648+ Vacation Rentals & Holiday Homes in Winding Trail |
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  3. Boulder
  4. Winding Trail

Winding Trail Accommodations - Hotels & Rentals

About Winding Trail Vacation Rentals

Discover More than 648 Incredible Getaway Rentals Available in Winding Trail. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Winding Trail.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Winding Trail, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Winding Trail. The Average Size of Places to Stay Near Winding Trail is 1066.16 ft², with Prices Averaging US $522 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Winding Trail. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Winding Trail

Type Count
Vacation Homes 399
Holiday Apartments 100
Cottages 9

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

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Winding Trail with Online Reservations.

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 hotels, lake houses & vacation rentals in Winding Trail?

We provide an array of great vacation destinations in Winding Trail. If you are looking to stay in or around the Winding Trail area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Winding Trail:

How many Hotels & Vacation Rentals have private pools in Winding Trail?

We have 5 Hotels & Vacation Rentals featuring a private pool in and near Winding Trail. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Winding Trail is best for families?

Searching for a family-friendly getaway in Winding Trail? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Winding Trail?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 648 in the Winding Trail area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Winding Trail.

Nearby Neighborhood (5) 
Neighborhood Property Count
North Boulder Vacation Rentals in Boulder, Colorado 67
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

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