getaway in Old Town Winter Park, take a scenic ride on the Gondola or Arrow Chair Lift, both offering thrilling views and adventure. Unwind together at Bella Vita for a rejuvenating body treatment, perfect for relaxation and connection.

Things to do recommended for families

Families visiting Old Town Winter Park can experience the thrill of Trestle Bike Park, just 0.3 miles away, enjoy the fun of the Alpine Slide, located 0.5 miles away, and relax at the Grand Park Community Recreation Center, 3 miles from Old Town, offering wellness activities for all ages.

Things to do recommended for groups

Explore the scenic Fraser River Trail, just 0.3 miles from Old Town Winter Park, for a memorable hike. For thrill-seekers, Amaze'n Maze Winter Park offers an exciting zipline ropes course 0.4 miles away. Don't miss a round of golf at Pole Creek Golf Club, located 10 miles from town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Old Town Winter Park with a group: Think about how many bedrooms you’ll require, along with features like a fully-equipped kitchen or outdoor areas for gatherings. Fortunately, you can easily filter for these options and more on Vrbo.
  • Traveling to Old Town Winter Park with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Old Town Winter Park: For many, a family vacation isn't truly satisfying unless their furry companion is along for the ride. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that all family members feel comfortable and at home.
  • Planning for a long term stay visiting Old Town Winter Park: If you're in search of vacation rentals that offer discounts 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 rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Old Town Winter Park

Old Town Winter Park offers a charming blend of adventure and relaxation, perfect for your next getaway. Explore local shops filled with unique treasures, enjoy family-friendly activities, and discover friendly trails that showcase the stunning scenery. With its rich history and welcoming atmosphere, this neighborhood is an ideal base for skiing and outdoor sports, making it a must-visit destination for travelers seeking both excitement and tranquility.

  • Winter Park: Winter Park is a captivating city known for its exceptional outdoor adventure and winter sports. Nestled in the heart of the Rockies, it offers easy access to world-class ski resorts and beautiful ski fields, attracting enthusiasts from far and wide. In addition to skiing, visitors can explore the nearby national and state parks, where breathtaking landscapes abound. Lake access provides opportunities for fishing, kayaking, and enjoying serene views. With vibrant local dining and shopping experiences, Winter Park is an ideal destination for those seeking both adrenaline and relaxation.
  • Fraser: Located just 5 miles from Old Town Winter Park, Fraser is a charming city that offers a similar allure of adventure and sports. Known for its fantastic ski resorts and access to extensive ski fields, Fraser is perfect for thrill-seekers. Outdoor enthusiasts will appreciate the proximity to stunning national and state parks, as well as lakes that offer a variety of recreational activities. The friendly atmosphere and local eateries provide a delightful taste of mountain culture, making Fraser a great spot to unwind after an adventurous day.
  • Hideaway Village South: Situated 2 miles from Old Town Winter Park, Hideaway Village South is a serene neighborhood ideal for travelers seeking a cozy retreat. This area boasts easy access to ski resorts and picturesque ski fields, appealing to winter sports lovers. With nearby lakes and parks, visitors can enjoy a range of outdoor activities, from hiking to picnicking. The quiet charm of Hideaway Village South allows for a peaceful getaway, while still being close to the vibrant offerings of Winter Park, making it a perfect base for your adventure.

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can really help, as prices often vary. Additionally, opting for a longer stay can lead to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your full booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new adventures, pick up right where you left off, or manage and organize your travel arrangements. You can easily access your previously saved and booked properties by checking the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Old Town Winter Park?
In Old Town Winter Park, vacation houses are the most popular type of rental, with about 28 available throughout the area. These properties are typically spacious, featuring multiple bedrooms, fully equipped kitchens, and cozy living areas—ideal for families or groups looking to enjoy the nearby ski slopes and outdoor activities. Additionally, there are around 22 condos available, which often come with amenities such as hot tubs, ski storage, and access to communal facilities. For those seeking a more rustic experience, several cabins and chalets provide a charming retreat with outdoor spaces for relaxation and stunning views of the surrounding mountains.
How much does it cost to rent a vacation home in Old Town Winter Park?
Prices for vacation rentals in Old Town 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 Old Town 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 Old Town Winter Park vacation house rentals?
You can find great discounts on house rentals in Old Town 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.
What are popular rental amenities in Old Town Winter Park?
In Old Town Winter Park, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals after a day of outdoor activities. Many rentals offer stunning mountain views, providing a picturesque backdrop for a relaxing stay. Guests can also enjoy outdoor patios for soaking in the fresh mountain air, while fireplaces add a cozy touch, superb for warming up in the evenings. Additionally, coffee and tea makers are commonly found in these rentals, ensuring that guests can enjoy a hot beverage at their convenience.
Are there any family house rentals in Old Town Winter Park?
In Old Town Winter Park, a variety of family-friendly house rentals are available, with around 45 options to choose from. This charming area is close to popular attractions like Winter Park Resort, where families can enjoy skiing and snowboarding in the winter months, as well as hiking and mountain biking during the warmer seasons.

The homes here often come equipped with spacious living areas, full kitchens for preparing meals together, and amenities such as cozy fireplaces and game rooms to keep everyone entertained. Many properties also feature outdoor spaces, great for children to play or for families to gather after a day of adventures.
Can I rent a vacation home with a pool or hot tub in Old Town Winter Park?
In Old Town Winter Park, there are plenty of vacation homes available for rent that feature either pools or hot tubs, with around 15 options for properties with pools and 45 options with hot tubs. This picturesque mountain town is known for its proximity to skiing and outdoor activities, making it an ideal destination for travelers seeking both relaxation and adventure.

Properties in this area often include desirable amenities such as spacious living areas, fully equipped kitchens, and cozy fireplaces, superb for unwinding after a day on the slopes. Many rentals with hot tubs provide private outdoor spaces where guests can soak while enjoying stunning mountain views. Additionally, some homes may offer access to shared facilities, including heated pools and community hot tubs, enhancing the overall experience for families or groups.
Are there any Old Town Winter Park vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Old Town Winter Park with parking available—perfect for families or travelers 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.
Are there pet-friendly vacation rentals in Old Town Winter Park?
Yes, you can book pet-friendly vacation rentals in Old Town Winter Park, where there are about 12 options available for travelers. This charming area is known for its close proximity to both the Winter Park Resort and the beautiful surrounding mountains, making it an ideal spot for outdoor enthusiasts. Many of the vacation rentals here come equipped with amenities such as full kitchens, cozy fireplaces, and access to outdoor spaces like patios or balconies, great for relaxing after a day of adventure.

In Old Town Winter Park, you'll find easy access to various pet-friendly attractions, including the scenic trails of the Fraser River Trail, which is great for walking or hiking with your furry friends. Additionally, the local parks in the area often allow pets, providing ample opportunities for outdoor fun.
Can I find long-stay vacation rentals in Old Town Winter Park?
A long-stay vacation rental in Old Town Winter Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Old Town Winter Park for a vacation rental?
January is the most popular time to visit Old Town Winter Park, attracting winter sports enthusiasts eager to enjoy the excellent skiing and snowboarding conditions that the Rockies have to offer. This peak season, spanning from December to February, sees the resort bustling with activity as visitors take advantage of the pristine powder and well-groomed slopes.

With temperatures typically ranging from the low teens to mid-30s Fahrenheit, outdoor activities like skiing, snowshoeing, and cozying up by a fire after a day on the slopes are all highly enjoyable. The charming town also offers a variety of local shops and restaurants, providing the superb backdrop for a winter getaway.

For those looking to save on travel expenses, consider visiting in May. This month offers a unique charm as the area transitions into spring, with fewer crowds and the opportunity to explore hiking trails and scenic vistas with vibrant wildflowers. The mild weather, usually hovering in the 40s to 60s Fahrenheit, creates a comfortable setting for outdoor exploration and relaxation.

Ultimately, your ideal time to visit Old Town Winter Park will depend on whether you seek the excitement of winter sports during peak season or the peaceful beauty of the shoulder months when nature begins to bloom.
Are there any remote work vacation rentals in Old Town Winter Park?
In Old Town Winter Park, Colorado, there are numerous vacation rentals suitable for remote work, with around 56 options available. This charming area, known for its proximity to the Winter Park Resort and the stunning Rocky Mountain scenery, offers a variety of accommodations that cater to professionals needing a productive environment. Many of these rentals come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated desk spaces, and comfortable desk chairs, ensuring a conducive workspace while enjoying the beauty of the outdoors.

Travelers can expect amenities like fully equipped kitchens for convenient meal preparation, cozy living areas superb for relaxation after work hours, and often access to outdoor spaces or balconies with picturesque mountain views. The location also provides easy access to recreational activities such as skiing, hiking, and biking, making it an ideal spot for those who want to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Old Town Winter Park vacation rental?
Book your Old Town Winter Park vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Old Town Winter Park?
In Old Town Winter Park, visitors can take part in a charming mountain atmosphere with easy access to several attractions. The area is known for its proximity to the Winter Park Resort, which offers a variety of outdoor activities year-round, including skiing, snowboarding, and mountain biking. The historic downtown features quaint shops, local restaurants, and art galleries, making it a great spot for leisurely exploration.

Additionally, the nearby Fraser River Trail provides scenic views and opportunities for hiking and biking, while the Winter Park Village serves as a hub for entertainment and dining options. For those interested in nature, the surrounding mountains and parks, such as the Arapaho National Forest, offer breathtaking landscapes and numerous trails for outdoor enthusiasts.
Can I change or cancel my Old Town Winter Park home rental booking on Vrbo?
To find Old Town Winter Park vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Old Town Winter Park vacation 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

More Vacation Ideas