Winterwood holiday lettings

We found 90 holiday rentals — enter your dates for availability

Discover a selection of 9 homes and other holiday rentals in Winterwood that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for hanging out with the people that matter most, including Wi-Fi and parking. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Winterwood

Showing deals for:6 Feb - 13 Feb

Image gallery for Peak 7 Breckenridge Retreat, 4 BR, views & trails!

Bright living and great room
10 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Peak 7 Breckenridge Retreat, 4 BR, views & trails!

Breckenridge, CO

8% off
Price is £2,723
for 7 nights, 1 chalet
£389 per night
includes taxes & fees
Peak 7 Breckenridge Retreat, 4 BR, views & trails!

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

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    More space, more privacy, more amenities — more value

Why visit Winterwood

  • Exceptional skiing: Winterwood is a haven for ski enthusiasts, offering access to top-notch ski resorts with stunning slopes.
  • Outdoor adventures: Delight in a range of outdoor activities, from hiking and biking in summer to snowshoeing in winter.
  • Charming local culture: Immerse yourself in the vibrant community with quaint markets and family homes reflecting the local lifestyle.
  • Artistic experiences: Explore arts centres showcasing local talent and cultural events throughout the year.
  • Varied accommodation: Choose from cosy condos, inviting cabins, and private vacation homes for a comfortable stay.

Popular types of accommodation around Winterwood

Planning a getaway to Winterwood? You're in for a treat! Explore a range of popular accommodations, including cosy condos, houses, and charming cabins. Whether you're interested in Winterwood apartments or the inviting Winterwood Gardens, there's something for everyone. Don't forget to check out Winterwood Inc. and Winterwood Albany for additional options. Your ideal retreat awaits!

  • Condos: The top choice for holiday accommodation in Winterwood, offering modern amenities and easy access to local attractions.
  • Houses: A fantastic option for families or groups seeking spacious and comfortable living arrangements.
  • Cabins: A charming retreat amidst nature, perfect for those wanting a rustic experience in the mountains.
  • Apartments: A convenient choice for couples or solo travellers, providing a cosy base in the heart of Winterwood.
  • Chalets: Offering a unique alpine experience, these lodgings combine comfort with stunning mountain views.**

Top attractions near Winterwood

Winterwood in Breckenridge, Colorado, is perfect for a ski or adventure holiday, boasting attractions such as ski resorts, vibrant streets, and arts centres. Visitors can enjoy a range of experiences focusing on culture, outdoor activities, and family fun. With plenty of local points of interest to explore, be sure to check reviews of Winterwood to enhance your visit and discover all it has to offer.

  • Breckenridge Ski Resort: A premier ski destination, this resort offers thrilling slopes for all levels, complemented by breathtaking mountain views and a vibrant après-ski scene, perfect for adventure seekers.
  • Main Street: The heart of Breckenridge, this charming street is lined with quaint shops, delightful eateries, and lively bars, capturing the essence of a bustling mountain town with a friendly atmosphere.
  • Breckenridge Riverwalk Center: A cultural hub, this arts centre hosts various performances and events, surrounded by stunning scenery, making it a perfect spot to enjoy the local arts scene.

Things to do recommended for couples

For a romantic getaway in Winterwood, indulge in skiing at Breckenridge Ski Resort, just 1.2km away. Take a scenic ride on the BreckConnect Gondola for stunning views, or enjoy the thrill of the Beaver Run SuperChair ski lift. Perfect for couples seeking adventure together!

Things to do recommended for families

Your family will love the Breckenridge Recreation Center, just 621m from Winterwood, offering wellness and relaxation. For more adventure, visit the Stephen C. West Ice Arena, 1.9km away, for some ice skating fun. Don't miss Woodward at Copper, 2.5km away, for a thrilling experience!

Things to do recommended for groups

Groups visiting Winterwood can enjoy a round of golf at the nearby Breckenridge Golf Club, indulge in shopping along Main Street, or embark on an adventurous hike along the scenic Peaks Trail, all perfect for creating memorable experiences together.

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

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, be sure to refine your search according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winterwood with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Winterwood with young kids: Taking a trip with young children can pose certain challenges. It's essential to prioritise their comfort and safety, along with suitable amenities like private swimming pools. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winterwood: For many, a family holiday wouldn’t feel complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels completely at home.
  • Planning for a long term stay visiting Winterwood: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Winterwood

Winterwood, nestled in Breckenridge, Colorado, offers a delightful blend of adventure and tranquillity. Ideal for skiing enthusiasts and those seeking outdoor activities, this charming neighbourhood boasts stunning scenery and a welcoming community. Nearby, you'll find family homes and quaint markets, perfect for immersing yourself in local culture. Explore the surrounding areas for luxurious relaxation and exhilarating excursions, making your stay in Winterwood a memorable escape.

  • Breckenridge: Breckenridge is a charming town located a mere 1.2km from Winterwood, famed for its vibrant ski culture and adventurous spirit. As a popular destination for skiing enthusiasts, it boasts superb ski fields and resorts that attract visitors year-round. Beyond winter sports, Breckenridge offers a delightful blend of shops, restaurants, and local art galleries. Notable attractions include the breathtaking views of the nearby national parks and serene lakes, making it a fantastic base for outdoor adventures and a rich cultural experience.
  • Historic District: Nestled just 1.2km from Winterwood, the Historic District is a picturesque neighbourhood that showcases Breckenridge’s rich history and heritage. Visitors flock to this area for its charming architecture and vibrant community atmosphere. The Historic District provides easy access to ski fields and resorts, appealing to those looking for an exhilarating winter experience. Stroll down its inviting streets lined with quaint shops and eateries, and take in the stunning vistas of the nearby national parks and lakes, which add to the area's allure.
  • Peak 8: Peak 8, located 1.2km away from Winterwood, is a popular neighbourhood renowned for its stunning mountain views and exceptional skiing opportunities. This area is perfect for adventure seekers, offering access to top-notch ski resorts and fields. The breathtaking landscape surrounding Peak 8 features both national parks and serene lakes, inviting exploration and outdoor activities. After a day on the slopes, unwind at local eateries and take in the natural beauty that this neighbourhood has to offer, making it an ideal stop for any traveller.

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 a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can be advantageous, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, refine your travel arrangements, or manage your existing bookings. Your saved or reserved properties are thoughtfully categorised into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Winterwood?
In Winterwood, holiday houses are the most popular type of rental, with about 51 options available throughout the area. These spacious properties are ideal for families or groups, often featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios for enjoying the mountain views. The neighbourhoods surrounding Winterwood provide a tranquil setting, superb for those looking to relax after a day of outdoor activities.
Are there any beach house rentals in Winterwood?
In Winterwood, Colorado, beach house rentals are available, although the area is not typically associated with traditional beach holidays due to its mountainous terrain. However, visitors can find a selection of unique lodgings that may offer scenic views and access to nearby lakes or rivers. These properties often feature amenities such as spacious living areas, fully equipped kitchens, and outdoor decks for enjoying the natural surroundings.
How much does it cost to rent a holiday home in Winterwood?
Prices for holiday 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 holiday 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 rental amenities include fully equipped kitchens, allowing guests to prepare their own meals, as well as stunning mountain views that enhance the overall experience. Many rentals also feature patios, great for enjoying the fresh mountain air, and fireplaces that create a warm and friendly space during cooler evenings. Additionally, most properties come with coffee and tea makers, ensuring that guests can start their day with a warm beverage while taking in the picturesque surroundings.
Are there any family house rentals in Winterwood?
In Winterwood, Colorado, there are numerous family house rentals available, with around 73 options to choose from. This mountainous region is a fantastic spot for families, boasting a variety of spacious homes that cater to groups of all sizes. Many properties offer practical amenities such as fully equipped kitchens, allowing for convenient meal preparation after a day of outdoor adventures. Additionally, you can find homes with inviting living areas, outdoor decks, and sometimes even private hot tubs, superb for unwinding in the evenings.
Can I rent a holiday home with a pool or hot tub in Winterwood?
In Winterwood, Colorado, there are plenty of holiday homes available for rent that feature both pools and hot tubs, with around 21 properties offering pools and a top 72 with hot tubs. This picturesque area, located in the Rocky Mountains, provides a stunning backdrop for a getaway. Travellers can find rentals in various neighbourhoods, each offering unique charm and proximity to outdoor activities.
Are there any Winterwood holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winterwood 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.
Are there pet-friendly holiday rentals in Winterwood?
In Winterwood, Colorado, travellers can book a variety of pet-friendly holiday rentals, with around 18 options available to choose from. Many of these rentals offer convenient amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely.
Can I find long-stay holiday rentals in Winterwood?
A long-stay holiday rental in Winterwood 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 Winterwood for a holiday rental?
December is the most popular time to visit Winterwood, particularly for those seeking a festive getaway in the heart of the Rocky Mountains. This month falls within the peak season, which runs from November to January, attracting winter sports enthusiasts eager to hit the slopes. With an average temperature hovering around -4°C, visitors can expect a magical winter wonderland, great for skiing, snowboarding, and cosy evenings by the fire.

The holiday season brings a vibrant atmosphere to Winterwood, with plenty of opportunities for outdoor activities. Imagine gliding through freshly fallen snow or exploring the charming local shops adorned with twinkling lights. For those who enjoy a bustling environment, this is the time to be there, with fellow travellers sharing in the joy of the season.

If you're looking for a more budget-friendly experience, May offers a wonderful alternative. While this month is considered low season, it presents a unique opportunity to appreciate the beauty of Spring as the snow melts away, revealing lush landscapes and blooming wildflowers. It's an ideal time for hiking and enjoying the serene surroundings without the larger crowds, allowing for a more tranquil experience.
Are there any remote work holiday rentals in Winterwood?
In Winterwood, Colorado, there is a substantial selection of remote work-friendly holiday rentals available, with around 78 options to choose from. These properties are well-suited for those looking to combine work and leisure amidst the stunning mountain scenery. Travellers can expect amenities such as reliable Wi-Fi, dedicated office spaces, and comfortable desks, making it easy to stay productive during their stay. Many rentals also feature comfortable living areas to unwind after a day of work, and some may offer additional perks like computer monitors and ergonomic office chairs for an enhanced working experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Winterwood holiday rental?
Book your Winterwood 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 Winterwood home rental booking on Vrbo?
To find Winterwood 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 Winterwood 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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