669+ Rental Villas and Private Getaways in Winding Trail |
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Winding Trail Vacation Rentals & One Degree Stays Homes

About Winding Trail Vacation Rentals

There are more than 669 vacation rentals that are available in Winding Trail. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Winding Trail.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Winding Trail, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Winding Trail. Places to stay near Winding Trail are 1042.37 ft² on average, with prices averaging US $513 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Winding Trail with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Winding Trail

Type Count
Vacation Homes 413
Holiday Apartments 106
Cottages 9

Use these Quick Filters to Find a Vacation Rental in Winding Trail

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winding Trail.

Weather in Winding Trail, CO

View the weather forecast for Winding Trail before booking your Winding Trail Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Frequently Asked Questions About Winding Trail?

What are the top vacation rentals in Winding Trail?

There are a lot of options in Winding Trail. If you plan on staying in the Winding Trail area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winding Trail:

How many vacation rentals have private pools in Winding Trail?

There are 7 vacation rentals with private pools near Winding Trail. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Winding Trail are best for families?

If you are looking for a family-friendly vacation home in Winding Trail, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winding Trail:

How many onedegreestays vacation rentals are available in Winding Trail?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 669 in the Winding Trail area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Winding Trail. 

Nearby Neighborhood (5) 
Neighborhood Property Count
North Boulder Vacation Rentals in Boulder, Colorado 69
Glenwood Grove - North Iris Vacation Rentals in Boulder, Colorado 310
Rural North Boulder Vacation Rentals in Boulder, Colorado 439
Parkside Vacation Rentals in Boulder, Colorado 505
Palo Park Vacation Rentals in Boulder, Colorado 447

People Also Ask

There are 669 Winding Trail, CO Vacation Rentals

Recently Booked Vacation Rentals in Winding Trail