Trailhead Lodge, Winter Park holiday accommodation: short-term house rentals & properties

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Trailhead Lodge

Warm up in front of the gas fireplace after skiing at the Winter Park Resort

Premier Host

Trailhead 232 pool, hot tub, clubhouse

Sleeps 4 · 1 bedroom · 2 bathrooms

Premier Host

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

Sleeps 6 · 2 bedrooms · 2 bathrooms

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

Sleeps 9 · 3 bedrooms · 3 bathrooms

Welcome To The Stunning Trailhead Condo #414

Premier Host

Luxury Condo 414 I Pool I Club House I Hot Tub I Best Price I Discounted Attractions

Sleeps 6 · 2 bedrooms · 2 bathrooms

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

Top rated rentals - Trailhead Lodge

Kitchen. Island leads extra seating for family and friends

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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All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value