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Old Town Winter Park vacation rentals

We found 587 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:May 15 - May 22

Image gallery for Luxury 5br 4.5 Bath, 2 Primary Bedrooms! Across from Ski Resort. License 005650

Winter View
10 out of 10, Exceptional, (104 reviews)
Exceptional
(104 reviews)

Luxury 5br 4.5 Bath, 2 Primary Bedrooms! Across from Ski Resort. License 005650

Winter Park

5% off
Price is $543
$3,803 for 7 nights
All fees included
Luxury 5br 4.5 Bath, 2 Primary Bedrooms! Across from Ski Resort. License 005650

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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, condos and vacation houses are the most popular types of vacation rentals, with about 31 condos and 30 vacation houses available throughout the area. These properties are typically located close to outdoor activities, allowing easy access to skiing and hiking trails. Most condos feature modern amenities such as fully equipped kitchens, cozy living areas, and often include access to hot tubs or fitness facilities. The vacation houses tend to offer more space, with multiple bedrooms, private yards, and outdoor seating areas, great for families or larger groups looking to enjoy the scenic mountain surroundings.
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, superb for preparing meals after a day on the slopes. Many properties feature cozy fireplaces, adding warmth and ambiance during colder months. Outdoor spaces such as decks or patios and balconies are common, providing guests with a chance to enjoy the fresh mountain air and scenic views. Additionally, most rentals are equipped with coffee and tea makers, allowing travelers to enjoy a warm beverage at their convenience.
Can I find family house rentals in Old Town Winter Park?
In Old Town Winter Park, there are some available family-friendly vacation rentals, with around 52 options to choose from. This charming area is superb for families looking to enjoy a mountain getaway, offering easy access to outdoor activities and local attractions. Many of these homes feature spacious living areas, fully equipped kitchens to prepare family meals, and cozy fireplaces for those chilly evenings.

Visitors can also find properties with amenities such as game rooms, hot tubs, and outdoor patios where kids can play and families can relax after a day of adventure. The proximity to Winter Park Resort makes it convenient for skiing and snowboarding in the winter, while summer activities like hiking and mountain biking are just a stone's throw away.

Additionally, the nearby town offers dining options and shops, enriching the overall experience.
Can I rent a vacation home with a pool or hot tub in Old Town Winter Park?
In Old Town Winter Park, travelers have several vacation home options that feature pools and an impressive selection of around 53 properties with hot tubs. This charming mountain town, known for its beautiful alpine scenery and proximity to skiing, offers a variety of rental choices in neighborhoods close to the slopes and downtown area.

Rentals in this region typically boast amenities such as private hot tubs for relaxation after a day of outdoor activities, and some properties may include access to shared or private pools, great for enjoying the summer months. Expect spacious living areas, fully equipped kitchens, and comfortable bedrooms, making these homes ideal 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.
Can I book pet-friendly vacation rentals in Old Town Winter Park?
Yes, you can book pet-friendly vacation rentals in Old Town Winter Park, with around 12 options available for travelers. Many of these rentals come equipped with amenities such as fully equipped kitchens, cozy living spaces, and some even feature outdoor spaces great for enjoying the mountain scenery.

The Old Town area is conveniently located near various outdoor activities, including hiking and biking trails, making it an excellent choice for those traveling with pets. Additionally, the nearby Winter Park Resort offers opportunities for skiing and snowboarding during the winter months.
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 month to visit Old Town Winter Park, as it falls within the peak season running from December to February. This time of year attracts winter sports enthusiasts eager to take advantage of the excellent skiing and snowboarding conditions at Winter Park Resort. With abundant snowfall and well-groomed slopes, visitors can experience thrilling outdoor activities amidst stunning mountain scenery.

During January, temperatures typically range from the low 20s to mid-30s Fahrenheit, providing a crisp, invigorating atmosphere for both skiing and cozy après-ski activities. Many vacation rentals offer easy access to the slopes, ensuring convenience for travelers looking to maximize their time on the mountain. Additionally, the charming town offers a variety of dining and entertainment options, making it an ideal destination for a winter getaway.

For those seeking a more budget-friendly experience, consider planning your visit in May, during the low season. This month brings milder temperatures and fewer crowds, allowing for a relaxed exploration of the beautiful hiking trails and scenic views that Winter Park has to offer. Plus, the lush greenery and blooming wildflowers create a picturesque backdrop for outdoor adventures.

Ultimately, the best time to visit Old Town Winter Park hinges on your preferences—whether you're drawn to the lively option of winter sports in January or the serene beauty of spring in May.
Are there any remote work vacation rentals in Old Town Winter Park?
In Old Town Winter Park, there are numerous options for remote work vacation rentals, with about 68 available. This charming area, known for its access to both outdoor activities and a cozy mountain town atmosphere, offers accommodations that cater specifically to those needing to work remotely. Many of these rentals provide amenities like high-speed internet, dedicated office spaces, and Wi-Fi, ensuring a productive environment.

Travelers can expect comfortable living areas equipped with desks and ample lighting, allowing for an efficient workspace. Many properties also feature cozy common areas where one can unwind after a day of work, as well as fully equipped kitchens for preparing meals. The proximity to local attractions, such as the Winter Park Resort and scenic hiking trails, allows for a great blend of 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, Colorado, United States of America?
In Old Town Winter Park, visitors can enjoy a cozy mountain atmosphere with various attractions. The Winter Park Resort is a major highlight, offering skiing and snowboarding in the winter, along with mountain biking and hiking trails in the warmer months. Nearby, the charming Historic Old Town area features shops, restaurants, and art galleries, providing a delightful walking experience.

The Fraser River Trail is superb for those looking to explore the natural beauty of the area, offering scenic views and opportunities for biking and walking. Additionally, the proximity to the Winter Park Village enhances the experience with its lively events and entertainment options throughout the year.
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.

Frequently asked questions

Are there vacation rentals in Old Town Winter Park?
Yes, we offer vacation rentals near well known points of interest in Old Town Winter Park, or you can choose a more secluded option if you want a relaxing place to stay.
How many vacation rentals will I find in Old Town Winter Park?
Expedia has 32 vacation rentals for your stay in Old Town Winter Park.
What can I see and do in Old Town Winter Park?
While exploring the area, visit family-friendly sights like Amaze'n Maze Winter Park, or get outside and enjoy nature at The Fraser River Trail. Winter Park Ski Resort and Trestle Bike Park are a couple of places you'll find in the larger area.
What's a vacation rental in Old Town Winter Park like?
Vacation rentals are privately owned properties you can stay in for a long or short time in Old Town Winter Park. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips.

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