Trailhead Lodge holiday rentals

We found 57 holiday rentals — enter your dates for availability

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December 2025

January 2026

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Find the best place to stay - Trailhead Lodge

Premier Host

Lux 2B/2B Dwtn Condo w/ clubhouse, faces Hideaway Park stage/sledding hill,WiFi

Sleeps 8 · 2 bedrooms · 2 bathrooms

Living room - Additional seating at the kitchen island.

Premier Host

Luxury condo in the heart of Town of WP. Access to pool, hot tub & pool table

Sleeps 8 · 2 bedrooms · 1 bathroom

Premier Host

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

Sleeps 6 · 2 bedrooms · 2 bathrooms

Kitchen. Island leads extra seating for family and friends

Perfect spot for Winter activities. In Winter Park CO.TOWP STR Permit #006902

Sleeps 7 · 2 bedrooms · 2 bathrooms

Top rated rentals - Trailhead Lodge

Trailhead

The property was well appointed , clean and extremely spacious. It was close to the shops and restaurants and easy access to winterpark resort via the bus

Ross P.

Stayed Jan 2023

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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value