Trailhead Lodge vacation rentals
We found 52 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Trailhead Lodge
Showing deals for:Nov 14 - Nov 21
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
7% off
Price is CA $343
CA $343
CA $3,159 total
CA $3,159 total
includes taxes & fees
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
10% off
Price is CA $495
CA $495
CA $4,600 total
CA $4,600 total
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
(20 reviews)
Luxury Condo 412 I Pool I Club House I Hot Tub I Views I Best Price I Discounted Attractions
Winter Park, CO
7% off
Price is CA $333
CA $333
CA $3,060 total
CA $3,060 total
includes taxes & fees
Image gallery for Trailhead 232 pool, hot tub, clubhouse
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Trailhead 232 pool, hot tub, clubhouse
Winter Park, CO
5% off
Price is CA $174
CA $174
CA $2,082 total
CA $2,082 total
includes taxes & fees
Image gallery for Trailhead 322 Shared Hot Tub, Pool, Private Balcony, and Grill
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Trailhead 322 Shared Hot Tub, Pool, Private Balcony, and Grill
Winter Park, CO
5% off
Price is CA $874
CA $874
CA $8,173 total
CA $8,173 total
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
10% off
Price is CA $407
CA $407
CA $3,978 total
CA $3,978 total
includes taxes & fees
Image gallery for Trailhead 721 Pet Friendly pool hot tub
1010 out of 10 rating
Exceptional
(31 reviews)
Trailhead 721 Pet Friendly pool hot tub
Winter Park, CO
5% off
Price is CA $174
CA $174
CA $2,032 total
CA $2,032 total
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
7% off
Price is CA $487
CA $487
CA $4,478 total
CA $4,478 total
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
10% off
Price is CA $314
CA $314
CA $3,125 total
CA $3,125 total
includes taxes & fees
Image gallery for Trailhead 212 Downtown walk to bars, restaurants
9.69.6 out of 10 rating
Exceptional
(26 reviews)
Trailhead 212 Downtown walk to bars, restaurants
Winter Park, CO
5% off
Price is CA $210
CA $210
CA $2,384 total
CA $2,384 total
includes taxes & fees
Image gallery for Trailhead 524 Clubhouse w/ Hot tub | Pool
9.89.8 out of 10 rating
Exceptional
(46 reviews)
Trailhead 524 Clubhouse w/ Hot tub | Pool
Winter Park, CO
5% off
Price is CA $227
CA $227
CA $2,728 total
CA $2,728 total
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
15% off
Price is CA $462
CA $462
CA $4,417 total
CA $4,417 total
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
19% off
Price is CA $279
CA $279
CA $2,767 total
CA $2,767 total
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
10% off
Price is CA $433
CA $433
CA $4,211 total
CA $4,211 total
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
10% off
Price is CA $248
CA $248
CA $2,438 total
CA $2,438 total
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
10% off
Price is CA $279
CA $279
CA $2,750 total
CA $2,750 total
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
10% off
Price is CA $442
CA $442
CA $4,156 total
CA $4,156 total
includes taxes & fees
Image gallery for Trailhead 812 Pet Friendly Downtown Winter Park
9.69.6 out of 10 rating
Exceptional
(40 reviews)
Trailhead 812 Pet Friendly Downtown Winter Park
Winter Park, CO
5% off
Price is CA $214
CA $214
CA $2,537 total
CA $2,537 total
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
7% off
Price is CA $349
CA $349
CA $3,208 total
CA $3,208 total
includes taxes & fees
Image gallery for Trailhead 211 shared hot tub
1010 out of 10 rating
Exceptional
(44 reviews)
Trailhead 211 shared hot tub
Winter Park, CO
5% off
Price is CA $230
CA $230
CA $2,705 total
CA $2,705 total
includes taxes & fees
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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)
Top rated rentals - Trailhead Lodge
WP Condo
1010 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
Great, clean property. Kitchen was well stocked. Great to have private hot tub. We'll definately stay here again.
Eric C.
Stayed Dec 2020
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, yards and more
More for lessMore space, more privacy, more amenities — more value