Top Trailhead Lodge Vacation Rentals

Explore a selection of Trailhead Lodge vacation rentals

Luxury Downtown Ski Condo - Family Friendly - Sunny South Facing...
Guests5
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$88 avg/night
1 bed
1 Bathroom
Guests 5
53 reviews
Luxurious Condo! Hideaway Park Concerts, Beautiful Trails...
Guests9
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$233 avg/night
3 beds
2 Bathrooms
Guests 9
16 reviews
Brand New! Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown...
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$229 avg/night
3 beds
2 Bathrooms
Guests 8
15 reviews
Enjoy Stunning Fall Colors From This Deck
Guests10
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$211 avg/night
3 beds
3 Bathrooms
Guests 10
36 reviews
Spacious 3 bedroom / 3 bathroom condo at the new property in the...
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$195 avg/night
3 beds
3 Bathrooms
Guests 8
28 reviews
One Block From All Restaurants And Shopping, Nightlife
Guests6
Bedroom1
Bathroom1
Wonderful 5 / 5
$117 avg/night
1 bed
1 Bathroom
Guests 6
89 reviews
Beautifully Furnished 2 Bedroom 2 Bathroom Condo In The Heart Of...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$151 avg/night
2 beds
2 Bathrooms
Guests 6
30 reviews
Luxury Model Unit w Hot Tub/Pool, Walk to Restaurants, Views of...
Guests9
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$259 avg/night
3 beds
3 Bathrooms
Guests 9
5 reviews
Winter Park Luxury Condominium and Mountain Getaway!
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$143 avg/night
1 bed
1 Bathroom
Guests 4
11 reviews
Luxury 2 Bed 2 Bath at Trailhead Lodge / Sleeps 7
Guests7
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$279 avg/night
2 beds
2 Bathrooms
Guests 7
10 reviews
3 Bed 2 Bathroom Brand New Condo 5 minute walk to free shuttle
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.6 / 5
$214 avg/night
3 beds
2 Bathrooms
Guests 8
5 reviews
NEW Winter Park condo in the heart of downtown
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$205 avg/night
3 beds
2 Bathrooms
Guests 8
12 reviews
Luxury 2B/2B Downtown Condo, faces Hideaway Park(stage/sledding...
Guests8
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$166 avg/night
2 beds
2 Bathrooms
Guests 8
27 reviews
2 bed/2 bath with bunk room sleeps 8 Winter Park
Guests8
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$239 avg/night
2 beds
2 Bathrooms
Guests 8
5 reviews
WP Condo -3 BR, with bonus bunk room. Walk to restaurants and...
Guests14
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$367 avg/night
3 beds
3 Bathrooms
Guests 14
2 reviews
Inquire about DISCOUNTED Sept & Oct 2017 Rates!! 2 BR in heart of...
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$165 avg/night
2 beds
2 Bathrooms
Guests 6
6 reviews
3 Bed 3 1/2 Bath with garage, hot tub and unbeatable downtown...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$250 avg/night
3 beds
2 Bathrooms
Guests 8
10 reviews
Centrally Located in Winter Park with Private Hot Tub. Perfect!
Guests10
Bedrooms3
Bathrooms3
Wonderful 4.8 / 5
$243 avg/night
3 beds
3 Bathrooms
Guests 10
6 reviews
NEW! 3BR Winter Park Condo w/ Hot Tub, Pool & View
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$179 avg/night
3 beds
2 Bathrooms
Guests 8
4 reviews
Trailhead Lodge Unit 811: 1 BR / 1 BA condominium in Winter Park...
Guests4
Bedroom1
Bathroom1
Wonderful 4.3 / 5
$125 avg/night
1 bed
1 Bathroom
Guests 4
3 reviews
Luxury Condo in Downtown Winter Park (2 bed, 2 bath, sleeps up to...
Guests9
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$233 avg/night
2 beds
2 Bathrooms
Guests 9
1 reviews
Perfect Package - King Bed, Pool, Hot Tub, Ski Shuttle & Shops...
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$163 avg/night
1 bed
1 Bathroom
Guests 4
4 reviews
Home Away from Home: Walk to pool, fire, hot tub, and HIdeaway...
Guests9
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$209 avg/night
2 beds
2 Bathrooms
Guests 9
Sled, Ski & Swim From This Winter Paradise With Pool!
Guests8
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$200 avg/night
2 beds
2 Bathrooms
Guests 8
2 reviews
Super Stylish With Great Views And 5 Star Reviews
Guests8
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$231 avg/night
3 beds
3 Bathrooms
Guests 8
3 reviews
Late summer rates decreased! Balcony view of Hideaway Park...
Guests8
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$144 avg/night
2 beds
2 Bathrooms
Guests 8
9 reviews
Amazing Condo in Downtown Winter Park!
Guests9
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$298 avg/night
3 beds
3 Bathrooms
Guests 9
1 reviews
Joanna Gaines Would Want to Stay Here: Barnwood, High End Touches...
Guests10
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$227 avg/night
3 beds
3 Bathrooms
Guests 10
1 reviews
Brand New Condo In The Heart Of Downtown. One Bedroom Plus Den!
Guests4
Bedroom1
Bathroom1
Wonderful 4.5 / 5
$186 avg/night
1 bed
1 Bathroom
Guests 4
4 reviews
Spacious, Stylish Trailhead Condo With BEST Hideaway Park Views
Guests7
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$200 avg/night
2 beds
2 Bathrooms
Guests 7
Take In The Shows, Swim In The Pool & Relax In Style: Trailhead...
Guests7
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$198 avg/night
2 beds
2 Bathrooms
Guests 7
3 BR/3.5 BA In the Heart of All The Adventures Of Winter Park...
Guests12
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$200 avg/night
3 beds
3 Bathrooms
Guests 12
1 reviews
One Bedroom Luxury Condo, Unit 831, Downtown Winter Park, Perfect...
Guests4
Bedroom1
Bathroom1
Wonderful 0 / 5
$126 avg/night
1 bed
1 Bathroom
Guests 4
Affordably Priced 1 Bedroom - Trailhead Lodge 811
Guests4
Bedroom1
Bathroom1
Wonderful 0 / 5
$113 avg/night
1 bed
1 Bathroom
Guests 4
Upscale 3BR In Town with Pool, Walking Distance To...
Guests8
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$324 avg/night
3 beds
3 Bathrooms
Guests 8
22 reviews
Winter Park Luxury Condominium and Mountain Getaway!
Guests6
Bedrooms2
Bathroom1
Wonderful 5 / 5
$171 avg/night
2 beds
1 Bathroom
Guests 6
16 reviews

Trailhead Lodge (Winter Park, CO, USA) Vacation Rentals

Luxury Downtown Ski Condo - Family Friendly - Sunny South Facing...

Luxurious Condo! Hideaway Park Concerts, Beautiful Trails...

Brand New! Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown...

Enjoy Stunning Fall Colors From This Deck

Spacious 3 bedroom / 3 bathroom condo at the new property in the...

One Block From All Restaurants And Shopping, Nightlife

Beautifully Furnished 2 Bedroom 2 Bathroom Condo In The Heart Of...

Luxury Model Unit w Hot Tub/Pool, Walk to Restaurants, Views of...

Winter Park Luxury Condominium and Mountain Getaway!

Luxury 2 Bed 2 Bath at Trailhead Lodge / Sleeps 7

3 Bed 2 Bathroom Brand New Condo 5 minute walk to free shuttle

NEW Winter Park condo in the heart of downtown

Luxury 2B/2B Downtown Condo, faces Hideaway Park(stage/sledding...

2 bed/2 bath with bunk room sleeps 8 Winter Park

WP Condo -3 BR, with bonus bunk room. Walk to restaurants and...

Inquire about DISCOUNTED Sept & Oct 2017 Rates!! 2 BR in heart of...

3 Bed 3 1/2 Bath with garage, hot tub and unbeatable downtown...

Centrally Located in Winter Park with Private Hot Tub. Perfect!

NEW! 3BR Winter Park Condo w/ Hot Tub, Pool & View

Trailhead Lodge Unit 811: 1 BR / 1 BA condominium in Winter Park...

Luxury Condo in Downtown Winter Park (2 bed, 2 bath, sleeps up to...

Perfect Package - King Bed, Pool, Hot Tub, Ski Shuttle & Shops...

Home Away from Home: Walk to pool, fire, hot tub, and HIdeaway...

Sled, Ski & Swim From This Winter Paradise With Pool!

Super Stylish With Great Views And 5 Star Reviews

Late summer rates decreased! Balcony view of Hideaway Park...

Amazing Condo in Downtown Winter Park!

Joanna Gaines Would Want to Stay Here: Barnwood, High End Touches...

Brand New Condo In The Heart Of Downtown. One Bedroom Plus Den!

Spacious, Stylish Trailhead Condo With BEST Hideaway Park Views

Take In The Shows, Swim In The Pool & Relax In Style: Trailhead...

3 BR/3.5 BA In the Heart of All The Adventures Of Winter Park...

One Bedroom Luxury Condo, Unit 831, Downtown Winter Park, Perfect...

Affordably Priced 1 Bedroom - Trailhead Lodge 811

Upscale 3BR In Town with Pool, Walking Distance To...

Winter Park Luxury Condominium and Mountain Getaway!