Trailhead Lodge holiday homes
We found 52 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Trailhead Lodge
Showing deals for:14 Nov - 21 Nov
Image gallery for Modern and spacious 1 bdrm condo - walk to everything in downtown Winter Park!
1010 out of 10 rating
Exceptional
(66 reviews)
Modern and spacious 1 bdrm condo - walk to everything in downtown Winter Park!
Winter Park, CO
8% off
Price is NZ$5,630
NZ$5,630
NZ$804 per night
includes taxes & fees
Image gallery for Luxury Condo 613 I Pool I Club House I Hot Tub I Views I Best Price I Discounted Attractions
1010 out of 10 rating
Exceptional
(35 reviews)
Luxury Condo 613 I Pool I Club House I Hot Tub I Views I Best Price I Discounted Attractions
Winter Park, CO
5% off
Price is NZ$3,865
NZ$3,865
NZ$552 per night
includes taxes & fees
Image gallery for Luxury Condo 412 I Pool I Club House I Hot Tub I Views I Best Price I Discounted Attractions
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Luxury Condo 412 I Pool I Club House I Hot Tub I Views I Best Price I Discounted Attractions
Winter Park, CO
5% off
Price is NZ$3,865
NZ$3,865
NZ$552 per night
includes taxes & fees
Image gallery for Luxury Condo 224 I Pool I Club House I Hot Tub I Views I Best Price I Discounted Attractions
9.49.4 out of 10 rating
Exceptional
(18 reviews)
Luxury Condo 224 I Pool I Club House I Hot Tub I Views I Best Price I Discounted Attractions
Winter Park, CO
5% off
Price is NZ$5,653
NZ$5,653
NZ$808 per night
includes taxes & fees
Image gallery for 3BR Condo w/ Pool, Downtown, easy Shuttle Access, across from the Event Center.
1010 out of 10 rating
Exceptional
(8 reviews)
3BR Condo w/ Pool, Downtown, easy Shuttle Access, across from the Event Center.
Winter Park, CO
7% off
Price is NZ$4,838
NZ$4,838
NZ$691 per night
includes taxes & fees
Image gallery for Luxury Condo with Hot Tub, Pool, & Private Patio in the Heart of Winter Park!
1010 out of 10 rating
Exceptional
(37 reviews)
Luxury Condo with Hot Tub, Pool, & Private Patio in the Heart of Winter Park!
Winter Park, CO
14% off
Price is NZ$3,377
NZ$3,377
NZ$482 per night
includes taxes & fees
Image gallery for The Adventure Loft! Free ski shuttle and sledding hill! Walk to restaurants!
1010 out of 10 rating
Exceptional
(33 reviews)
The Adventure Loft! Free ski shuttle and sledding hill! Walk to restaurants!
Winter Park, CO
7% off
Price is NZ$3,824
NZ$3,824
NZ$546 per night
includes taxes & fees
Image gallery for "The Lazy Z @ Winter Park”: On the Fraser River & Downtown!
1010 out of 10 rating
Exceptional
(47 reviews)
"The Lazy Z @ Winter Park”: On the Fraser River & Downtown!
Winter Park, CO
11% off
Price is NZ$5,405
NZ$5,405
NZ$772 per night
includes taxes & fees
Image gallery for Walk to Main Street! Large Cozy Multi-Family Condo, sleeps 14. 3 BR, with Den.
1010 out of 10 rating
Exceptional
(40 reviews)
Walk to Main Street! Large Cozy Multi-Family Condo, sleeps 14. 3 BR, with Den.
Winter Park, CO
7% off
Price is NZ$5,152
NZ$5,152
NZ$736 per night
includes taxes & fees
Image gallery for Perfect spot for Fall Events in Winter Park. TOWP STR Permit #006902
1010 out of 10 rating
Exceptional
(75 reviews)
Perfect spot for Fall Events in Winter Park. TOWP STR Permit #006902
Winter Park, CO
7% off
Price is NZ$2,985
NZ$2,985
NZ$426 per night
includes taxes & fees
Image gallery for Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!
1010 out of 10 rating
Exceptional
(69 reviews)
Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!
Winter Park, CO
7% off
Price is NZ$3,364
NZ$3,364
NZ$481 per night
includes taxes & fees
Image gallery for Sledding Hill Views! Steps to dining & shops!
1010 out of 10 rating
Exceptional
(105 reviews)
Sledding Hill Views! Steps to dining & shops!
Winter Park, CO
8% off
Price is NZ$5,084
NZ$5,084
NZ$726 per night
includes taxes & fees
Image gallery for Luxury Condo 414 I Pool I Club House I Hot Tub I Best Price I Discounted Attractions
1010 out of 10 rating
Exceptional
(135 reviews)
Luxury Condo 414 I Pool I Club House I Hot Tub I Best Price I Discounted Attractions
Winter Park, CO
6% off
Price is NZ$4,053
NZ$4,053
NZ$579 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Trailhead Lodge
Enjoy front row seat to all Winter Park downtown activities.
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
164 reviews(164 reviews)
Lux 2B/2B Dwtn Condo w/ clubhouse, faces Hideaway Park stage/sledding hill,WiFi
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
Downtown 2BR condo w/ balcony & heated pool
Sleeps 8 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Newly Updated TopFlr Views Of FootHills_River Private Balcony Hideaway Park
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
182 reviews(182 reviews)
3 Bed 3 1/2 Bath with garage, hot tub and unbeatable downtown location
Sleeps 8 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
67 reviews(67 reviews)
Live Music Views & Pool Oasis in Hideaway Park!
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value