
Trailhead Lodge vacation rentals
We found 53 vacation rentals — enter your dates for availability
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Trailhead Lodge
Newly Updated TopFlr Views Of FootHills_River Private Balcony Hideaway Park
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
185 reviews(185 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)
Luxury Condo 414 I Pool I Club House I Hot Tub I Best Price I Discounted Attractions
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
135 reviews(135 reviews)
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
220 reviews(220 reviews)
Enjoy a front row seat to all Winter Park downtown activities!
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
166 reviews(166 reviews)
Live Music Views & Pool Oasis in Hideaway Park!
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
Top rated rentals - Trailhead Lodge
Great Place Great Location
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Great family friendly place to stay.
Clarissa A.
Stayed Aug 2025
Great Stay
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Great Experience, Host was very accommodating, my family loved it.
Andrew
Stayed Apr 2025
Ski Trip
1010 out of 10
Exceptionalexceptional
105 reviews(105 reviews)
Great property and location. Very convenient to shuttle bus to slopes and restaurants. Steve was a very responsive host.
Marshall B.
Stayed Mar 2025
Weekend getaway
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
We loved our stay here! It was very convenient and close to the ski area. The unit was clean and the parking was great.
Kathleen S.
Stayed Feb 2025
White Christmas Get Away
1010 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
This is our second time staying at the Trailhead Lodges and we loved it! The property was as described in the pictures. It had everything we needed for our stay. The location was unbeatable and the views were spectacular! Will definitely be back sooner than later!
Amanda M.
Stayed Dec 2024
A warm & comfortable visit, gorgeous views and spacious condo
1010 out of 10
Exceptionalexceptional
185 reviews(185 reviews)
We loved everything about this condo - super spacious, awesome living room/fireplace, gorgeous views, amazing kitchen. Even heated floors in the bathrooms! Our one sad thing was that the hot tub was broken the whole time and there was just the outdoor hot tub and pool - which in the summer would be amazing but in the winter meant we didn't really use the club house. For some reason I thought there was an indoor hot tub there but there's not - I think other reviews were talking about the Rec center pool and hot tub, which we ended up going to and was really cool. Overall an amazing trip though and we'd love to stay here again. By the way it's also walking distance to the downtown square- restaurants, bars, Hideaway park brewery, Christy sports, cute coffee places etc. We loved being able to walk over there! Oh and also the hosts were super responsive to all our questions and allowed us to check in early and check out late which was a huge help to us. Their responsiveness was reassuring and made it a wonderful stay.
Kristin S.
Stayed Mar 2024
Loved it!
1010 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
We loved this property! It was very comfortable and well stocked. Property is close to restaurants, shopping and ski resort. The condo is peaceful and quiet and balcony looks on a river. Property manager answered questions quickly. We’ll be back for sure!
Randa L.
Stayed Jun 2023
Everything You Need
1010 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
This condo was perfect for our family. Cleanliness is what is most important to me and the place was very clean, which made us all very comfortable. Good communication from rental agency, great location, our 2nd time at that condo complex, but first time at this condo. Loved the first floor location and tons of storage. We will rent again!
Stacy F.
Stayed Feb 2023
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value