Winterwood vacation rentals

We found 92 vacation rentals — enter your dates for availability
Discover a selection of vacation rentals in Winterwood that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for hanging out with the people that matter most, including air conditioning and cable TV. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.

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Find out more about Winterwood

Why visit Winterwood

  • World-class skiing: Winterwood offers exceptional ski resorts perfect for both beginners and seasoned enthusiasts.
  • Stunning outdoor activities: Enjoy hiking, biking, and exploring the breathtaking scenery of Breckenridge.
  • Cultural experiences: Discover local arts centers and vibrant street life that showcase the area's rich heritage.
  • Family-friendly adventures: Winterwood caters to families with various activities suitable for all ages.
  • Comfortable accommodations: Choose from cozy condos, spacious homes, and charming cabins for a relaxing stay.

Popular types of accommodation around Winterwood

If you're wondering what type of accommodation awaits you in Winterwood, look no further. Our most popular options include cozy condos, spacious houses, and charming cabins. You'll find quality housing with a range of family rental listings and modern apartments, including the sought-after Brentwood Court Apartments. Enjoy the perfect getaway with all the comforts of home at Winterwood vacation rentals.

  • Condos: The top choice for vacation rentals in Winterwood, offering modern amenities and convenient access to local attractions.
  • Houses: A favorite for families and groups, providing spacious living areas and a home-like atmosphere.
  • Cabins: Ideal for those seeking a rustic experience, these charming retreats are nestled in nature.
  • Apartments: A practical option for solo travelers or couples, featuring essential comforts in a compact space.
  • Chalets: These picturesque accommodations combine luxury with mountain charm, perfect for a cozy getaway.**

Top attractions near Winterwood

Winterwood in Breckenridge, Colorado, is the perfect destination for ski and adventure enthusiasts, offering a variety of attractions like ski resorts, arts centers, and vibrant streets. Visitors can enjoy outdoor activities, cultural experiences, and family-friendly adventures in this picturesque setting. Don't miss the chance to explore the local points of interest that cater to diverse interests and make your vacation unforgettable.

  • Breckenridge Ski Resort: Experience the thrill of skiing or snowboarding at this renowned resort, boasting breathtaking mountain views and a variety of slopes for all skill levels. Enjoy a winter wonderland with outdoor adventures and cozy après-ski vibes.
  • Main Street: Stroll down this charming street filled with quaint shops, restaurants, and vibrant local culture. Experience the lively atmosphere and unique architecture that reflect the rich history of Breckenridge.
  • Breckenridge Riverwalk Center: Immerse yourself in the local arts scene at this cultural hub, hosting concerts, performances, and community events. Enjoy the scenic riverwalk and the beautiful mountain backdrop.

Things to do recommended for couples

For a romantic getaway in Breckenridge, indulge in skiing at Breckenridge Ski Resort, take a scenic ride on the BreckConnect Gondola, or enjoy the thrill of the Quicksilver SuperChair. These adventures, all just 2 miles from Winterwood, promise unforgettable moments together amidst stunning mountain views.

Things to do recommended for families

Families can explore the Breckenridge Recreation Center, just 1 mile from Winterwood, for wellness and relaxation. For some fun on ice, head to the Stephen C. West Ice Arena, located 3 miles away, or enjoy outdoor playtime at River Park and Playground, also 1 mile from Winterwood.

Things to do recommended for groups

Enjoy a day at the Breckenridge Golf Club, just 2 miles away, for some outdoor fun. Explore the charming shops and eateries on Main Street, located 5 miles from Winterwood. For adventure seekers, hike the scenic Peaks Trail, only 0.7 miles away.

*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 Winterwood

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 for you.

  • Traveling to Winterwood with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Fortunately, Vrbo allows you to filter for these essentials and much more.
  • Traveling to Winterwood with young kids: Traveling with little ones can be quite a challenge. It's important to prioritize their comfort and safety, along with 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 Winterwood: For many families, a vacation wouldn't feel complete without their furry companion. If that resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and bedding to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winterwood: 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Winterwood

Winterwood, Breckenridge offers a perfect blend of adventure and relaxation. Explore the stunning scenery while enjoying world-class skiing and outdoor sports. Nearby neighborhoods like Oakland Homes provide excellent shopping opportunities, and the great location makes it easy to access attractions. Don't miss the charming excursions along Swain Road and the beauty of the San Joaquin area. Experience the luxury and recreation that make Winterwood a fantastic vacation destination.

  • Breckenridge: Breckenridge is a charming mountain town renowned for its world-class skiing and vibrant outdoor adventure scene. Nestled within the Rockies, it's a hub for winter sports enthusiasts, boasting extensive ski resorts and picturesque ski fields. Beyond skiing, visitors can explore scenic hiking trails, enjoy vibrant local festivals, and indulge in a variety of dining options. Local landmarks include the stunning Breckenridge Ski Resort, the breathtaking national park, and beautiful lakes that offer year-round recreational opportunities. Breckenridge's rich mining history adds to its allure, making it a perfect blend of adventure and culture.
  • Historic District: Located just 2 miles from Winterwood, the Historic District of Breckenridge is a must-visit for those interested in the town's rich history. This charming neighborhood features well-preserved Victorian buildings and quaint streets that reflect Breckenridge's mining heritage. Visitors can enjoy a range of activities, including skiing at nearby resorts and exploring local shops and galleries. The proximity to the national state park and picturesque lakes makes it an ideal spot for outdoor activities. The Historic District’s unique character and vibrant atmosphere make it a delightful stop on your vacation.
  • Peak 8: Situated 2 miles from Winterwood, Peak 8 is a popular destination for thrill-seekers and nature lovers alike. Known for its stunning views and exceptional skiing opportunities, this neighborhood is home to a variety of ski fields and resorts. In the warmer months, visitors can hike scenic trails and take in the breathtaking natural landscapes. Nearby attractions include national parks and scenic streets that invite exploration. Peak 8 offers a perfect mix of adventure and relaxation, making it an essential stop for anyone looking to fully experience the beauty of Colorado.

Best time to go to Winterwood

If you're planning a trip to Winterwood, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from January to March, while off-peak times, like May and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January10.0°F (-12.2°C)No Rain (Dry)Mostly SunnyHighAverage
February11.3°F (-11.5°C)No Rain (Dry)Mostly CloudyHighModerately High
March18.9°F (-7.3°C)Light RainMostly SunnyHighModerately High
April25.2°F (-3.8°C)Light RainMostly SunnyAverageAverage
May34.9°F (1.6°C)Light RainMostly SunnyLowModerately Low
June46.9°F (8.3°C)Light RainSunnyAverageAverage
July52.9°F (11.6°C)Light RainMostly SunnyAverageAverage
August51.1°F (10.6°C)Light RainMostly SunnyAverageAverage
September45.3°F (7.4°C)Light RainMostly SunnyAverageModerately Low
October31.1°F (-0.5°C)No Rain (Dry)Mostly SunnyLowModerately Low
November18.9°F (-7.3°C)No Rain (Dry)Mostly SunnyLowAverage
December10.2°F (-12.1°C)No Rain (Dry)Mostly SunnyAverageModerately High

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, opting for a longer stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for planning your next adventures. You can easily create new trips, continue from where you last left off, or view and manage your existing plans. Your saved or booked properties will be neatly organized under categories like Potential, Upcoming, or Current Trips. To start exploring Trip Boards, head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Winterwood?
In Winterwood, vacation houses are the most popular rental option, with about 46 available throughout the area. These houses typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or larger groups seeking comfort and convenience. Additionally, there are around 17 condos, which offer a more compact stay with similar amenities, including kitchen facilities and cozy living spaces.
How much does it cost to rent a vacation home in Winterwood?
Prices for vacation rentals in Winterwood 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 Winterwood 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 Winterwood vacation house rentals?
You can find great discounts on house rentals in Winterwood 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 Winterwood?
In Winterwood, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties also feature cozy fireplaces, superb for warming up after a day of outdoor activities. Decks or patios are common, providing outdoor space for relaxation and enjoying the mountain views. Additionally, rentals often include coffee and tea makers for a convenient morning brew, and onsite parking is typically available for guests traveling by car.
Can I find family house rentals in Winterwood?
In Winterwood, Colorado, there are numerous family-friendly rental options—about 67 homes available for travelers. This mountain area is great for families seeking outdoor adventures and cozy accommodations. Many properties feature spacious living rooms, fully equipped kitchens for preparing meals, and dedicated play areas that keep children entertained. You'll often find amenities like hot tubs, fireplaces, and even game rooms, adding to the comfort and enjoyment of your stay.

Nearby, families can explore the breathtaking Rocky Mountain landscape, which offers opportunities for hiking, biking, and winter sports, depending on the season. The scenic trails and parks provide ample space for picnics and outdoor fun, ensuring that all ages can enjoy the beauty of the surroundings.
Can I rent a vacation home with a pool or hot tub in Winterwood?
In Winterwood, Colorado, travelers have a great selection of vacation homes with pools and hot tubs, with approximately 20 rentals featuring pools and around 65 that include hot tubs. This scenic area offers a cozy mountain atmosphere, ideal for relaxation after a day of outdoor activities. Many of these properties come equipped with amenities such as spacious living areas, well-appointed kitchens for home-cooked meals, and outdoor spaces superb for gathering with family or friends.

The presence of hot tubs provides an excellent way to unwind while enjoying the stunning mountain views. Additionally, some rentals may feature barbecue areas and fire pits, enhancing the outdoor experience.
Are there any Winterwood vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winterwood 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 Winterwood?
In Winterwood, Colorado, there are several pet-friendly vacation rentals available, providing a welcoming environment for travelers with pets. Many of these properties feature amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam. Travelers can expect cozy accommodations that often include features like fireplaces and hot tubs, superb for relaxing after a day of exploring the beautiful Colorado landscape.

The area is known for its stunning mountain views and access to outdoor activities, making it an ideal destination for pet owners who enjoy hiking and nature walks. Nearby trails and parks are great for taking pets out for exercise and play.
Can I find long-stay vacation rentals in Winterwood?
A long-stay vacation rental in Winterwood 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 Winterwood for a vacation rental?
The best time to visit Winterwood for a vacation rental is during the festive peak season, which spans from November to January. This is when the town truly comes alive, offering a magical winter wonderland that attracts visitors eager to experience snow sports and cozy getaways. December, in particular, is a highlight, as families and adventure seekers flock to the area for skiing, snowboarding, and the enchanting holiday spirit.

During this time, temperatures in Winterwood typically range from the low teens to mid-30s Fahrenheit, providing a crisp, invigorating climate great for outdoor activities. The scenic landscapes blanketed in snow create an ideal backdrop for winter hikes, snowshoeing, and simply enjoying the beauty of the season.

For those looking to enjoy a quieter experience while still soaking in the charm of Winterwood, consider visiting in May. This month is outside the main tourist season and allows for a more relaxed atmosphere, with blooming wildflowers and mild temperatures making it great for hiking and exploring the natural beauty of the area.
Are there any remote work vacation rentals in Winterwood?
In Winterwood, Colorado, there are numerous remote work-friendly vacation rentals available, with around 71 options to choose from. This picturesque area is ideal for those looking to blend work and leisure in a serene mountain setting. Many of these rentals come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated office spaces, and comfortable desks, ensuring that travelers can stay productive while enjoying their surroundings.

Additionally, the scenic beauty of Winterwood offers opportunities for outdoor activities, such as hiking and skiing, making it a great destination for both work and play. The properties typically feature cozy accommodations, with some offering scenic views, outdoor spaces, and amenities like fully equipped kitchens, which are ideal for longer stays. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Winterwood vacation rental?
Book your Winterwood 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 Winterwood, Colorado, United States of America?
In Winterwood, Colorado, visitors can enjoy a variety of attractions that showcase the area's natural beauty and outdoor activities. The nearby Rocky Mountain National Park is a major draw, offering stunning mountain landscapes, hiking trails, and opportunities for wildlife viewing. This park is superb for those looking to explore the great outdoors, with options for both casual walks and more challenging hikes.

The charming downtown area features local shops and restaurants that provide a taste of the community, along with seasonal events and festivals that celebrate the town's culture. For those interested in winter sports, the area is close to ski resorts like Eldora Mountain Resort, which offers skiing, snowboarding, and snowshoeing in the winter months.
Can I change or cancel my Winterwood home rental booking on Vrbo?
To find Winterwood 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 Winterwood 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.

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