Trailhead Lodge holiday lettings

We found 56 holiday rentals — enter your dates for availability

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November 2025

December 2025

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Find the best place to stay - Trailhead Lodge

Showing deals for: 23 Feb - 26 Feb

Premier Host

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

Sleeps 8 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

£341 per night

includes taxes & fees

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

for 3 nights, 1 apartment

£321 per night

includes taxes & fees

NEW! 3BR/3BA Penthouse Downtown, Htd Pool/Hot Tub next to park and playground

Sleeps 9 · 3 bedrooms · 3 bathrooms

for 3 nights, 1 apartment

£647 per night

includes taxes & fees

Living Area - Flat screen TV, fireplace, large windows, and natural lighting.

Premier Host

Luxury Condo at Standard Pricing. Overlooking Hideaway Park. Pool & hot tub

Sleeps 8 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

£337 per night

includes taxes & fees

Premier Host

Trailhead Lodges 514 | Stellar Views from Balcony | Walk To The Best Restaurants

Sleeps 10 · 3 bedrooms · 3 bathrooms

for 3 nights, 1 apartment

£408 per night

includes taxes & fees

Top rated rentals - Trailhead Lodge

Deck Looks down on Hideaway Park for Sledding and Summertime live music Events

Premier Host

Christmas Skiing

A great property, well located and well equipped, however, I did think this was over priced from my previous experiences of renting properties in Winter Park.

Ian M.

Stayed Dec 2021

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